Five NBA Playoff Takes, Plus David Letterman’s First-Ever BS Pod Appearance (We Did It!!!)

26:26Bill Simmons:Nick Wright and I talked a lot about it on Tuesday's pod and whatever. It was a recipe for a blowout. I didn't see it. I thought Minnesota was going to show up, but they got the game they needed to get. A couple of mailbag questions, then we'll get to Letterman. This is from Frank. You did the lottery karma rankings and mentioned the Heat not having a top 10 pick since 08. You mentioned the BAM 83-point game. But the biggest karma coming Miami's way is Miami getting screwed on the Rozier trade, only getting a measly second round pick back. The league left them in limbo for months and then ruled that Miami couldn't even get its own first back.

27:03Bill Simmons:Could that incentivize the basketball gods to sprinkle enough karma to grant them a top four pick this year? That's from Frank. You know what? When I'm wrong, I'm wrong. I should have thought of this. They really got screwed on that Rozier thing. They traded for a guy who is now under a federal felony investigation for point shaving and, um, for stuff that he did when he was on the Hornets. So, um, yeah, I, I, I have to adjust my rankings. I still have Indiana first Atlanta second, Washington third. I think Miami's fourth. Cause I forgot about the Rozier trade. I think that's a lot of lottery karma points.

27:42Bill Simmons:So thanks to Frank for, uh, pointing that one out. This comes from Morgan Taylor. who is a toronto raptors fan and he says a messiah you harry stan and he says my biggest fear now as a raptors fan is that yannis asked to go to dallas and in the opening press conference yannis comes out and says he's always wanted to play for messiah these guys have had a long time relationship and and when it when we first thought yannis might be available toronto was always a team morgan says i really felt like toronto had a solid chance of landing him up until they fired the best exec in the NBA to save a few bucks.

28:16Bill Simmons:Thoughts? I hadn't thought of this. I've been very focused on Giannis, Jalen Brown trades, and whether it made sense to trade for Giannis and how many years he could have left here at an elite level with a lot of miles on him and a lot of injuries last year. And I didn't even realize Boston might not even be the main contender. The Dallas thing makes a ton of sense. If I'm Dallas, I have that pick, which we'll see what happens in the lottery, but they're going to be somewhere between one and eight. I think they have like a 35, 36 % chance of moving to the top four. But let's say it's going to be six, seven, eight range, which will still be a really good player in this draft.

28:54Bill Simmons:And I think a nice trade thing. I was trying to figure out things they could do and things Milwaukee would want. And one thing that would really help, ironically, the Celtics had this giant$28 million trade exception. So they could take Daniel Gafford in the trade because they need another center. and he's making almost 20 million a year, send Hauser back to Dallas into the trade exception they have. So Dallas would save 10 million there and then be able to add Giannis. And then Milwaukee, they would get the Klay Thompson, Najee Marshall expirings, Max Christie, Dallas is 2026 first, OKC's 2026 first, because they have that end of the round, but still.

29:36Bill Simmons:And then they have the Lakers 29 first to maybe throw in a swap there. And the only reason I don't think they would do this trade, Milwaukee, is because they don't have control of their picks the next five years. So just doing a trade for picks and to save money, basically, doesn't help the situation of, well, what happens if we have a top three worst team next year and we don't have our pick? But it is interesting. So I wonder what would be the tipping point of picks and stuff, Dallas would have to throw in there. If I'm Dallas, I'm doing everything I can to end up with Kyrie, Cooper, Flag, and Giannis, you know, within reason.

30:17Bill Simmons:And if it doesn't happen, it doesn't happen. But really interested to see what Giannis' trade value is and how desperate teams are to go after him. And, you know, we've been talking about it for nine, 10 months. But I think a lot of teams are looking at this the same way. Guy's been in the 2013 draft to now, 13 years, hasn't really been 100 % healthy through a season for a few years now. And what are you trading for? And how much do you want to trade for the risk of this could be Dwight Howard in the mid 2010s for all we know. Thinking about that with my team. I think the reason the Celtics would think about it is Jalen's got the three huge years left.

30:54Bill Simmons:Giannis has one huge year left. You add an extension to that. So the money would be around the same. And then you would hope you get lucky. If you saw Brad Stevens' press conference, He was not happy with the playoff series, how the team played, being as three-point happy as they are. He mentioned dunks multiple times and mentioned just being more physical. And it just, it felt like he was laying a lot of breadcrumbs to a Giannis trade. So we'll see. This could end up being, Giannis, I think the teams will keep adding to the list as more and more teams have unhappy endings to their season. Tom from Toronto.

31:29Bill Simmons:This is the last one I'll do. Oh, I got two left. Tom from Toronto want to know, has there ever been more of a peak time for local sports radio content in Boston? Thank God I'm not there right now. From Vrabel to Jalen to the Red Sox, just hot topics all around. Has any other time beaten it? So right now for sports radio topics, and you have to understand Boston sports radio, which is notoriously horribly negative and always glass half full at all times. So this is like a goldmine. You have the Celtics choking in round one. Joe Maz ran Tatum into the ground. Does Jalen want out and fake Giannis trades?

32:03Bill Simmons:So that's the smorgasbord right there. The Red Sox just fired their manager. Their GM's a robot. They have the curse of Mookie Betts. They have one since 2018 now. They've been 20 dumb moves and everyone wants John Henry to sell. Fodder all the way around. Bruins, 15-year cup draft, wasting pasta's career. He's 30 years old now. They just got screwed over in the lottery where if the Maple Leafs pick dropped one spot, they got the sixth pick in the draft and said the Maple Leafs won the lottery. Um, so you have that. And then you have the Patriots embarrassing Superbowl loss. You can do the, were they ever good all along fourth play, fourth play schedule to first place schedule.

32:39Bill Simmons:Um, Drake may did you rope a dope us? You have all that. You have the AJ Brown trade, and then you have Vrabel, the head coach in the Lincoln Patriots being involved in one of the two or three craziest Boston scandals ever for sports. Um, so there's that. so I went through all the years of my head and I settled on a year. The only one I could think of that was as kind of loaded as this one, 1996. So I'm talking winter 96 into 1997, um, which was one of the worst winners to live in Boston, just in general. I think we had like four blizzards that year, but we had the Patriots made the Superbowl and then Parcells, um, decided he, um, was on his way out.

33:25Bill Simmons:He wasn't going to coach the team. So breaking up with Kraft to make the Super Bowl, find out that he was maybe even planning to do the Jets. And so we had that. Everyone, everyone's taking sides. People are playing with Kraft, Parcells, unbelievable talk radio topic. And the Super Bowl loss. You had the Celtics who were in full tank mode at that point for Tim Duncan. And Tim Duncan's playing college basketball. You had the Bruins, who were the worst team in the league that year. They ended up tanking as well. and then you had Clemens leaving the Red Sox and drawing the ire of everybody. We were so mad.

33:59Bill Simmons:I think my second or third piece ever for ESPN in 2001 was called Is Roger Clemens the Antichrist? Also, the Yankees just won the World Series. So if you're just talking about like a dark, dark, dark place for Boston fans, I think 96 was worse. You know, we've had a lot of good stuff happening with the Boston teams, but this is a lot of fodder, which leads to my last email from Zach in Parkland, Florida, is the big winner out of the Vrabel-Rosini scandal, actually Drake May. Had a terrible playoff run capped with a Super Bowl performance that would have followed him all offseason. However, Vrabel, like a true leader, has completely taken that burden off his young QB.

34:38Bill Simmons:Even if May starts off slow next year, it's almost a guarantee that Vrabel will still be shouldering the blame due to the chaos he has caused. Zach from Parkland. Finally, a silver lining in the Vrabel-Russini scandal.

34:55Bill Simmons:This story, I did a whole thing, I think two, three weeks ago about how crazy this story was. And every time I think it's over, something else happens leading to what happened today, which was TMZ video of a seven months pregnant, Diana Rossini, going on a clandestine boat trip in Tennessee with Mike Vrabel. while she was carrying her future son, Michael.

35:27Yeah.

35:29Bill Simmons:This is a fucking crazy story. I don't, this is the first time I talked to my dad today where we were like, can he still coach the team? Like this is, is he gonna take a leave of absence? Is more stuff gonna come out?

35:48Bill Simmons:there's video of them on a boat trip in 2001 at 2021 i i just it feels like every day there's three social media clips of her on some podcast and rabel's somehow on the show too or she's talking about her husband this is like this story's a nightmare i feel so bad for everybody um involved and yet you can't look away it's like a car accident um and honestly i used to have this thing the tyson zone when any story i think i started in the early 2000s where the tyson zone got to the point where you would just believe any story about mike tyson you'd be like mike tyson got in a fight with a zombie bat and bit the bat's head off you're like i believe it um i'm hitting that point with this russini vrabel story i don't i went from i don't want to talk about this at all to being like, wow, we're, we might lose our coach.

36:44And I guess the only reason we wouldn't is, um, you know, our owner hasn't exactly,

36:50Bill Simmons:doesn't have a clean slate of things that's happened with him either. Maybe he'll be a little more forgiving, trying to be nice. Um, just a bonker story. I don't have anything else to say. I just hope no more videos come out, please. I'm tapping out. I'm tapping out. I'm like, I'm like, I need Arnold Scalant to throw. I'm in the camel clutch with the Iron Sheik. I need Arnold Scalant to throw the white towel and then save me. I really need to tap out from this Ray Burrini story. Please no more. Please. Please. We're going to take a break. We're going to come back with my hero, David Letterman.

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39:28Bill Simmons:David Letterman is here. I can't believe it. I can't believe it either, Bill. Thank you very much. We talked about this forever. Thanks for inviting me. I really appreciate this. I feel honored in some respect. Inviting you. You needed to invite yourself because this was up to you. I'm just so glad you're here. Yeah. Oh, well, now I feel less important if I invited myself in here. But thank you for having me. Thank you for tolerating me. And thank you for whatever we have ahead of us. So you were here for LA for... Well, Netflix is a joke. You did a thing Right. Oh, yeah. We talked to John Mulaney last night.

40:02I don't know. I just love the kid. He's tremendous. He's so nice. He's so bright. He's so funny. He's so multi-talented. And I think he would make it difficult for other comedians in his group because he is the guy to chase, boy. Do you feel like he's somebody that in any era he would have been exactly as successful? I think you're right. I think you alluded to that earlier, and I think that does apply to him because he doesn't seem to be locked into the 2020s. He could have been in the 1990s and earlier, for heaven's sakes. So you have a son in college. I do have a son in college. This is like working with Kreskin.

40:46Bill Simmons:Well, I have a daughter in college, but I have the daughter in college and a son who's a senior in high school. Yeah. How much have you learned from comedy and content just through your son? Not much. He doesn't give any tips? Very little. I don't know how to describe him. He's not forthcoming. He's not standoffish. He just would rather not share with his father. Interesting. Yeah. I'm always badgering my kids. What are you watching? What do you care about? Yeah. Who are the people? Well, I badger my son as well, but the response is always, yeah, what do you care? so i will say he frightens me from the time he was born i've been afraid of him because in the beginning i was fearful that i would do something that might damage him yeah and i kept cautioning his mother i said don't drop him because you hear these stories about infants being dropped she said oh don't worry i'm not going to drop him so i'm at work one day and i get a call in the middle of the day oh i'm so sorry i dropped the baby i said oh well good christ there you go you've Drop the baby.

41:53Congratulations.

41:55Bill Simmons:Baby was obviously okay. Yeah, the baby is okay. Unless that's the reason he has that attitude toward his father. I'm not sure. He ought to be angry with his mother, for God's sake. I'm still angry with his mother. You had all this stuff. I mean, how old were you when your son was born? You're in your mid-50s, right? Later? I think I was 57. Is that what I was? Oh, my God. It's just stupid. but I'm trying to imagine what my life would be like now if I had a baby and I don't know, I'm so set in all of these different structural ways. Sure. Just introducing that. Well, that was my reluctance up until the time I realized we better do this now.

42:33Right. Uh, and then it became the best thing I ever did in my life. I know every parent feels that way, but I certainly shared that. And then great regret about it, not having done it earlier.

42:44Bill Simmons:Well, when you did your retirement show and you told that whole story about you were out looking at birds with your son and there was this bird, you couldn't figure out what the bird was. And you came back and with the way you set up that story, and I just was watching it when it was happening, like, oh my God, is he setting up the retirement? Because there was like real thought put in behind. I'm telling you this story because this is now becoming more important to me than this show, these little moments with my son. That's right. And I thought that was a pretty good device. I'm not sure if you took it to court, it would hold up.

43:19But at the time, it served a purpose.

43:22Bill Simmons:How difficult was that show for you? Because I thought that was one of the four or five best shows you ever did. Because you knew the weight of it, nobody else did. Yes, you're very kind. And here we go. But thank you. Thank you very much, Bill. Let's talk more about you. No, I want to hear about the show, though. How hard was it to know you were going to do that? Um, there were so many other things tangential to that moment in my life. It was not difficult. And I had been doing it for three decades, more or less every night. So the part of me, the internal mechanism felt like, Oh, you don't worry.

43:58You're going to continue this without knowing it. It's like getting out of a car that's still moving. I just assumed, Oh yeah, Now there'll be more of these. So the, the real difficulty of it didn't set in for about, I don't know, a year, two, three years, well, two years because everything had been programmed for me. I was taken care of and I didn't, I wanted for nothing. I, whatever that is, I didn't want for anything. So I didn't, I just assumed to keep going. So it wasn't difficult. because there's this moment when you actually said it where it felt like yeah there was like

44:36Bill Simmons:two seconds for like oh my god it's the words have left my mouth yes i was more concerned with telling the story than i was with what those words meant right the result because it was television and there's a certain artifice about television as we all understand so um there was nothing personal about it it was a piece of business right yeah because you grew up i will not grew up, but when you were a young adult, idolizing Carson, which I did as well. Yeah. And Carson left and he was gone. I don't even know if he has an IMDb credit after the Tonight Show. He was just, we never saw him again. Yeah.

45:11I was sorry. There was a fellow who was a comic of some success and he loved Johnny Carson and he was out in Marina del Rey after the retirement. And Johnny's boat was anchored in a slip there at Marina del Rey. And as he's walking down the dock, he sees Johnny in a chair on the dock reading the newspaper. Well, now he's crazed because, my God, there's Johnny. And he starts calling Johnny because it's after Johnny has retired. And he wants an interaction with Johnny. And Johnny recognizes that he's being called, stands up, holds up the newspaper, and goes below decks. That was it. That was it, yeah.

45:53I just love that. There are a million stories of friends of mine who have had interactions with Johnny where it was like, poof, and he's gone. Wait a minute. Johnny was just here. Now he's gone.

46:05Bill Simmons:He's doing the Irish goodbyes. Exactly. He came on your show after he retired, which was great. That was a significant thing. And I think that was the last thing he ever did. Might have been. Might have been. Yeah, might have been. But also not surprising, at least in his case. Well, the fact that he went away just cold stone, goodbye, good night, I'm not coming back. I found that troubling a little bit. And I can't imagine that of happening for myself. Not that I can make that comparison to Johnny. But suddenly you stopped doing something. And he really did. But I could never have done that. I had to keep doing stuff.

46:46Bill Simmons:That's why I brought that up. Because part of me thought you were just going to be like that. We'd never see you again. You'd be living wherever. I kind of wish I was that guy, but I'm just not. There's a lot of people from, I would say, your generation who are still going at either the same rate or a slightly reduced rate. But like, Lauren is still doing SNL. He's over 80 now. Howard Stern just re-upped for three years. Larry David, who left Curb, I think. I don't know if Curb's going to come back, but now he announced this HBO show. and I actually asked Larry, like, I thought you were done. Why are you?

47:24Bill Simmons:And he's like, what am I going to do? I still love doing it. And that was his attitude. No, uh, the real trick when I was a kid, when everybody was a kid, was it 55 was retirement age or 60, 65, something like that. What a joke that is because you get to that or to the threshold of that. And you realize, Holy crap. I have, I have nothing beyond this. What am I going to do? So if you're productive and happy, just keep going for God's sakes. And I understand this is no great revelation, but it's what I experienced. And I think it's just what you described there. Yeah. And some people, people, a lot of times will say like the people who keep going and keep going and keep going, they end up living longer anyway.

48:04Bill Simmons:Oh, is that right? People that, you know, basically, all right, I'm done. I'm just going to play golf. Like that's when you get into trouble. Yeah. That doesn't work, does it? Yeah. No, you have to have interaction. You have to be doing things. and you like to think of, I love having ideas and all my life I've had trouble taking them from being ideas to fruition. And you can have a billion ideas and when they're ideas, they're the same size. So when they're that size of an idea, everything is manageable. And I have trouble getting it to the stage where, well, how do we do this? How in fact do we change it from something you manage in your head to an actual occurrence.

48:46Bill Simmons:I can identify with that. Well, I don't think so. No, I'm good at having ideas and sometimes not good at executing them. You look around your life and it seems to me like you've had very little trouble executing ideas. I've had some help. I've had a lot of good people around. Yeah, what you said about people retiring at 55, I feel like the curve is totally screwed up now. You know, because if you think about the way life was 50 years ago, people didn't even really expect to live past 60, right? All the ways things were different. I even think about this with horse racing. Somebody, I saw somebody had this great point about how much people used to care about horse racing because horses were part of our lives.

49:26Bill Simmons:Yeah. Oh, that's right. And now in the 2020s, how many horses, people with horses do you even know? That's right. They were integral to existence in the world. And then the sport that transformed them as a recreation for us. Yeah. It never occurred to me that that's the origin of that. Yeah, now it's like been replaced by cars, and people care more about F1 than horse racing because people identify with cars. I have this thing I brought you. I saw a documentary with your name on it about yacht rock music. Yeah, that was one of my two years ago. And I'll just tell you about yacht rock. This was the music when I went to California, Southern California.

50:06It was KNX-FM, and that's all they played, the mellow sounds of Southern California. And it pretty much was all what we now know of as Yacht Rock. And I thought it was trifling and didn't have much interest in it as serious music. And then I saw how it was kind of dissected and discussed on that documentary. And I realized, no, wait a minute, these guys were really up to something pretty good. High quality stuff. And I'll tell you what's been a problem for me. If you have the serious radio and you dial up Yacht Rock, they have some stooge, some cartoon character pretending he's some snobby, wealthy, superficial asshole enjoying Yacht Rock.

50:47And it's not for the people. It's only for the elite. I hate that guy and is what poisoned Yacht Rock for me until I saw your documentary.

50:55Bill Simmons:Oh, thank you. And then I, once again, I had real respect for it. It was great. I enjoyed that. One of the things I love, thank you. One of the things I loved about that idea, it was an era as it was happening. Nobody realized it was in error until like 15 years later. Yeah. Those are the best ones because we're actually telling a story of all these people didn't realize they were part of something. They felt marginalized in the bigger picture of rock. I just thought it was California when I got out there. That's all I listened to. And it was delightful. And then later when it was given this label, and I understand how the label was applied.

51:30Yeah. These, these, as I learned on your documentary, but then this moron on Sirius XM with that bullshit accent about, I'm upper crust, I'm East Hampton. This is what appeals to me. Can you do that? You can do that. You can make people disappear.

51:47Bill Simmons:My big passion is when they play Yacht Rock music that's not Yacht Rock on the Yacht Rock channel. Bread is not Yacht Rock. Just stop. Air supply is not Yacht Rock. Get them off. And then listen to this. Of course you'll listen to it. you're sitting right over there. And the producer didn't bother coming in. When I had a morning show on NBC and I knew a friend who was a friend of Irving Azoff. And in those days, Irving Azoff, I think before he became a flat out criminal crook in the world of music. And by the way, if I've got the facts of this wrong, I'm sorry. They said, well, we can get Michael McDonald if you want Michael McDonald to write your theme music.

52:31Oh my God. Yeah. Oh my God is right. And I said, you're kidding me. And they said, nope. And sure enough, Michael McDonald wrote the theme music to our morning show. And now having seen him as the integral iconic. The king of Yacht Rock. King of Yacht Rock. Now I'm eager. We have this piece of music that he wrote for us a thousand years ago. And here's another idea. I would like to use that somehow. So if you have any ideas, and by the way, I think he must still, no, of course he doesn't own it. Irving Azoff must own it. Oh, Jesus. But use that on something.

53:08Bill Simmons:Yeah, we couldn't get Steely Dan to be in the Yacht Rock thing because they hate the Yacht Rock label. They feel like they weren't Yacht Rock people, like really genuinely hate it. Well, let's call it something else for the love of God. Yeah. I mean, the mellow sounds of Southern California is what I identified it as. Yeah, so we finally talked him into it, but only if he got to trash Yacht Rock as the interview he did for the Yacht Rock. And then he cleared all the music for it. Because really, they set up that Southern California sound that became Yacht Rock. So we had to have them documentary.

53:40So anyway, here, when I saw your name on producing things, and I knew you were the genius behind 30 for 30, and this came across my desk, Jimmy Murphy, American Icon. Take a look at that and see if you can do anything with that. Jimmy Murphy, American icon.

54:01Bill Simmons:All right, I'm going to look at it. Okay. Give me the pitch, though. Give me the... Well, he's the only American to ever won a Grand Prix race in an American-built car. That's not true. He's one of two. The other one was Dan Gurney. He won the Belgian Grand Prix in a car that his company built. And this man, Jimmy Murphy, won the French Grand Prix back in the teens, I believe, in a Duesenberg. which was built in the United States. Two men have won races in the F1 system in American-built cars. And this is in the era of board tracks, when you would have oval courses, oval tracks, and they were all made of wood.

54:42The track surface was wooden. Highly perilous because of, guess what? Splinters. Who would have thought? Interesting, right. But he was a true icon and went over to France. And the French disliked him because he won so handily, even though his car was falling out from under him. And they were going to disqualify him because, well, sure, he won, but can he drive it home? And they said, well, no, he can't drive it home, but he still won the race. And other drivers in the event protested on his behalf and said, good Lord, the man won the race. Who cares if he could drive it home? Just typical of the French.

55:18You feel that way? I do as well.

55:20Bill Simmons:because the NBA, Victor Rambinjamba is going to take over, 7 '7", French guy. And I'm a little nervous because we've had a mixed checkered history with the French. Is it because he's 7 '7"? And French. No way. But his skill set, mostly because he's 7 '7", or he contains that other quality that makes him a great player? So being 7 '7 helps because he's a huge obstacle anytime you're thinking about trying to score. But he also plays like a guard. And there's never really been anybody who moves like him. And it's weird because his whole life has been conditioned to be successful in the NBA from when he was like 12 years old.

56:03Bill Simmons:Is he the new face of the NBA now? I think we're heading that way. If he can stay healthy. But he's learned how to fall because he knew he'd be falling a lot. Oh, learned how to actually fall. How to actually fall where he doesn't get hurt when he falls. He learned English when he was like 12, 13. Like he's been ready for this for 10 years. So I'm a little nervous. You mentioned Southern California in the 70s. I could never tell how much you like California. I loved it then. I came from Indiana and moved out there. And it was troubling to first move to California from Indiana because you'd go days.

56:36Well, here we are in Southern California. You go days without seeing a cloud in the sky. And I thought that was odd. You thought that was bad for you? I don't know if it was bad for me. I just thought it was odd because in Indiana, every two or three days you get a rip roar and thunder and lightning storm and maybe tornadoes and high winds and stuff and hail. And it was great. But in California, it was always that white, hot, silvery sun in the egg, Robin's egg blue sky, like nothing was going to happen. And I can remember one time a surprise thunderstorm blew up in over Mexico somehow, and it rained unexpectedly and nobody had known it was going to happen.

57:15And oh my God, hospitals quit scheduling surgery. They shut down the freeway. Schools were closed. It rained for like eight minutes. And I just thought, I can't be friends with this place. Yeah. We have floods sometimes and the floods come from like an inch and a half of rain. Yeah. And then whenever the freeways get wet, it's holiday on ice. Just look out. So it took me a long time to get used to that. And then I began to love it for every reason everybody loves California.

57:47Bill Simmons:Yeah. You were here initially in the seventies and one of the greatest times. Yeah. That was like the, one of the best times ever to be here. Well, I always like to mention it was so good because Jerry Brown, the governor was dating Linda Ronstadt. Oh, wow. And I just thought, well, this is heaven. Let's, can this go on forever? Yes. Why, why not? One of the first great celebrity couples. And you're in that whole standup scene in the seventies. Oh yeah. The comedy story, it was great. And I think many people identify a creative circumstance period in their life as, oh, it was like Paris before the war.

58:21Well, maybe, maybe not, but it was pretty good. It was a bunch of really funny, funny people. And you would go to work at night and in return for your time on stage, you got to hang around these people and they would make you laugh because not only their material, but they were funny people and they would do funny things and they were unusual folks. Quite a great stimulating peer group.

58:48Bill Simmons:Yeah. So you're doing the standup, but you're also like writing for these sitcoms because we had a million sitcoms back then. Yes, that's right. And that was so good too, because you would say you'd get hired to write a TV show and the pre-production would be like six weeks. And in my case, I got to understand that I was only going to have that gig for six weeks and then I'd get fired. And then they'd get another six week gig and then I'd get fired. And it was delightful because I never had the headache of actually having to work on some show day after day after day, week, month after month. And it would always be new people and new stuff.

59:23And you knew from the beginning that they sucked.

59:26Bill Simmons:Was there a show where you're like, how the hell am I picked to write this show? Why am I on this one? Yeah, most of them. I was hired to write on something called the Paul Linn Comedy Hour. Oh, God. And Paul Linn was tremendously funny. He was an actor. The Hollywood Squares, he was always the center square on Hollywood Squares. Yeah. And really funny and quick-witted, but he was neurotic and I'll just say wacky. uh and the the the paul in comedy hour it was tony randall it was paul in and it was uh gloria uh doris leachman leachman chloris leachman yeah and uh this one sketch that we were rehearsing uh paul lind was the uh was marrying chloris leachman and the minister conducting the ceremony was Tony Randall and Tony Randall was the ex-husband of Cloris Leachman.

1:00:28So there's, there's comedic stuff there.

1:00:32Bill Simmons:That seems like a lot of things happening for that one. It's probably not a wedding. And the big business was Cloris was so upset with somebody that she threw her bridal bouquet and it hit, it hit to him in the right in the face. And it was, oh, Chloris, and he went running out of the rehearsal. It was a high drama. Oh, my God. Yeah, but he was very, very funny. And then you were on the Mary Tyler Moore variety thing, too, I remember. Yeah, that was a good experience because it confirmed everything I knew about myself, which was I have a very low threshold of embarrassment. Very low, yeah. And every Wednesday they would bring in the choreographer, and that threshold would get lower and lower and lower.

1:01:16and there would be professional dancers and it would be the cast of which I was a member. And we had to, I can't even say it. I would watch everybody in the room dance.

1:01:31Bill Simmons:And you would just kind of sort of mimic? That move you just made there, I couldn't even muster that. I would have to be hooked up to a car battery to make that movement. And so we did 10 shows and then I just had to get out. They changed the format. The show was not successful and I just excused myself. There's some things about, like when I think about the stuff I watched growing up, variety shows are one of those that I just can't explain it and it really only worked for the 60s and 70s. And then they would try to keep making work in the 80s, 90s, 2000s. Never worked. But like we watched Donnie Marie.

1:02:08Bill Simmons:That was a really important show. Ben Vereen had one. I watched a lot of those And I don't know if it was just because we didn't have better choices. There's a backbone of network television, that and half hour situation comedies. But boy, you were in for something with those one hour variety shows. Yeah. Flip Wilson had a variety show. That was another one. Dean Martin had a variety show. On and on and on. Now we just have shows where it's three straight hours set in Chicago. And it's like fire, police, hospital. Yeah. You just get to go with the worst parts of jobs in different cities, and that's three hours of your life.

1:02:47Yeah, it's interesting. And back in the day that you're referring to... And you couldn't even pretend the TV would ever go away. No.

1:02:56Bill Simmons:And now here it seems to be teetering. Well, I talk to my kids about this a lot because I'm really fascinated. My generation, we all watched a lot of the same TV shows, a lot of the same sitcoms, a lot of the same movies. We watch you, we watch Saturday Night Live. And then as we got older, we had this foundation of things that we kind of got all the jokes that the other ones would make. And I don't know what that is now if you're 20, because you have like a million kajillion social media people. And I guess there's shows that cut through like Euphoria or Tell Me Lies every once in a while. But for the most part, it seems way more scattered.

1:03:32Bill Simmons:And I don't know if it's good or bad. Yes. I don't know if there's an answer to this. But I rarely watch television anymore. And I don't know why. It wasn't a decision I made. Okay, today is the last day I'm watching TV. I just don't watch it. Do you want to know the show that I do watch and I get a little edgy if I miss it or it's not preempted or something? Is it network or streaming? It's on ESPN and it's pardon the interruption. Oh, wow. Still. I love it. Yeah. Those are my guys. I don't know. I don't know. I find something pleasant and welcoming and they're both avuncular. Tony Kornheiser looks like my new dog.

1:04:15So I have that connection. I don't know. but that's about who is the the kid that was the sports writer at the washington post oh uh thomas boswell yeah were you you predated him or you came after him right i came after him yeah yeah yeah but that book life imitates the world series yeah that was great just great yeah pti

1:04:36Bill Simmons:it's like it's just nice knowing it's there yes you can pop in and out i'll sometimes i'll just watch the first you know first act of it which is like 10 minutes but just seeing those guys and them weighing in on the biggest stories. I talked to Kornheiser a lot and he's just, he's been doing the same thing for 12 years about, I got to get off. Nobody wants to see me anymore. I'm too old. But I feel like he's just going to die on the air during that show. I talked to a friend of mine about what the appeal of that show is. And he just abruptly said, it's the clock. That's it. It's the clock. That's not it, is it?

1:05:16It's those two guys.

1:05:17Bill Simmons:it's the it's this is how we feel about podcasts too it's the chemistry over the idea i think oh with people want to yeah people are there for the for the person every day not the guest not the gimmick i do think though that the show's the perfect amount of time because espn has multiple times tried to extend it to an hour no and tony has always thrown his body into it he's like i'll never do it if it's an hour this is why it's good it's a half hour we leave people wanting more well it may be partly the clock because when you see where they are on that countdown column, uh, you get a little grumpy because, Oh, they're just about to say goodnight.

1:05:55Right.

1:05:56Bill Simmons:The other interesting thing is nobody else has been able to replicate it, come up with their version of it. And people have tried, there's been all these different gimmicks and none of them have worked. It's only been that, but I really think it's, and I was lucky enough to host that show a bunch of times. People are always going to want the two. Absolutely. I figured out how to fit in and what my role was, but those two are always going to be the best. Whenever there's a guest host or somebody filling in for one of the two, it's discouraging. I mean, perhaps that's too strong a word. Right. I'm able to pull myself together.

1:06:28No, I think it's the right word. Yeah. Anyway, that's what I like watching on TV.

1:06:32Bill Simmons:Did you ever think, like Carson used to have guest hosts all the time. You never really dabbled in it that much, right? Oh, no. I was deadly scared that if I gave up the seat, I'd lose the show. Right. You were worried somebody was going to come in and be good. Oh, yeah, because the list of people better, more qualified, funnier, and better looking than me, infinite. And so, no, I wasn't going anywhere. Don't give up the damn chair. I'll wait to talk about watching birds with my son. But in the meantime, don't send anybody in here. Yeah, because Carson would have, at one point, Chevy Chase was rumored to replace him.

1:07:09Bill Simmons:Oh, yeah. You were rumored to replace him. Then it was Joan Rivers, and then she got her on show, and then Leno was the last one. Yep. And then, you know, that was it. Johnny was a man among men, for God's sakes. He knew, just don't, you know, anything you want, give it a try. Let's see how that works. He was so good. And now for a special part of the show called Crunch Time Gifting. It's brought to you by Sephora, where you'll find the best beauty gifts for the mother in your life. You know, I've always got my sports hat on, but seeing as we're gifting Crunch Time for Mother's Day, it's Sunday, by the way, right now I can't help but compare it to the final two minutes of a playoff game how are you going to come up clutch are you going to be like Jalen Brunson I think Jalen Brunson is the score Jalen Brunson in the east Shea in the west the score is I probably trust the most in the last minute of the game you're panicked you're down one who's going to come through I would trust Brunson I would trust Shea so when it comes to last minute Mother's Day gifts only those who turn to Sephora, we'll make the buzzer beater like those guys might be making this round.

1:08:14Bill Simmons:Because a gift from Sephora lets mom know she has loved and celebrated. It's the simplest play there is. And with their Mother's Day gift sets, Sephora has made it easier than ever. Shop Mother's Day gifts at Sephora. This episode is brought to you by Michelob Ultra, the official beer partner of the NBA. With playoffs around the corner, now's a good time to create a tournament of your own. Compete to see who can predict the best playoff series or put your own basketball skills to the test. And the prize? A crisp Michelob Ultra. Plus, they're giving fans a chance to win courtside tickets, prizes, and more.

1:08:48Bill Simmons:Michelob Ultra. Superior is worth playing for. Enter now at Michelobultra.com slash courtside. Michelob Ultra courtside 25-26. No purchase necessary. Open to U.S. Residents 21+. Begins on October 1st of 2025. Ends on June 30th, 2026. Multiple entry periods. See official rules at makelobaltra.com slash courtside for free entry, entry deadlines and prizes and details. This episode is brought to you by PayPal. You know, a clutch move when you see one, a no look past a buzzer beater. Well, imagine if your wallet could pull off moves like that. That's PayPal. Right now you can find offers from hundreds of brands like Sony, Allbirds and Vitor.

1:09:26Bill Simmons:You can save offers for you check out, earn unlimited rewards. Plus you can add those rewards on top of credit card points. Now that is clutch. Download the PayPal app today, save those offers and start scoring rewards. Terms and exclusions apply. See paypal.com slash rewards terms, credit card points subject to issuers, terms, and conditions. What is a late night show in 2026? As both of us are friends with the one and only Jimmy Kimmel. well we have seth myers we have colbert leaving yeah does this can this format exist in 2035 you're asking me an impossible question to respond to i love jimmy kimmel uh it took me a long time to fall in love with that guy because i thought there was something stalking you well it just seemed peculiar he loves you the most it seemed wrong-headed um and and then i love seth myers I think Jimmy Fallon is an outlier because I'm not sure if he knows what decade we're in, but he just comes out and does a show.

1:10:30He can sing. He can dance. He can tell jokes. He is rock solid. Right. But he doesn't quite fit the mold of the other. And then Stephen Colbert, who had the show yanked out from under him. Yeah. I don't know how to answer that because it used to be those shows were so cheap, easy to produce, and long running. I mean, Carson was the proof of that. And everybody tried to mount one like that. But it's like PTI without Carson. It was nearly impossible. I don't know what a new show would look like anymore.

1:11:02Bill Simmons:I felt this way in the 2010s, especially when you were leaving, wondering what era we were going to move into. And what you couldn't really tell at the time was what was going to happen with podcasts. And all these different interviews and the ability of people to respond immediately. And late night shows, taping stuff and being on six hours later. And then people under 35, are they even watching? Like when you had your NBC show, and Jimmy was the same way, I either watched it live or I VHS recorded it and watched it in the morning. Yeah. And I don't know. It seems primitive, doesn't it? All of that.

1:11:40Bill Simmons:It was fun. When you went to LA, that was like that and WrestleMania. I think we're in the same three months. And it was a true highlight. I was like, I feel seen. WrestleMania is now going to be a giant pay-per-view. Letterman's going to be blessed by Carson. Like, this is all happening. Yeah. I was in my basement. But then again, we're dumb if we don't acknowledge that everything changes. True. And knowing that, you can't hang on to things. I'm kind of getting a kick out of I will see a category name the category I don't care what it is of important current celebrities so I'll think alright let me see who these people are number one no I'll just run the list I did not have heard of two dozen people and it's people that are making healthy good happy livings I have no idea who they are yeah it's attention you can get attention without talent well i'm not saying that i'm just saying it's just true i've just turned into the old man who has no idea what these people are doing yeah but i i would say when you had your show talent was usually the great differentiator whether you're a great actor a great musician great comedian whatever now well now you can skip all those steps it seems yeah i'm not sure if you if your position is that in the old days those people were talented well then it's the guy on the lawn telling the kids to go home that's true yeah yeah i'm trying to think you did there there were no influencer type people in the 80s and 90s there were more oddities it was more like whoa what's going on with this person yeah we used to you know subscribe to newspapers from all over the world all over the country in small towns and we would find stories about there was a woman who collected potato chips that looked like famous people.

1:13:38There's a little local story about her. You'd try to get her. There was a guy who collected insects, praying mantis. You'd try to get him. But now that is the lifeblood of the internet.

1:13:52Bill Simmons:You were really good, especially in those first few years of the show of tapping into normal people in a way that, like you had the mailbag. Like you did the Petricks. It was like, oh, these are normal human beings on this show. This is cool. Right. But that was by, uh, that was a bit of a constraint put on us by the tonight show. Yeah. We couldn't duplicate celebrities. Uh, we couldn't have a lengthy monologue. We couldn't have a big orchestra. And, uh, so we, we, a lot of people just put people on TV. And the thing that was always satisfying to me is just regular people who aren't on TV. You put them on TV.

1:14:28They're just fine.

1:14:29Bill Simmons:you know by and large they're just fine yeah it's it's it was interesting as the show when it started to take off you were always so self-deprecating about the show and joking about whether it would be on next week and then people would come on and be like this show's amazing you're my favorite and you would you could always see you'd be like ah so i could only imagine what it's like to do with people like me and kimmel we're telling you like we watch you every night we grew up with you you're the biggest reason I'm doing this? I do. This is what I hear now. It will be a fellow or a woman in a certain age group.

1:15:03And I think, oh, well, because I keep forgetting how old I am. Here's a peer of mine. We have the same influences in life. My great grandfather used to watch you. Oh, Jesus. Oh, ladies. Okay, here we go. But it's very gratifying. I had these two women tell me the same story a year apart about the morning show now nobody watched the morning show on nbc yeah i'm not going to claim i watched it yeah uh and and that's why i was afraid to give up the chair because that thing just came and went you know like a strong wind and the story that i heard from these two women i used to watch your morning show and that snaps your head around because the response is, you're the one.

1:15:48Yes. And it was right after little Jimmy, our first son was born and I would be up early in the morning and I would be feeding little Jimmy and watch your show. I heard the identical story from another woman. And I, for some reason, those elements, it was a very pleasant reminder of, it's not really all about me. It's supposed to be something for others. And in these two cases, it had been. And I thought that was very sweet.

1:16:19Bill Simmons:So, I mean, that was your big quote unquote failure, the morning show, but it turned out to be the best thing that ever happened to you. Yeah. And the worst year of my life being out of work, it was just horrifying. How long were you out of work? I think it was a full year before I went back at 1230. And what were you doing? Just stand up and pitching stuff? Not even, I was doing, you know, looking, sniffing around at what would be failed projects, but mostly I was drinking and, and drinking to excess. And, uh, it was, it was a dark year. Are you in LA or New York? It was in LA. Yeah. Uh, and I describe it as a dark year.

1:16:56I know of people who actually have had dark years. So forgive me. I'm not pretending that being an out of work comic really rates as a dark year. But for me, you know, my own little self-centered world, yeah, things weren't going the way I wanted them to go.

1:17:12Bill Simmons:Yeah. Sometimes I feel this way about me with a couple of things, like failing turned out to be the best thing that could have happened, but I didn't see it as it was happening. Right. You don't realize till after like, you know what, that was actually pretty good. Cause that led me to this, this, this, and this. And yeah, I always tell people, when people ask me for advice, I always say like, just keep taking chances. And sometimes it's okay. If it doesn't work out. Just move on to the next thing. I never know what to say when people say, can you give me some advice? I don't know. I don't know what to say because it was so easy for me in the beginning.

1:17:43Yeah. I just had a plan. I saw it. It was all there. The blueprint was obvious and I followed the blueprint perfectly and it worked for me. So I don't know what to tell people. I wouldn't even know what you do. I know people that I just think are people. And then they say, well, yeah, you can contact me on my socials and then they give you whatever address you need. And they've got like 2 billion followers. And I do, I don't, how did that happen? How does that happen? You're one of those guys, right?

1:18:13Bill Simmons:Yeah, I don't have that many, but it's, you know, I came in with some of the social media stuff right at the right time when you could build audiences. Now it's like the TikTok. I don't do TikTok at all. I don't really understand it. I mean, I understand it. I don't understand it for me. Like I'm in my mid-50s. I want you to help me out with something. Yeah. And going back to our discussion of ideas. Yeah. I went to Finland and watched hockey games. I went to hockey games in Finland. What kind of hockey games? Professional hockey in Finland. Yeah, one in Helsinki and then another in a Tempere.

1:18:54I think that's the name of the town. It was great, by the way. It was delightful. And then some of the kids on those teams showed up for the Finnish Olympic team. but I watched tie games, saw two tie games and then the shootout. So here's now what I want you to help me with. Yeah. The NFL, and I know that like Chris Russo hates the fact that there are guys kicking six yard field goals now and he thinks that that should be banned. That should be limited. Get rid of it. It's not football. If a football game, pick two teams. Yeah. Patriots and Jets. Okay. At the end of regulation, the score is 7-7.

1:19:36What do we do? Okay, we have another full overtime period, okay? If at the end of the overtime period the score is still tied, then what do we do?

1:19:45Bill Simmons:Well, in the playoffs, it just keeps going forever. No, no, no. We have a kickout. Oh, that's what you want to add a kickout. Yeah, we start the kicker at the 50. He makes it. Then the other kicker, opposing team, has to duplicate that. If they both score, go to the 55-yard line. and if that works, you go to the 60, and the first one that can't convert a kick from that, then the game is over. What's wrong with that? It's pretty good. Now, you've heard this before, haven't you? I can't be the first one to think of this. No, I've heard variations of it, but then other people would say, why would a kicker determine a win or a loss?

1:20:23Bill Simmons:Some people hate that. I have people in my life who feel like we should just get rid of extra points and field goals completely and just have touchdowns. touchdowns and two-point conversions well i what's wrong with just a bit of variety in the goddamn game yeah you know i the regular season now it work the kid the kid for dallas the guy who kicks routinely 60 plus brandon aubrey yeah yeah well that's that's tremendous to see yeah what a great physical accomplishment that is nobody understands seems to understand why kicking has gotten so much better. Secretariat is still faster than horses we have now.

1:21:01Bill Simmons:Pitchers can throw four or five more miles an hour than they used to. Well, Bob Feller comes to mind. Right. Well, but I'm saying like the radar gun was usually 96, 97, 98. Now there's guys throwing like 104. And then the three point shooting being so much better. But yet like the marathon, I always talk about this with Malcolm Gladwell. We were always wondering when somebody would go under two hours and it actually just happened in London. They did one hour of 59 something, but it's like, how is there a point where you can't just run faster in a marathon? Like you just hit a wall basically. Perhaps, but going back to kicking, let's just see how far a guy can kick.

1:21:41Can he kick a hundred yard field? So you love field goal kicking. This is one of my big revelations. And the fact that it ought to be determined by moving the football on the ground. if you can't determine the outcome of the game in five quarters by moving the ball on the ground, passing and running, okay, you're paying the price for that. We're turning it over to the kicker. And it's football for the love of crap. You know what? Why do we resist that? And here's the other thing. And you can do something about this because I know you know people. I'm a powerful man. Yeah. The quarterback ought to punt.

1:22:18Bill Simmons:They used to have this. Thank you. Thank you very much. Yeah. He's another one. But that used to be part and parcel of the gig. So punters are out. We've just cost 30 punter jobs. No, I don't want to get in trouble by saying punters would be let go. No, keep the punters. We'll have punters and they can do stuff. They'll do other stuff. They'll do other stuff. What do you think of the theory that we should get rid of, either they should get rid of three-pointers completely in basketball or there should be a cap on how many you can make in a game. Okay, here we go. You hit 15 and you're done. Here we go.

1:22:50The thing that I'm having trouble with is the three-point line isn't consistently the same distance.

1:22:56Bill Simmons:What do you mean? Down toward the end of the court. Right, and then it goes up. Yeah. So you get a shorter three-pointer down in the corners, correct? Yeah. Then you do at the top of the arc. Right, so extend the court. I don't know, but you're never going to get rid of the three-point. Can you imagine just going back to watching guys do layups and soft jump shots? No, we need the three-pointer. I wouldn't mind a cap, though. I wouldn't mind being like, you can only make 20 in a game, and that's, once you get to 20, you just, it's removed. Here's what I want to do, is you, 10 foot, the basket, the rim is 10 feet.

1:23:30Bill Simmons:Yeah. The first quarter, it's 10 feet. Second quarter, it's 12 feet. It just keeps, just moves around. So in the fourth quarter, what is that? 16 feet. Let's just do that. One of the theories is that every team should— No, I don't think you're taking that seriously because you quickly changed this. What do you mean thinking it'd be hard? They have to stop the game to raise the baskets. The thing is in a hydraulic deal and it's just okay. The fans, here it comes. And maybe some lucky ticket holder gets to press the button. It goes up to 12 feet. One of the ideas that people do like is that every team can determine where the three-point line is.

1:24:07Bill Simmons:So you could build a team— Oh, so it's like a baseball field in your hometown. Yes. You could build a team and like, you know what? We're going big guys. We're going bigger. And you make the three-point line. It's like basically 30 feet because you're not going to shoot them. Yeah. And you dare people to do them. Baseball, I have a lot of faith. I've always had this thing where I called myself to sports art, give me the job. I would do all these things. Baseball pitch clock is the single most successful new idea I think anyone's come up with. But they're slowing it down, slowing the game down now with the automatic ball and strike counter.

1:24:41Oh, you don't like that? Well, I haven't actually seen it. But doesn't that then slow the game down? It's quick.

1:24:46Bill Simmons:They just do this, and it's like 10 seconds. What it's done is they do this on their helmets. I know. They hit the helmet, and then that solves everything. Well, what's happened is they've completely undermined the confidence of the umpires. Because what we're realizing is the umpires are all terrible. These guys got a union of their own. They got to be raised in hell. They're like, what the F? Yeah. How did we end up with this? Who was the umpire retired a couple of seasons ago who was known up and down throughout the league as being God-awful? Pick one. Yeah. Yeah, there's a couple of them. And they just said, well, here he is again, and there would be highlights of him blowing calls.

1:25:19But in terms of baseball, there is an advantage if you're a left fielder, a left-field hitter. Left-handed hitter, yeah. You get a jump. You get a step down to first. If you're right-handed, you've got to cross the plate and get down to first. True. So it should be, both of you got to cross the plate. If you're a left-handed batter, you got to run. You run the bases the other way? No, you got to run to third. Interesting. If you're a right-hander, you can run to first. That would be a controversial change. And then here's where the fun gets really fun. They meet on second. What do you do then?

1:25:53They cross paths. Well, you'll figure it out.

1:25:56Bill Simmons:Yeah, all right. I'll work on that one. What would you change about golf? What's to change? Yeah, you like golf, right? Or you like watching? I enjoy watching golf. I'm so pleased that the Live Golf Tournament seems to be having financial troubles. Oh, yeah. Because in the beginning, yeah, and you can wear shorts and we'll give you a billion dollars. Shorts, yeah. And now, all of a sudden, they're looking for other ways to finance it. That one's done. I did get a kick out of the Masters, Rory McIlroy or whoever that was. that was tremendous you room for him well how could you not trying to win two in a row that was pretty cool yeah i like him because i got this great mailbag email thank you for the mailbag idea by the way it's stole that from the moment i started writing a column but i got a great mailbag idea somebody who was a celtics fan and a rory mcelroy fan who lived in ireland it was basically saying it's the same experience rooting for both where it's like a lot of talent but i always feel like they're going to fall apart at any time celtics you miss threes worry like we'll self-combust and it's like did i is this just an accident or is this what i'm attracted to as a sports fan yeah but very similar yeah and then and then the masters and we call them patrons have you been you would love it they take your phone it's like going back to 1920s you have to like interact with people appeals to me perhaps this is the single feature that appeals to me about the masters is the pimento cheese sandwich unbelievable because we used to I don't think they even make that anymore.

1:27:33They have to make it at the course. It's not legal to actually prepare that.

1:27:37Bill Simmons:Is it pimento cheese? They have pimento cheese sandwiches, but then the hack is you also buy the barbecue chicken sandwich and you mix them. My buddy Joe House, I think, invented that. How drunk do you have to be to do that? At least a couple drinks in. Yeah. And the sandwiches are like$1.50. Nobody has phones. People just walk around. If you and I get split up, I might not see you again for four hours. There's just no way for me to know where you are. We're just gone. And then you compare that to the Waste Management Open in Phoenix. Well, yeah, that's a social outing. I mean, that's a prison break, isn't it?

1:28:12Yeah.

1:28:13Bill Simmons:They just want everybody to be super drunk there. Yeah. And that's okay with the golfs? I think they kind of lean into it. I'm interested to see what they do with the new commissioner because I think he wants to move more events to the West Coast, have it be prime time on the East Coast, stuff like that, like to try to speed it up. I like when people come into leagues and want to change stuff. Yeah, I don't have a problem with that. But in golf, you know the big tracer mark they have? You'll hit a tee shot and then they show you the tracer. You like that? Where they show you where it went? Yeah, and how high and how fast.

1:28:45If they could generate that so it happens in real life, not just on TV, oh boy. You'd have to beat people away with a stick. They'd be when the gate's open.

1:28:59Bill Simmons:That would be a really good. Oh man, what a visual. It'd be like fireworks. Did you get an F1 or are you just your old school? No, I used to love Formula One back in the era of Ayrton Senna and Nigel Mansell and those guys. And went to a lot of Formula One races and just, just really loved it. And I think in those days for me to really love it, it was because of like we're talking, it's the personalities more than the content. Yeah. And, uh, I just, something about Ayrton Senna and Nigel Mansell and they were, uh, enemies on, on the track and the personalities and the characteristics. And I don't know, I did love it.

1:29:42And now it's IndyCar, I'm part of an IndyCar team. And it's, uh, I enjoy that. I love that.

1:29:48Bill Simmons:Did you ever think about buying a minority stake in a sports franchise? No. Never? No. Just buy a little piece, a little taste? I think for a while I was part owner. I had some stock in the Seattle Mariners. Really? Yeah. When was that? Jesus, it would have been in the 80s, mid to late 80s. Wow. Jeff Smullyan, for a time being, the guy who owned Emma's radio, sports radio and beyond, I think had purchased the Seattle Mariners. And I was a stockholder or board of directors or something. You did like, I think over 6 ,000 shows on NBC and CBS. Were athletes ever really good guests? Or were they, or was it you were the one that had to do all the work?

1:30:37Bill Simmons:Can you remember guys coming in and actually being good other than like Charles Barkley? That's something to reflect on. I think they were pretty good because I always knew exactly what I was going to talk about. Right. Because this was in the, the, the, the ending day when sports illustrated was a thing. Yeah. And, and it, it helped me live my early life getting the weekly sports illustrated magazine. So I had that kind of interest built up from looking at the voluminous detail and data and personality. So I would attribute, I would use that to talk to sports figures. So they were always pretty good.

1:31:17Bill Simmons:Cause I remember Michael Jordan, the first time he came out. Jordan. He was great. You could tell he had it. No, he, yeah, you could tell he had it, but he did, he had a disliking for me. Oh really? Yeah. He was on once and he was on to promote his, the new Air Jordans. Yeah. The Air Jordan. I just saw that movie not so long ago, Air. I liked it. Tremendous. Yeah. I really liked it. Oh, it's so good. Yeah. Very good. Uh, yeah. So, uh, yeah, but we couldn't get him back. He would never come back. Really? Yep. And I finally called him because I kept imagining and perhaps not imagining, perhaps really that I had offended the guy.

1:31:56And I didn't, certainly didn't want that to have happened. And I called him and I flat out asked him, I said, we really would like you to come back. Is there a problem? And he said, no, not a problem. But he never came back. Interesting. Yeah. A real disappointment. Yeah.

1:32:11Bill Simmons:Cause you had in the eighties that your show was how I found out about a bunch of people like Seinfeld, he came on your show. That's how I knew who he was, you know? And that was why when he got the NBC show, I was like, oh no, this is going to be good. He used to kill it on Dave's. Yeah, that's right. There was a bunch of those from that era. I get very little credit for the success of Seinfeld. You should get a percentage. I was right there. You were right there. I was like, what's his name? Kramer. I could have been the, could have been a Kramer. I saw him do standup twice in the eighties. I made my parents take me just because of the Letterman appearances.

1:32:45Bill Simmons:Really? Oh yeah. I thought he was one. I thought your best guest during that stretch, like the ones I was, Leno was the best one. I mean, that was like every three, four weeks, but he would come in and just kill it. Jay was so good. Yeah, and you were so delighted. You guys were just great together. So he was one. Seinfeld, I just thought Michael Keaton was great. Oh, I love Michael Keaton. He would come on and just crush. But see, those guys, now Jerry was a class or two behind me. But me and Leno and Michael Keaton, we were all there in the same room at the same time. So I always got a big kick out of, we each knew something about one another that we weren't going to share.

1:33:29It was great. Well, and you had George Miller too a bunch back then. Oh, my good friend George Miller. Oh my God. What a fascinating, interesting fellow. Just tremendous. this.

1:33:41Bill Simmons:Yeah. So it went all the way through to when you were still doing the show. And then it seemed like Norm became your favorite. Norm became your new favorite one. Well, that was the connection. George Miller was the connection to Norm. Yeah. When I found out Norm liked George Miller, then I fell in love with Norm. We've never, Norm is one of those guys. I think social media has weirdly really helped him because he was always really funny. He had a good career, but now like the snippets of him, there's nobody like him. He's like growing in esteem now. That's right. You can't, get enough of those things.

1:34:11Bill Simmons:He was like an all-time one-on-one. And everything he does is still as funny as it was. Yep. Yep. And a guy who kind of reveled in dead silence after a joke. Just like, that wasn't his problem. That's your problem. He loved it when the audience was uncomfortable. Yeah. Yeah. I feel this way when I read stuff I wrote, and I don't remember that I wrote it. I'll see some... I'm like, I think I wrote about this, and I'll find some column in 2004, and I'm like, I honestly don't even remember writing this. I'm reading it like I'm the reader, like I didn't write it. Do you feel that way when you look back at 6 ,000 shows?

1:34:47Bill Simmons:I don't remember. They just blend in together? I don't remember. I don't remember how I got here. But I want to tell you one George Miller story, which I absolutely love. He had a girlfriend, and they were together for years. And it was always George and her girlfriend. His girlfriend, her name was? MJ. That's right. MJ. Initials for other names. But they were close. And then she decided she had had enough of George. And so she said, George, that's it. You're done. So George, because he was George, broke into her house when she was out. She started dating an architect. And this drove George nuts because he wasn't an architect.

1:35:33He wasn't, you know, he was in the sweatshirt and the pants and his tennis shoes. And he was telling jokes. So he breaks into the house and, uh, she realizes that it's been broken into by George. So she calls the police, the police go to George's house and they say, uh, do you know, and George is playing dumb. No, no, that wasn't me. What, what happened over there? Well, nothing was stolen, but the thing was damaged and poked around and there was a picture she had of Jesus Christ that had an obscenity written across the face of Jesus Christ. And George says, Jesus Christ, I thought that was Dan Fogelberg.

1:36:18And I just, I mean, how can you, isn't that, and here's how delightful that is. At his memorial, his girlfriend told that story. I mean, that's otherworldly. I thought it was Dan Vogelberg.

1:36:33Bill Simmons:So who, who was he in your top five people who hit your funny bone the hardest? He, he became a good friend. He was in that, the same class with, with me and, and Leno and Michael Keaton and, Robin Williams came in a little bit later, but still in that class. Yeah, he counts. Uh, and, uh, yeah, he was just such a strange character. He, uh, I never met anybody quite like him. Does Kaufman count that? or is he a little earlier? Kaufman was so, no, I think he'd gotten a head start and was way ahead of us at the time. But he was, you didn't buddy up with Andy. Right. You, you, you know, stood aside when Andy came through.

1:37:13So you would see he was on the show and you'd be like, okay, buckle up. He was great for the show. Yeah. Because it was just, you knew, but you didn't know the dimensions of what you knew. You know, you had the idea, but you knew it wasn't going to be this big. You know it was going to be that big. Right. And you just sat back there and were entertained by it.

1:37:32Bill Simmons:So who hit your funny bone the hardest out of anybody? Well, Jay made me laugh really, really hard. Because he would come in and he'd come at you. It was like he was like the road team and he would try to turn it on you every time. Yeah, but he was, when we were working at the comedy store, he was the funniest in the group. You know, he would go on. You couldn't follow him. He was so funny. Right. Yeah, you know, I know you hate talking about this, but I used to love Leno. And then when all this stuff happened with you and he got the Tonight Show, I really felt betrayed. It was like I was learning the lessons of business friendships versus actual friendships.

1:38:08Bill Simmons:Because my attitude was like, I would just never do that. Letterman was my friend. He's the whole reason I have a career. I would never want to go head to head. But then you get older and you learn in life. A lot of people are going to do what's best for them when they have the chance. Sure. I wish I could say he was a dangerous criminal. He's not. Right. And that's what happened, and that's what happened. Did you ever see the movie? No. I think I asked you this. No, I never. I can't imagine anything you would hate more than the Late Shift movie and somebody playing you. I couldn't watch my own show.

1:38:40I'm not about to watch a movie about my own show.

1:38:44Bill Simmons:That would be a fun, if you ever got into social media, the social media should just be you on camera watching the Late Shift. With a steady camera on you as you start convulsing. I think that I, maybe I mentioned this to you, but they, um, at some point, uh, a friend of mine who worked with us on the show named Stuart Smiley, Stuart Smiley, is that who it was? Stu Smiley. Yeah. Had given me, um, some kind of trampoline thing where you would pitch a ball into and it would return. Bounce back. Yeah. Yeah. And they depicted me at my home on the weekend throwing, I don't know, something toward this thing and it bouncing back.

1:39:35And it was complete fabrication. I don't think I have it right. I don't think I was ever even gifted at this thing.

1:39:42Bill Simmons:Yeah, I know the scene you're talking about. It's actually a really good movie, but like always with these things, it's based on a true story. And once you say based on a true story, you can basically do anything. Yeah. You could just have you, you know, hitting three woods in your backyard. Well, that would have been preferable. This was something a dope would be doing. Here I am depicted as a man in his 40s bouncing the, I don't know what it was, but it was humiliating, I tell you. What has drawn you to this Netflix show? This episode is brought to you by Sephora. You know, moms, obviously the best, whether you have a mom or you're married to a mom or you have both, they definitely deserve the best when it comes to Mother's Day gifts.

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1:41:33Bill Simmons:Hire right the first time. Get started by posting your first job for free at linkedin.com slash Simmons. That's linkedin.com slash Simmons. Terms and conditions apply. and what makes you want to keep doing it? What's your favorite thing about it? Oh, it's been nothing but fun because the schedule is just about right going back to retirement. It's enough work to keep you juiced. And if you don't have that, then you get sad. Right. So we've done enough of those to be... And then here lately, we've done a string of stuff that's been pretty fun. And you get to travel, you get to see people and you get to run into people that tell you about when their grandfather used to watch in the hospital when he was dying.

1:42:13And they were all there around him and they were watching the top 10. His last wish was to watch your top 10 list before he died. So yeah, the people at Netflix, and I would love to just go nuts and tell you how awful I think they are. Because I have that gene. Just pick a place where I worked and I hate them. But I can't do that with Netflix. We started, I don't know, years ago, four years ago. I don't know when we started. but they've been nice. They've been friendly. They're pleasant. They invited me to their barbecue on Thursday. Right. Yeah. So it's been a great experience. And like I said, the schedule has been enough to satisfy me being out of work.

1:42:53Bill Simmons:I feel like I learned that from you, the always turning it on your boss, the person who's employed. It's so easy. It's so easy. Well, I ended up getting suspended and I had to leave. Oh, you got suspended. Yeah, I got suspended for three weeks. Well, what were you doing? I was very critical of Roger Goodell and knowing that he was their biggest partner and, you know, in retrospect, probably pushed a little too far. Oh, that blows. That's not right. Because they're the punching bag in the gym and you don't take the punching bag out of the gym. That's why they're there. There's nothing you can do to personally affect the bottom line or the stock price.

1:43:34Bill Simmons:Well, then they realized, like, by the way, there's nothing you can do to affect the bottom. You're going to leave now. And we'll be exactly the same, which is what you learned. I'm telling you, this is exactly what's wrong with this country. Is it really? I don't know. Maybe. Well, the thing, when I started writing my column, and they had all these media criticism rules, so I had to figure out all these different ways to, like, make fun of announcers and Chris Berman and, you know, do these roundabout things. And it actually kind of was fun creatively. Yeah. How do I get the message across without hitting somebody up the head with a hammer?

1:44:08Bill Simmons:You know, which I think Howard Stern was probably like that a little bit, too, when he was on the radio versus being on satellite. You're on satellite. You can just say anything. But you mentioned the NFL has a large share of ESPN. Is that correct? No. Well, the ESPN, their most important TV partner was the NFL. Right. So they didn't really want people to be that critical in the NFL. And at the time, there was a lot of things to be critical about. But I understand recently that there was a great— They bought a steak, yeah. So is that okay? That the single biggest topic of the sports broadcasting owns that outlet?

1:44:44It seems a little dubious. Yeah.

1:44:46Bill Simmons:Yeah, it's—they own a piece. They run the NFL network. I mean, they would say, and I would agree with them, that they're still doing investigative journalism. They'll still write about the league. They try to be objective. But you always have that air of like, ah, is this objective? So you just got to prove that it's objective. Yeah. And what is the line before you get the phone call? You know? Right. That was my issue when that, when I had all this stuff with Goodell in 2014, cause it was all about that Ray Rice story that had happened. And I, you know, we did good ESPN did good reporting on it and I was expounding on the reporting.

1:45:21Bill Simmons:I felt like he changed his story and probably went too far. You probably, I'm trying to think when you went too far, probably, probably late eighties. You started pushing it with NBC a little too much? The only real trouble I got in was making a joke about Sarah Palin. Oh, at CBS. Yeah, and then I remember one time, what's his name from CBS? Les Moonves. Yeah. He said, he called me. He was in town for the upfront through some nonsense. I don't know. Yeah, I'd like to come over and have a chat with you, Dave. And I said, oh, okay. That sounds terrible. Yeah, so he comes over, and I always try to make them uncomfortable somehow.

1:46:05So I would sit where you're sitting, and then they would have to sit behind my desk. So I knew that that was a bit of a head fuck, you know, like, wait, why am I sitting behind his desk? And he looks at me, and it was like being back in high school. He said, what is your problem with me? So I loved that moment. Why did he think you had a problem? Because you were making fun of CBS. I was working him over on the air. And then, of course, because I'm just, I guess, a classic.

1:46:37Bill Simmons:That was your show for 30 years, though. I know, I know. You would always make fun of whoever it was. But I folded right up and I said, oh, geez, nothing. It's all fine. We're just having fun here. We're just a bunch of kids. And it was like that. Whereas I could have just gone after him, but I didn't. Well, if people didn't play along with the joke with you, it would make me, the viewer, not like them. Yeah. Because I remember you did the book. He did the bullhorn thing with Brian Gumbel when he was doing the Today Show, and he didn't react great to it. I was like, that guy's a fucking asshole.

1:47:04Bill Simmons:Like, why doesn't he get that this is a show? Yes. Brian Gumbel was a thousand percent right to be upset. Yeah. Because they're doing a primetime live Today Show, and I'm leaning out the window with a bullhorn. And then conversely, like on the opposite side, like when Vince was on your anniversary, Vince McMahon was on the anniversary show kind of having fun. and was like, oh, Vince McMahon. Didn't realize he had a sense of humor. Like, you know, it could definitely sway how you felt about people. Costas was another one. Costas was always great. Well, Costas was, I mean, he was on the payroll in the beginning.

1:47:39He wouldn't do anything, and he was great because he had the right sensibility, and sure, I'll play along, and it's not going to lean on my integrity as a sports broadcaster. He was great.

1:47:49Bill Simmons:Yeah, Kimmel and I have talked about that. You felt like, especially for us, like growing up, like idolizing the show, everybody who played along or, or could fit in. We just liked them. We were like, okay, they're in the club. Let's bring them in. It was like the Soho house. Wow. You're, uh, explaining power. I didn't realize I had you, you had it now, you know, you know, you have it. You just pretend. No, no, I know. Because in those days, I don't know how you feel about this, what you're doing right here. I didn't realize was not aware. didn't have time to consider that what we were doing in that studio was anything beyond the 300 people in the audience.

1:48:27If you've been doing it every day, you're doing it every day. And if it's like running a restaurant, if people are sending the soup back, you realize, oh, we got bad soup. Right. And I think for a while we were the only TV show that served soup.

1:48:40Bill Simmons:Well, I remember, I think you were on the cover of Rolling Stone at some point and that felt validating because it still mattered to be in the cover. SI and Rolling Stone, if you made the cover, like something was happening. So that was that you probably knew at that point. I, uh, I only knew of the Rolling Stone importance because of the song on the cover of the Rolling Stone. And I realized then, oh shit, maybe this is something I would like to be on. And so I finally ended up on the cover of the Rolling Stone and, and that was cool. I loved everything about it, but the photo shoot, you know?

1:49:14It was always something wacky. Can we do something wacky? Yeah. And that always made my skin grow.

1:49:21Bill Simmons:They taught Kimmel. Kimmel had an ass crack shot. They did it for an hour and then he did like a fake plumber thing. And of course that was the one they used. Yeah. Yeah. They just, they try to let your defenses down until you do something dumb. And then that's the one they use. You just, you can't trust those people. So what's, what's next for you? More Netflix shows? Well, no, when I leave here, I'm going to have lunch with a friend at a deli. That's what's next. What about rest of the year next? Any chance we see you courtside for a Knicks playoffs game or anything? You're never doing that stuff.

1:49:54Bill Simmons:Let me tell you something. It's like we're connected psychically here. Saturday, I will be in Indianapolis at the Herald Square Arena, whatever they're calling it now. Oh, for the Caitlin Clark? Yeah, season opener for the Fever. Tommy must have helped you. Dallas Wings. I think I did this on my own. Did I do it on my own or? You did it on your own? I didn't. You didn't need Tommy? I think Mary did this. Wow. Did he do it? Oh, he did it. I'm sorry. Oh, you did it. You know, Tom is like the string puller of the fever. I don't know. I just don't know about Tommy. Still figuring it out. Oh, well, I don't know.

1:50:34He's a member. Did you ever see the Woody Allen movie Zellig? Yeah, that's Tommy. I'm being told now. Yeah. It was a Brian Teta connection. And anyway, I'll be there. Speaking of courtside, not courtside. They tell me they can't put me at courtside, which is fine. Huh? Might it change? I'll be at courtside. This is breaking news for you, Bill. Wow. I'll be courtside. This is great. I just say a few things about Caitlin Clark. Uh, I got to know her a bit. Yeah. Uh, the same way you can tell people that you know me and nothing beyond that please.

1:51:13Bill Simmons:I just say a bit if they ask. I know Dave a bit. And I just fell in love with her because as a person, it's, that would be like the daughter who comes home for Thanksgiving dinner from college and you just, the house would light up when she pulled in the drive and was home for two or three days. I had that feeling about the kid. Oh, that's nice. And, uh, and so we did this show with her on netflix and uh about a month afterward i thought let me let me call caitlin because i feel like i put in my time right i can get a call and then it was all of a sudden well what do you want to talk about well i just want to see if she was happy with the show yeah okay well let me see what we can do i don't know that was two years ago never wow never got to call It's a lot of, what is that?

1:52:05A lot of people. Is it me? Is it just don't do whatever you do?

1:52:09Bill Simmons:Don't let asshole call. No, that I don't think it was. She probably didn't even know you called would be my guess. Your mistake was not going through Tommy. Tommy, didn't we go through you? No. See, Tommy never happens. Well, who the hell did we go through that? How often? Let's try and get her on the phone now. How often do you go back to Indianapolis? Well, I go back every year for racing activities. and then I go back to visit my family here and there, which is the family's getting smaller and smaller. You know, death. Yeah. Yeah. And I like going back. Indianapolis has turned into a tremendous place.

1:52:46It's a great place to live. You got to overlook a few things. You have to overlook a few things. Yeah. You have to overlook some things. A couple things. But it's still a great place.

1:52:58Bill Simmons:I went back for the finals for two of the home games for Pacers OKC. Oh, yeah. I spent like five days. Yeah. I mean, it's perfect. It's a perfect like come in and out for four days. Didn't we know that that was not going to last? I mean, Therese Halliburton and then all of a sudden. Yeah, but here's the thing. So we're taping this before the lottery on Sunday and they have a really good chance to get a top four pick. And the draft's awesome. Therese is coming back. They traded for a center. So I think they're going to be really good next year. Well, that'll be delightful. I go back to the ABA days and it was just, I loved it.

1:53:34Bill Simmons:Oh, that's right. You were there for the old Pacers. Yeah. Yeah. It was delightful. Who else was on that team? Billy Keller. Freddie Lewis, Billy Keller, Mel Daniels, Roger Brown. Mel Daniels was a... Rick Mount played. They won the title. They won, I think they won three ABA titles. Yeah. Yeah. And it was delightful. It was in the old Indiana Fairgrounds Coliseum. And tickets were 75 cents. And you'd go and it would be like an old black and white movie about fighting. You could just see the haze settling over the ring. Right. And the only way you knew there was because of the colored ball. Oh, I see them.

1:54:15They're down there playing basketball.

1:54:16Bill Simmons:It's so funny that there's barely any footage of any of the games. It was just this alternate league happening. Well, there's a tremendous documentary that I just watched. It was on Amazon, yeah. Yeah, yeah, yeah. Pretty good. Pretty good stuff. Yeah, I hope, hopefully Indianapolis will come back. So you won't go to a Knicks game? No, I would. You could be on Celebrity Row with Chalamet, Larry David. You could be right there with those guys. Good for them. Dear people. I'm afraid that I would probably get beaten. I don't know why. I just have that fear wherever I go. But I mean, when you're in New York, you're like New York royalty, though.

1:54:54Bill Simmons:Aren't you? Really? I think so. I mean, you did a show there for 33 years. And that's what it takes to become royalty. Yeah, I would say. Well, people have been very, very nice to me. And Colbert will go through this. Yeah. It is now, oh, we miss you. And you'll get to the point where I know if you really miss me, I'd still have a show. You understand? You see what I'm saying? like that. All right. This is a true pleasure. Now don't tell me we're finished because I'm just kind of settling in. Tom's ready to go. Tom's been running. Yeah, this is, Oh yeah. I'll be at the deli. Yeah. You got to go to the deli.

1:55:36The hair to your Ruben. Yeah. Comedy. Your Ruben. Well, this has been a great pleasure. And I feel like I would like to come back and do a better job.

1:55:45Bill Simmons:I thought you were great. I had a great time. I'll tell you what happened. Uh, last night, uh, I feel like I was dragged out of a bar unbeaten because it was John Mulaney. Yeah. And it was a big, big, big deal. Yeah. And so, of course, I didn't sleep. And now today you're getting me at like 60%. Getting groggy Letterman? Yeah. I thought you did great. Thanks for coming on. Well, what are you going to say, for God's sake? The producer's not here. I had a phenomenal time. I wish in retrospect I would have invited the producer. sir. Well, now you're going to look into this guy. I'm going to look into this guy for you.

1:56:22Bill Simmons:Thanks for coming on. I appreciate it. Thank you, Bill. I enjoyed myself as much as I'm able. Thank you for the, for the viewer meal idea for the mail. Anything you got. It's all yours. I got 18 years out of mail bags and now more on the podcast. So thank you. Thank you. All right. That's it for the podcast. Thanks to the one and only David Letterman. Thanks to Gahau and Eduardo as well. Don't forget to watch Tropic Thunder this weekend because that's the next rewatchables on Monday. So here's the schedule for this weekend. Sunday night, there's two games, New York, Philly, the lottery, and then San Antonio, Minnesota, which should end around 10 o 'clock ET.

1:56:58Bill Simmons:I'm coming on live on Netflix with a couple of guests, and we're going to break down the lottery and all the basketball for the weekend. So enjoy the weekend. I will see you on Sunday night.

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