Best of Monday 2025

22 Dec 2025 · 1 h 18 min

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Podcast Episode Summary: Armchair Expert with Dax Shepard - Best of Monday 2025

Episode Overview In this special episode, Dax Shepard revisits some favorite moments from the Monday episodes aired in 2025, featuring guests including Nikki Glaser, Brad Pitt, Dove Cameron, Adam Scott, Mindy Kaling, and Charlie Sheen. The discussions highlight personal vulnerabilities, the nuances of celebrity life, and the impact of family dynamics, woven through a lens of humor and candid storytelling.

Key Guests and Highlights

Nikki Glaser (Episode 861)

  • Grammys Experience: Shares feelings of inadequacy despite being nominated and the pressure of celebrity interactions.
  • Depression Post-Award Shows: Discusses the emotional comedown after being surrounded by famous figures and the realization of their humanity.

Brad Pitt (Episode 911)

  • Career Decisions: Talks about leaving college just before graduation to pursue acting.
  • Humorous Audition Stories: Shares a humorous experience attempting to get his SAG card while working as an extra.

Dove Cameron (Episode 879)

  • Relationship with Dad: Reflects on the complexities of trying to mend a relationship with her father amidst feelings of depression.
  • Navigating Family Dynamics: Explores the emotional impact of her father's struggles and their effects on her mental health.

Adam Scott (Episode 846)

  • Grief and Filming: Discusses the intertwined nature of his personal grief and creative work while filming "Severance."
  • Struggle with Expectations: Talks about the pressure of performing and managing personal loss.

Mindy Kaling (Episode 864)

  • Ambition and Sexuality: Shares insights on writing about ambitious women and the portrayal of female sexuality in her shows.
  • Cultural Reflections: Discusses her experiences as an Indian woman navigating dating norms.

Charlie Sheen (Episode 954)

  • Humorous Anecdote: Recalls an incident where he fell asleep on camera and humorously relates it to personal challenges.
  • Father-Son Dynamics: Touches on the influence of his father and the expectations that come with that relationship.

Themes and Discussions

Vulnerability in Celebrity Life

  • Many guests share their experiences of feeling overwhelmed by the expectations of fame and the impact it has on their mental health and personal relationships.
  • The episode emphasizes the messiness of being human, showcasing how even successful individuals face struggles and insecurities.

Family Impact

  • Discussions around family dynamics highlight the lasting effects of parental relationships on mental health.
  • Guests like Dove Cameron and Adam Scott discuss how their familial relationships shape their identities and emotional landscapes.

Humor as a Coping Mechanism

  • Humor pervades the discussions, with guests sharing funny anecdotes that serve as a way to cope with their experiences and challenges.
  • Dax Shepard’s approach often blends lightheartedness with deeper human truths, making complex emotions more relatable.

Key Takeaways

  • Self-Acceptance: The importance of recognizing one’s vulnerabilities and embracing them as part of the human experience.
  • Connection: Building connections with family and friends is crucial, even amidst struggles and misunderstandings.
  • Coping through Humor: Finding humor in difficult situations can be an effective way to process emotions and experiences.

Conclusion The "Best of Monday 2025" episode of *Armchair Expert* delivers insightful reflections on fame, personal struggles, and the complexities of human relationships, all while celebrating the humor found within our shared experiences. Through candid storytelling and genuine discussions, Dax Shepard and his guests illuminate the messiness and beauty of being human.

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Transcript

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0:00Wondery Plus subscribers can listen to Armchair Expert early and ad-free right now. Join Wondery Plus in the Wondery app or on Apple Podcasts. Or you can listen for free wherever you get your podcasts. Welcome, welcome, welcome to Armchair Expert. I'm Dan Shepard. I'm with Lily Padman. Hi. Today is Best of Mondays 2025. He's an armchair expert.

0:27He's an armchair expert.

0:32He's an armchair expert.

0:39From episode 861, Nikki Glaser. Well, last night I was at the Grammys and my boyfriend, I'm just trying to be very small. Like, I feel like I don't belong there. I don't want people even noticing me to go like, why is she here? Even though I was nominated for a Grammy. But like, I didn't win. I was so mad I didn't win only because I wanted to bring my Grammy to like hold it to be like, I belong. I just wanted to have a reason to be there. So I was being very small. and then people were coming up to me being like oh my god I love people I'm fans of and my boyfriend had talked with me after we were like just kind of doing a debrief afterwards he was like I think you have to remember that you need to go up to people next time you going up to someone will be the same gift as Olivia Rodrigo coming up to you because that was like the biggest gift of my life was someone I admire so much coming up to me to say she was a fan he was like but you could go give that to people and I was like I don't think of anyone thinking of that they would want that from me Did you talk to Taylor?

1:33I didn't. That's one, you know, like Taylor, she's just, everyone wants a piece. That one, I'm just like, I will never be the one to be like, excuse me ever. It's almost rude what I do when I'm in the same room as Taylor Swift because I won't even look her way. She's like tapping you on the shoulder and you're just like. It will take that because I just will never. And everyone goes, go up and say something to her. And it's like she's got there's no way that she's dying for that. And a night like this where everyone's doing it. And of course, she would be so nice. I know exactly how it would go down.

2:04But I just I don't want to take someone's energy away that I require their energy to be put into making great music. I don't want her to make a less great song because she had to be like, nice to meet you. Oh, and like hold me as I'm crying. Give you the full Swifty treatment. Something tells me I can't bother her. I generally after award shows get pretty depressed. no matter what happens because I'm around all these famous people that I put on a pedestal and I kind of see the facade of it all and like the desperation and like, oh. Everyone's the same. Everyone has, they're all wearing uncomfortable clothes and have the fake hair in and I'm like, we're all clamoring to be noticed and a little bit disappointed when we're not and it just, it makes me a little bit sad because I'm like, no matter how big you get, you kind of worry about who's in the room, who's looking at you, where you're seated.

2:50Totally. I kind of go through a depression afterwards. It's seen the magic trick a bit. You realize, oh, there isn't any pixie dust. There is pixie dust. Like there's magical moments where you're like, wow, that person's so talented. They're so amazing. They're like, you know, you know, just even watching Chapel Rhone last night, Sabrina Carpenter, Ray, who I've never had never heard of. Yeah. Watching her was just transcendent. Definitely musicians when they're doing their thing. And if you were watching the people in the room act, perhaps. Yes. But you're just seeing them not lit and not in a riveting drama.

3:21Yes. And they're just people. The reason I brought up the thing is because I wanted to do a full circle, which is, and this is important to say, because I was like a little annoyed and I was upset on your behalf and upset on my behalf because I was like, oh, this is going to be a problem for me. So Kristen is hosting the SAG Awards. Oh, my God. Really? Yes. And she hosted them in 2018. And that's when I was her producing partner and creative partner. And so I wrote her monologue and I did all that stuff for her then. And so she asked me to do that this time. So I went back to look at that original monologue.

3:56I kid you not, there is a joke that is about Marc Maron. That Monica wrote. That I wrote. That is, we didn't have our show yet. That is literally the exact same joke. I loved that show. I loved that show. My jaw dropped. I had no memory of writing that joke. and also I was like, well, this joke is fine. This joke is fine. So that joke has to be fine too. Oh, that makes me feel so good. Like it doesn't mean anything. It doesn't. He killed his closeup. He was such a good sport. Kristen showed it to me. She's like, well, I mean, look at this. We did the same thing. It's so funny. The full circle moment.

4:39I was like, I wrote this exact same joke. It's so nice to hear that because I think that happens all the time where people get mad about something and you've just done it before and no one will ever admit that they've done it before. But even when I get mad, everyone's such a hypocrite. Not that you were. I know. No, I was. But unintentionally. I hope that got to you in our debrief as well, which is as I was listening to the monologue, panicked that I was going to get made fun of, I was doing a personal inventory, you know, and I was going, you have done this many times. Like I have done this.

5:12I have been on Conan making fun of the cast of The Expendables because I had a movie coming out again them and they're easy targets and I can do all their accents. You know, maybe Sly was at home bombed. It's hard for me to imagine that, but maybe because again, in my, in that, in that situation, I'm insignificant and I'm almost speaking in a vacuum. These people won't really hear me. And then I'm like, and I was on a show called Punk'd where we put celebrities in very rough situations and hopefully they acted poorly. I mean, I had no point was ever judgmental. And at no point did I act like I was above that.

5:49What I more was starting to feel was a kind of compassion for both of us. That's really nice. Which is like, I want to get invited to the party. And the way I got invited to the party was like, yeah, you can come to the party if you should. Yes. And I was like, OK, I'll do it. And you get to the party and the people you shit on are there. I know. For years, I'm bumping into Timberlake and he hates my guts. And I'm like, don't you understand, buddy? I was like dead broke and that was my only chance. Oh, my God. So he places you from that. Oh, totally. We've had him on and we talked it all through.

6:24But like, yeah, I would see him for years. And it's like, yeah, that guy doesn't like me. And for good reason. You forget these people have feelings. And generally, the jokes I make are about, you know, at Rose, I feel like everything's on the table because they've signed up for it. We should make a distinction because I heard you talking about it this morning. Yeah. And it's great. You're like, Tom Brady's getting$25 million. He has consented. Yes. Everyone that said yes to the DS, they, am I saying it right? DS? The DS, yeah. Yeah. Everyone who says yes to Cameron, don't make fun of him for saying it wrong.

6:55Everyone does yes to her. Is it the DS? And you go, yes, that's right. DS. I just want to give you what you want. Right back at you. But then I'll ultimately be honest with you. So that's going to track throughout this episode. We have the same approach. Yeah, but there is consent. Yes. And I have been invited to so many of those roasts. And I'm like, I just don't have thick enough skin. I'll just tell you, like, I can't handle it. Don't ever go. I'm very sensitive. Thank God. Like, I don't even think about what's going to be said about me when I say yes to the roast. Like, I put it out of my head.

7:28But even I did the Tom Brady one because it was like, Tom Brady, I got to do it. But the next roast that they threw at me, I was going to say no to because I was like, I'm too old now. Like, when I was 35, getting called old, you could kind of, it didn't hurt. Yeah. I don't feel it. Not really. But at 40, I kind of feel it and I'm starting to see it. And I just don't want I don't want anyone pointing out something about my face or that I have to then go. Talk to someone about. Yeah. In an office and have them draw on me and stare into my eyes and fix it, which I've done and I continue to do. And but I just don't want I don't want anyone else notice.

8:02Like, I just don't want people to pay too close of attention. But then the Tom Brady roast, you just and then you go, oh, good. I'm not the most famous person here. So there won't be that many jokes about me. And that's how it ended up. But the next one, I feel like I'm a little bit more famous. Yeah, bigger target next time. So we'll see. It's going to have to be someone really, really good for me to do it again. It hurts a lot. It does, right? I'm not happy. I'm one of the only people who didn't watch the Tom Brady roast because I can't even enjoy watching it. I just think of myself hearing that.

8:31And I just, I'm very sensitive. Embarrassingly so. I don't read any comments about myself. I've been sober from comments which I think should be a thing yeah yeah yeah yeah like not the general public because I don't think the general public has too many like trolls in their comments but if you're a celebrity or a person you probably know your troll or if you're a civilian and someone's saying you probably work with that person you should have blocked your boyfriend's ex-girlfriend ages ago that's just a simple block but yeah I just I don't I can post things now and not worry and not like go back how many likes does it have because I just go It's none of your business anymore and you don't get to read anything because I can't handle it.

9:09It will destroy me. From episode 893 with Mo Ammer. So Gulf War breaks out in 91. 90, yeah. 90. It was like August of 90. The reason why I remember exactly. Oh, the invasion. The invasion, the Iraqi invasion was then. And I remember it quite well because I was supposed to have my tonsils removed two days before, you know, two days before. Yeah, after they came in. Yeah. Oh, wow. So I was like, damn it. So now for the rest of my life, I still have my tonsils in. Oh, tonsillitis. Fuck you. Might have been a happy accident. No, it's not, brother. They're miserable. I have enormous tonsils. I bet they're gorgeous.

9:54They're massive. They are gorgeous. They are mountainous. You can ski off of those fucking things for sure. You could probably get them out now. I am so scared they're talking about like the way I've, yeah. Adults are supposed to do it. Really? Yeah, it's a really, it's like 50-50 bleed or something. Something crazy like heavy bleeding. Was it someone on here, Tom? Six weeks to eight weeks recovery, no talking. They cauterize it, but you can't feel, you can't feel if it's bleeding down into your stomach. Oh. You can basically. Well, see, yeah. That's all I needed to hear to make it even worse.

10:21But why are the kids more, why are they able to? I don't know. They're just not as mature. I can't see, okay, okay. I think it's not as mature enough. It's an in and out procedure for kids. But someone was just telling, an adult was like really battling whether or not to do it. They don't like to do it on adults because it's bleeding. I went to like the top special at UCLA and they were like, 50-50, they're going to bleed, you know. But you'll be fine. It's just going to take a lot longer to heal. It's like, you know what? I'll just take antibiotics. I'll take my big ass tonsils out of here. I'll just find.

10:51I do a lot of voices too. Like what if it affects how I do all these accents and stuff? I'm like, what if I just end up talking like he sold his time now? I would just be like, my life is ruined. Because I sound terrible. So the invasions in August, the U.S. enters, as I remember, because my birthday is January 2nd. And I got my license in 91 on the 2nd. And it was the only thing that played in the radio when I first. I feel like it was like maybe January 1st of 91. The U.S. entered. Yeah. I had left before that, but go ahead. You left before the U.S. response. Yeah, it was pretty, it was really, really intense.

11:31Because that was the first time I knew that we were stateless, number one. Like, I didn't know. I just knew this happy life. I knew that we were, you know, had family all next. I didn't know anything was wrong. Yeah. Like, we couldn't just go back. That you weren't, like, holding a passport. I was like, why don't we just go to, why don't we just go back to Palestine? Let's go back to West. But, like, why can't we? Right. And they're like, no, we can't necessarily do that either. It's not the best next step. Let's figure it out. And it was the first time seeing, you know, your parents are this, you see them and like, they're your pillars.

12:04Like they're, they're always in control. There's nothing ever wrong. Seemingly know everything. Seemingly know everything. And to see them so worried. Yeah. And I remember this to this day, that call at 6 a.m. I remember the phone ringing, you know, at those days, the phone, wake up the entire house. You know, I was like, who the hell is calling? And I remember getting up and my mom picking up the phone was like Saddam has invaded Kuwait, hangs up. And now everyone is out to try to get as many resources for the house, food, rice, water, you know, whatever you can get. Yeah. To just store it. And yeah, that's when everything changed.

12:39And they got to our house at one o 'clock in the morning and I was past, I was asleep. I've slept through the whole breaking of the door, ransacking the home. They were threatening my mom, my dad, who's in this bedroom? who's in his bedroom they were pointing at my bedroom and they were threatening they were going to throw a grenade in the bedroom like tell us tell us tell us and uh and you know my mom and my like they were trying to figure out who works at the equator oil company since the whole reason of their invasion to begin with is the site supposed siphoning of you know iraqi uh uh oil and whatnot whatever was that their premise they were diagonally drilling in is that that's I don't know what they were saying.

13:20I don't know what exactly is. It feels like, you know, yeah, it's a bigger conversation to me now. As a grown ass man, I see what's everything going on living in America. Now I know like who's been putting all these people in power and doing it. Let's talk about that thing. But that was the premise is that, you know, Kuwait was stealing from them and he's there to take it back. That's the idea. But then since it's the Kuwait oil company, so our neighborhood was hot. First stop. Yeah, first stop. Absolutely. And it was all about collecting people who are, you know, who could help manage and turn over the control of it.

13:55Your dad's like, I just do telephones. Well, that's the biggest fucking thing. Right. Communication. Okay. That was like one of their probably on their top five list. Oh, wow. You know, of, you know, transferring all communication to where? Right. Transfer it to at all, you know? Yeah. So my dad had one choice, either do it or we, you know, potentially your family is at risk, you know, might take them online. Who knows? You're not going to find out if they're bluffing or not. Yeah, exactly. You're just going to say, yeah, that's me. What are you going to do? Like, what is he going to do? So he was forced to go in and redirect some of it from what I've heard, some of it at that time.

14:34And he regrets it. He doesn't, didn't feel good about any of it. Well, he had to protect himself. And he loves, he loves, he loved Kuwait and he loved the people of Kuwait. He loved everything there, and he was just saddened to see it all happen that way, but he was also just protecting our family. So, like, soldiers would show up early in the morning at our house and just constantly all throughout the whole street. It was pretty regular, but I felt like our house was like a spot, you know? Yeah. It became that, and we played soccer with these guys. Like, they were just, you know, had me like, hold the machine.

15:05I was like, I don't want to hold the machine. Yeah, yeah, yeah. You know, it was that weird, like, different life just. Everything changed. Right. And trying to evaluate, are these guys mean and evil? They weren't. Right. But when they first show up with the guns. They have moments. They have moments. I remember this guy, he had a thick stash, huge. But I was really fast as a kid and I played tons of soccer. So I was killing these older guys. I was killing them and he just, boom, he just socks me real hard. And I remember being laid out on the ground and I look up and I see him. And this is how he felt like he was laughing.

15:36He goes, uh, uh, uh, uh, uh. And I was like, what? Like a boss of evil, bro. It felt evil. I know he's not, but he was just like fucking with me. But it just, it really, it just, it just, I can't forget his face. I can, I can, if a sketch artist was sitting here, I could draw him. It's that kind of, you never forget. From episode 9-11 with Brad Pitt.

16:04You know, I've never had a gay experience. I kind of missed that window. But if I did, yeah, it wouldn't be you. Oh, man, you had me. I was like, wow, he's going to say it. I was like, Dax is going to die tonight. 14th or 15th. I don't want to brag, but you're going to need to build up to me. Oh, boy. I do recommend you start with some starters. Now, is this true, that you left college a week before graduation? No, I actually went through graduation. I just didn't finish my last week of classes and actually graduate. But my parents were already coming. Oh, you went to the ceremony, but you didn't graduate.

16:44Fucking walk the line, hat and all, cap. You wanted to be able to throw your hat. Well, sure. It's very fun. I'm going to miss that. That's a crazy fucking decision. No, because I decided, come to L.A. Uh-huh. You only had one week left. I had one week left, but what's the Spike Jonze movie? Adaptation. Remember when Chris Cooper goes, he talks about, he's into, what is the flowers? Yeah, the lotus. Yeah. Yes. Lotuses? No, it wasn't a lotus. Orchids. Orchids. Yeah, yeah, yeah. And he talked about his former Jones was about fish or some kind of fish breeding. She said, I think it was Meryl asking him what happens.

17:19And he says, done with fish. Yeah, yeah, yeah, yeah. It felt like that for me. It just like, done. I don't want to do this. I talked to a friend. It never occurred to me. I was kind of lamented that movies weren't an option. I'd always loved movies. I met this friend whose dad had a condo in Burbank and said I could stay there for one month. And I went. Green light. I'm going to it. I'm going to it. And he moved to Beverly. What car did you drive out for that? Datsun 200SX. Oh, wow. With the bumper hanging off. Okay. It wasn't in great shape. Do you still have it? No. Sometimes it's fun to have those old original.

18:03Do you fantasize about getting any of the stupid cars you have? because I had a 91 Honda Civic DX for a decade here, and I want to get one and make it fucking fast. I was just looking at my dad at a 74 Monte Carlo, and I was just looking that up. You got to get it. Just looking it up. You got to get it. Just for fun. Just a little tribute. How often are you scrolling those cars? Be honest. Yeah, just bring a trailer to your porn. Almost as often as I'm scrolling Zillow. Yeah, I know. Zillow will really get you. I love house porn. House porn, car porn, bike porn. Well, you've been in this situation for a long time, but it's for so long, it was just I dreamt about it.

18:40And then I could do it. And then I did it. I bought too much stuff. I saw the toys out there. It looks fun. It looks fun. This is me now, like, constrained. So I have these, like, rules I have to have in place. Like, I have to look at the car, like, 10 times. And I got to want it still in four months. You know, like. So you make sure that you put the time in to make it worth its while. That's right. I, I, I, I, cause I'm dangerous. I get on, bring a trailer and I'm like, oh my fucking God, I need that thing so bad. Okay. So you drove out in a Datsun. I did hear a funny story about you, um, wanting to get your SAG card and interjecting.

19:16Oh, I got shut down so hard. Will you tell Monica that? Oh, did I get shut down? I was doing extra work for about a year and a half before I even got into, got to do something real. I was doing, I was an extra and I was thrilled. I loved it. I couldn't believe I'd be on set. And I started that. And I mean, when I landed in Burbank, I got the paper. I went to McDonald's. I had$275 left in my name. There were three extra agencies. You could pay them 25 bucks and you were in. I found it in the paper and I got in. And the next day I'm going, I'm rolling. I'm doing an industrial, industrial like video by the end of the week.

19:51Yeah. And, and I get this, I get this gig. I'm already inflating what happened. I'm an extra in this movie. I land this role. I land this job as extra. It's a waker. But the funny thing, when I started, I put them on like a resume like they were real. Yeah. And it still haunts me. Oh, sure. It's still like on my... Anyways. That's great. I'm like a jackass. And it's a restaurant scene and it's the main characters, Charlie Sheen and D.B. Sweeney and a bunch of other actors that I wasn't necessarily aware of. And I am the waiter. I'm supposed to bring up champagne and pour champagne. And they show me how to do it.

20:31You got to pour. Yeah. You spin. You wipe the thing. I said, great. That's more than an extra. I come in. Well, it was a chosen extra. I got chosen. I was chosen. I got put forward. Oh, my God. And the whole game was, how do you get your SAG card? Yeah. Because you can't get a job if you don't have your SAG card. But you can't get your SAG card unless you've had a job. So it was this catch-22. Specifically, you need to speak. Yeah. You got to speak. That was the finish line. Barrier to entry. Yes. and like a jackass, they're having the scene, they're doing the scene. I get to the last actor and she seemed lower on the totem pole.

21:06Like I thought maybe and literally the scene is going on. I pour her champagne and I go, would you like anything else? I want the dailies from that. Listen to this. It was Kurt, Kurt, Kurt. First AD runs over. You do that again, you're out of here. Oh, my God. And it's just Shane for the rest of the night. That's so funny. Took a shot. Stay tuned for more Armchair Expert, if you dare.

21:45From episode 949 with Dominic Fike.

21:51Okay, but you didn't get to cocaine or breaking out his arrest. Oh, yeah. So you're in there focusing and doing wonders for your songwriting. But I'm in a room all day and I'm trapped all day. And even now that that's my job, it's like I still know that I have to step away sometimes, even if I want to. I know that it's healthy to step away. Yeah. Isolation is. It's a bitch. Yeah. Yeah. Yeah. So I start using everything I can that has a short span in your stream. Coke is like three days. Yeah. Is that what it is? I don't know. I was when I was looking it up. Okay. Yeah. I wasn't taking a lot of piss.

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22:24test when I was smoking crack. This may surprise you. I didn't hold any employment. You know what's funny? Me neither, but I think it's something in middle school that you do with friends when it comes to weed. You guys discuss the shelf life of drugs in your system. I didn't know weed lasts like a month. I know that one. Everyone knows that. Every guy knows that. And meth lasts a while in your system too. But I don't know the coke thing. I should have. Coke's one of the quicker ones. So I'm doing coke. Doing a lot of coke. I guess you are on house arrest. That's true. I'm bored. and like the girls are always at work and I, and their mom lived there too, but she's always at work.

22:59She's trying to get me to go to school. She's like, Dom, you need to do something with your life. I'm telling her I'm making a mixtape kid with a face tat, smoking dope, doing Coke in her fucking department, talking about a mixtape, you know, I'm not necessarily investing on that. No one gave a damn. No one gave a damn. And then I get called in for a thing. And it's right as I finished the last song on the mixtape, I'm up doing Coke that night. and the dude calls me at 7 a.m. He's like, Dominic, another drug test and I'm thinking like, oh, I just did it. So it's probably not even in there yet.

23:31Oh, like I just did a five minute... Like, what's up, Pete? Give me the cup, motherfucker. He gives me the cup and I just failed and he put cuffs on me right there. I'd never been so in disbelief. I was like, we thought you had it all. Well, the coke will do that, won't it? That's the great thing about coke. It makes you optimistic. That's why it's a relief. And then I went to jail for a while And during that time in jail, I released the mixtape. Yeah. So how was the time in jail? You were in county. It's awesome. It was great. I'm not even kidding. Really? I had a good time in jail. Again, this is a stereotype, but I'm worried how cute you are.

24:04I'm a little worried about how cute you are. Well, that's scary. I know. I hate to perpetuate a stereotype. Okay. So it's not really like that. I'm a little nervous. Okay. Tell us. There's this thing called like PETA, PETA, PETA, PETA, PETA, PETA, something like that. It's some four-letter acronym that is against prison rape. Okay. So we got some action in there now. We got some protests. Okay. It's like D.A.R.E., but it's like they kept doing D.A.R.E. Oh, wow. And it was a huge nation on it. And it worked. Yeah, yeah. Because I was in, yeah, I had full long hair. This was before I, you know, I was like 20 in there.

24:36Oh, no. I was a piece of ass. Yeah. Yeah, there we go. You're a piece of ass. I was. Just call it what it is. I was. I was. in a violent block because of my charge. So my bunkie was just a, murdered his family. Okay. Hilarious though. Sure. The funniest guy. Like the funniest guy. Well, if you can't laugh about murdering your family. You know, if you can't laugh with him because you killed them all. Oh my God. Wait, how old are you at this point then? I'm like 20. You're 21. 21. Okay. And how long were you in jail? Like a year. Okay. Yeah. So, you know. Wait. Murdering. I did have one question.

25:15and We Blue Pass. Did you watch Florida Project? No, I never watched Florida Project. I was never into people like making their projects about their like movies about my town because they always did it wrong and I just didn't want to be let down and pissed off. I don't think you will be with that. I hadn't seen it when everyone else saw it, but then I loved Enora. Yeah. And then so I went back and watched Florida Project. Florida Project's better than Enora and I love Enora. Florida Project is fucking... That's a crazy take. It's awesome. Sean Baker's amazing. Did he do... Oh, he did Florida Project.

25:44Yeah. He did Florida Project. Okay, we love Sean Baker. Yes, and it has this impossible thing that kids have. Once every 30 years, someone captures little kids being little kids. You're like, how did they get this to happen? It's magic. It's the first time you saw Dakota Fanning. What the fuck's going on? Yeah, I Am Sam. That movie, I Am Sam. Drew Barrymore, E.T. Drew Barrymore, E.T. E.T. So, you piss hot, you go to county, you release the music. Now, this is so improbable. By the time you get out? Yeah. Yeah. By the time he gets out, there is a bidding war to sign you. And you sign at Columbia for$4 million.

26:24What? This is a wild one. This is up there with. Keehee Kwan, yeah. Keehee Kwan. Yes. He's on a refugee ship. Oh, wow. Within a year, he's flying first class to fucking. With Steven Spielberg. To be in Indiana Jones. Wow. So, yeah, this getting out of prison to a$4 million contract, how do you compute that? Yeah. So I don't know. It was kind of like the first of its kind in that span of time to happen to this bidding war thing. I'd never been a part of anything like that. Because it was big on SoundCloud, right? You had put it all on SoundCloud. Yeah, I put it on SoundCloud. And then my manager, Reed, who's still my manager to this day, takes it off real quick because he sees it starting to garner attention.

27:04Yeah. And we had a couple of suits reach out. We'd never been in contact with anybody like that. I've been releasing music for five years at this point, you know? Yeah. All over it. Any way I can get it, I'm releasing it. so then people start reaching out and these dudes start flying from california to visit me in the jail no like i'm not even kidding you i'm i'm at the front like this type of shit like yeah with this dude that's like hey dominic you ready to be a millionaire yeah and you're like i'm homeless i'm not doing this for a penny under four million you can take three million and shove it in your what had happened what had happened was my mom is in jail and my dad's in jail at this point for 20 years both they're facing 20 years because um my family this whole time my family they're huge heroin dealers huge heroin traffickers my dad sean my stepdad sean's a heroin trafficker like we're all chilling at one point and we've been doing this for years living in hotels selling coke or whatever it worked out it put me through school you know at the time and then they the doors all the doors get kicked down at our hotels and at our other houses and everyone's taken to jail marshals you know it's it's in the news i'm seeing them both i'm like oh man they're fucked like 20 years each.

28:05So I'm in jail too. And my sister's up for adoption because of this. And my brother's in jail. And I need to get my sister out of adoption. I need to get my mom out of jail and I need to get my stepdad out of jail. So, you know, each lawyer for them is 200 grand, 200 grand a piece. And then to get my sister out, I'm still paying for that to this day. Wow. So I'm like thinking about my position and I'm homeless at the time. You know, and I need some fucking money. Yeah. This is my work that y 'all are buying. All this is in my head, you know, at the time. And it wasn't that I came up with like$4 million.

28:41It was just more like these dudes. I'd never seen money over$1 ,000. Yeah, yeah, yeah. So motherfuckers are like$200 ,000. I'm like, that sounds like a not real number, I guess. Cool. I'm not pushing it up. Another dude flies from another label, comes to the jail, says a bigger number. And then I didn't even know this was a thing. I tell that dude that the guy said a bigger number. Yeah. This motherfucker goes with a bigger number. I'm like, wow, I feel like I'm a, you know? Yeah. You're in Jerry Maguire. Jerry Maguire. Dude, that movie is so funny. We get to the point where we're in L.A. and on top of the Columbia building, or the Sony building, because at this point Rob Stringer's involved, like the dude who owns Sony.

29:21He's like, all right, who's this motherfucker? Like everyone's throwing this money around. Who's this guy? He comes to meet me. We're in a meeting, and at this point I got my, like, I got the, I know how to do this money thing. I'm forgetting. So I'm in the room and I'm like playing them songs and they're like, oh, these are so good. And then I'm like, yeah, well, you never know. And I'm about to walk out and Rob Stringer's like, so what, are we doing this or not? Because he's a businessman. He's like a real, I respect him so much. He's like, are we doing this or not? I'm like, well, I don't know.

29:47And Ron's like, maybe we could. And he's like, no, no more millions. Are we doing this right now? I'm like, yeah, I'll do it right now. And we just sign it. And we pop a bottle of champagne on this rooftop. It's me, Rob, and a couple of my friends. And then I go into the bathroom. and I'm like yeah I gotta piss because all the champagne and I'm looking at my phone the bank account and I see the number jump at the urinal and then from then on I just don't remember it's been like seven years of from episode 879 with Dove Cameron

30:19were you having any guilt about being in Burbank yeah I mean I it was a weird thing because to be completely honest I tried to mend my relationship with my dad a lot and I think there's this thing that happens with depression a lot of people who are depressed um where they are perpetually pushing people away yeah and for the entirety of like 13 and 14 and 15 I was really trying to connect with my dad I think you know he was always a depressive person like my mom and him met and he was like I'm super suicidal and she was like okay I'm 20 we're gonna try to get you out of this you know like boy yeah so so it was always sort of um there but I really at 13 and 14 and 15 I was really just like I miss my dad I know something's weird he doesn't answer when I call well the most heartbreaking part from it would seem to me is that you at least had the fantasy at all times this will get repaired one day yeah I keep trying but one day he's going to be feeling better and I can get it repaired yeah sorry you know and then they go like uh oh god yeah I'm not going to be able to repair that is fucking yeah really sad yeah yeah it's true it's um it's it's also like I think about this a lot because I was so young and I like I have a memory of him like coming to stay with us once in Burbank um and I just remember like thinking all the color had left his face and I didn't know like he was drinking so heavily and all of that um and I remember being like young enough like 14 he was staying on like a little blow-up mattress or something in our living room and I just came out to like like he wasn't looking at me in the eye like it was all this stuff that I like didn't really I thought he was mad at me right yeah yeah and I like came to like say good night or like lay down next to him or something and because I was still like a very young 14 like I wasn't like uh like mentally I was mature but I was still like I wasn't dating I was I was very like my parents kid and I was very insulated and like I don't know maybe like very protected and I remember like laying down next to him just for a second to be like cuddle time, like routine.

32:53And he like didn't really move. And I remember him being like, I think you should, you should go to bed. And I was like, and I remember receiving that as just like such a rejection that like he didn't want to. And I, and I didn't know what it was. Like, I truly thought he was angry with me for something. And you know, when you're a kid, like you blame yourself. Of course. You really blame yourself. And so I was like, maybe I'm behaving badly or something. I didn't really get it. Or I would just feel guilty that I'm pursuing my own life. yeah like is he mad that i'm pursuing my own life and i'm i mean he was always like kind of vaguely supportive i guess like he was worried about me more than anything like he was worried that i wasn't going to be able to survive in hollywood um and i knew that but he was never like i the thing was i had gone back to see him after i had lived in la for a year and i stayed like at our home for the summer at our family home and i i went because i wanted to spend the summer with my dad and I wanted to see him and we hadn't seen each other for so long.

33:51And I remember him doing everything he could to get me to not stay with him. Like he would send me to stay with my friends and I actually probably didn't want you to see him. Yeah. And I remember like, he was like a famously, um, like tight walleted man. Like he was always like, you get$100 for clothes every year before school. And if you grow out of them, that's your problem. Yeah. You go secondhand He makes six outfits out of this. Yeah. He's like, if you grow, that's your fucking problem. And then the rest, like you have a sewing machine figured out. And I was like, all right. But he, the, the year, the, the summer that I stayed with him, I remember he was like, just giving me money, like just cash money to get out of the house.

34:31And I was like, that's so bizarre. And I, I didn't really realize that he had already sort of put a plan in place where it was like, he didn't need it anymore. No, he got rid of all of the animals. He was getting rid of all of his money. God, isn't it weird to think of someone planning for that long? Something like that? Yeah. It kind of goes against my stereotype of it, like overwhelming you in a moment as opposed to. Right. Well, it might not have been as consciously planned as just like, I don't want anything. Like you're. You've lost even the desire. Yes. You've lost the desire to even care for anything or have anything.

35:08I still go back and forth on that because I found out later that he was paying like my friend's mom to like get me groceries and like basically was just like pawning me off on another family. And I was so I honestly just thought he was mad at me. Like I internalized it like for two years that he was just mad at me. And I was constantly trying to fix our relationship and reach out and he just wasn't having it. um and so i i don't i don't think at the time i felt guilty for being in la so much as like even when i was on the island still he was not really wanting to see me and so i was kind of like i'm always here i'm always wanting to connect with you your side of the street was clean and I found out also that like he had attempted something really publicly and my mom kept that from me and that was like a big sort of turning point in like my mental health was just being like what do I not know is going on you know right right and my mom was probably right to keep that from me but of course when I was like 14 or something I was like what the fuck so I really didn't know what to think of it like he the last thing he texted me was like I love you Chloe and then it was like we got a call the next day and it was like yeah it's really crazy I honestly don't like talk about it too much yeah understandable not because it's hard honestly because I do talk about it but I talk about it with this kind of like here are the facts yeah you can disassociate a little bit so I went into therapy for the very first time like three years ago or two whatever it was oh really wow weirdly since I was in recovery for so long and I was like well I'm getting everything I need from there but whatever I did and yeah I I can tell you my story I can tell anyone my story yeah and it is it's a list it's a timeline yeah it's like then this happened then this happened and then in that therapy session as I was talking to him for the very first time the emotions were attached to the timeline yeah and they just are not generally for me uh yeah so I can relate to like these moments where like oh okay the emotions are here now with the story.

37:20Yeah. Yeah. I think also like, I think also some, it's, it's really hard to, a lot of the time, like trauma is very sensationalized. I'm sure, you know, I've become very protective of that over the years because I used to be much more open about speaking about it. Um, I had a friend who died very publicly, um, in the last few years. And that was when I sort of tried to reorient a little bit my autonomy over like where what spaces I share that much well my therapist said to me he's like you know some stuff you you can keep for yourself not because you're you're hiding it out of shame but just it's yours to keep and you should keep it for yourself like also having it for you in a weird way which was a new concept yeah it's sort of the opposite of what we were talking about earlier which I was actually going to say that Like I think it's actually okay, not out of shame, but when we were saying like sharing is important and of course it is, but it's okay to have things that are just yours.

38:18Yeah. And it doesn't mean like it's your secret. It's just like it's yours and you can protect that if you want. Well, that's your life. It's just like sliding that line back and forth. And it's like, yeah, I felt comfortable with it here and now I feel more comfortable with it here and it'll probably change again. Yeah. And it's fine. And there's not a right or wrong. It's just like, yeah, am I betraying myself? Do I regret it later? Right. You did make me cry today, though, because I was seeing the tattoo that you got. And I have little girls. No. And I say that same thing to them all the time.

38:53Oh, my God. You're going to make me cry. That's so cool. And I was like, oh, my God, I can't. if they had to tattoo that on them at some point because something went sideways. It was just heartbreaking. What is it? What is the tattoo? If you don't mind sharing. It says we'll be friends forever. Which is just like the sweetest.

39:20Oh my God. I think it's like almost every time I'm like, you know, we're going to be best friends for the rest of my life. Yeah. Yeah, unless I get a procedure, hopefully. I live for 180 yeah you gotta work on that maybe I can do with them the whole time yeah I'm like we're fucking best friends from this day to the end well and that's what it should be right like I was I'm so like moved to hear you say that about your girls cause I oh yeah cause I truly was best friends with my dad like and he really like he tried his best you know there's probably equally sweet relationships but I find it hard to believe there are stay tuned for more armchair expert, if you dare.

40:06From episode 923 with Alexander Skarsgård.

40:13I was out here forever before I started working. Okay. Like a painfully long. I booked the first audition I went to. Zoolander? Yeah. That's fine, because then nothing happened for a long time American film-wise. We don't need to talk about that. Let's just focus on the fact that I booked my first audition. That's very Ashton Kutcher of you. So it's one for one. You should have gone back to Sweden. Well, I did. Oh, you did. I was working as a hot barista in Stockholm. And then I came. Dad was shooting a movie out here in L.A. And we all came out just to visit. And my dad's manager, she's like, I'll send you out to an audition if you want.

40:55And it was for Zoolander. Yeah. Um, and I booked that baby. Yeah. I remember thinking, cause again, I didn't have representation out here. I'd never been on audition. I'd never auditioned in Sweden for anything. I was just like, oh, I guess this is how Hollywood works. You walk into a room and Ben Stiller is sitting there and then you're like, all right, let's go to New York. And then, you know, listen to a little wham and drive down and have a gasoline fight. Wow. So then I went back to Stockholm and my dad's manager was like, all right. That went all right. Yeah. If you wanted. We could build on that.

41:30Yeah. You should come back when, you know, you're done with your, whatever you're doing out there and we'll send you out some stuff. Serve all those coffees. Yeah. Then I came out in, I think, 2003, maybe. Okay. Incredibly naive thinking like, all right. I'm ready. All right, Hollywood. I finally decided. You're welcome, Hollywood. I'm here. Yeah, here I am. I'll take it. Yeah. Yeah, yeah. You'll find me at Starbucks on Sunset Boulevard. Come get me, Spielberg. And he didn't. And no one else did either. Yeah. Because Zoolander is 2001. Yeah. And Generation Kills 2008. We shot it in 2007. Okay.

42:04Yeah. It came out in 2008. So were you here the majority of those six years? Yes, sir. Yes. Okay. This is what I want to live in because, again, I did that. It's the most relatable part of your story. Yeah. I like to be relatable. Yeah, we all do. But I didn't have on top of that, well, my dad's great at it and he's really successful and I should be able to do this. Was that a compounding or was it fine or was it grueling? The dad relationship wasn't really grueling or that wasn't something that I felt that I, I didn't feel like an external pressure to like live up to or reach his level of success.

42:48It was hard because I couldn't get a job. That was hard. Yes, yes. and the fact that I came out being very naive thinking like oh it's super easy yeah and Zoolander was a great experience and it was also like a super fun movie fuck yeah and then I found myself like auditioning for things that I didn't really like but I was also in a position where I had I was at another agency then um and I was constantly worried that they would drop me because I wasn't booking anything yeah and you're like paying to get new headshots all the time you're just kind of yeah and they you know Pilot season, I would audition a lot, not book anything.

43:29And then it would be like weeks without an audition. So when they finally called and they're like, we have this job, audition. Even if I felt like this is terrible and I'm so not right for it. You had to do it. You had to do it. Because then like I was constantly worried. They would be like, well, you know what? I think it's time for us to part ways. Yeah. And that's, I don't know if you have to do that, but like auditioning for stuff that you don't believe in. Oh. And where you feel like you're completely wrong for it. you feel dirty in your soul like it was horrible. Yeah. You're already worried you're not good enough to do this job.

44:00And then when you go in and try to put your square peg in that round hole, it just is like, oh, my God. No, you think sometimes you think you're too good to do it. You're like, I'm better than this horrible piece of shit. And then you don't book it. Yeah. And you're like, oh, my God, what is this like? Yeah. And then you get from there to being like, well, I'm clearly not better than this horrible piece of shit. Yeah. I'm so wrong for it. And I know I'm not going to book it, but I still have to go into that room and be humiliated. Yeah. So, yeah. Well, the first couple of years, I went out with a bunch of friends from Sweden and we kind of had a little, first we rented like a little pool house in Santa Monica.

44:39So four of us lived in a small pool house with this Swedish lady. Yeah. And then we're renting a small apartment. So we had each other. I didn't know anyone else out here. Right. So, and we were definitely not plugged into the city or the nightlife or like. Okay. We would, yeah. On Saturdays, we would like play ping pong in our pool house in Santa Monica and drink beer and then take a cab into Hollywood to try to get into a nightclub knowing that we wouldn't get in. Yeah. Four dudes. Yeah. Get turned around and then happily get back in the cab and go back to Santa Monica and keep drinking beer, play more ping pong.

45:15So that was like our weekend routine. Having done that, do you ever now like this happened to me? I went to Craig's and I, you know, there's so, do you ever go to Craig's? Have you ever been to Craig's in West Hollywood? It's a restaurant and there's always paparazzi there. And it's always like, it's a hotspot. And I just imagine you going to Craig's now or coming out, like it'd be a frenzy. It'd be like a whole to do. And I wonder how you can, can sort of reconcile that as someone who would just like stand in the line at the club and never be able to get in. and now they're like, they would die for you to come in.

45:52Is that, can you like integrate that? No, I just remember after a couple of years, we met a Swedish girl out here who like, and she was plugged into the city and she was so nice. Yeah, she moved out of here when she was like 20, but she was very plugged into the city. Okay. And she would take pity on us. So she would like, I remember like, we would try to get into a nightclub, couldn't get in. And my buddy called her and was like, like, Helena, do you know anyone here at the club? Can we get, and she's like, I'll be right down, boys. And then she would come down in her sweatpants to just like sell the pointer to be like the bouncer.

46:29It was like, hey, can you let these guys in? And he's like, all right, Helena. And then she would go back home. So she wouldn't even go out. Like, it was so sweet of her. That was nice. She knew that we spent years going like into clubs, not getting in, back to Santa Monica to play ping pong. So a couple of times we did like have the luxury of getting in somewhere. I can tell you how I integrate it. I wanted that. Yeah. And I have it. And I love that. I love that when I drive by all these places that for years kind of haunted me, like I'd be afraid to even try to get in. Yeah. Just knowing as I drive by, oh, they would let me in.

47:03Yeah. I love that. But I can't. And again, this is the Yantelog, the Swedish thing. I can't walk up to a bouncer. Like if there's a line, I can't walk up and be like, what's up? Let me in. Google me in. Succession, bitch. Dude, Google me. Yeah. Google me. I dare you. But you wouldn't have to. As soon as you get out of the car, they're going to be like, oh, oh, Alex is here. We got to get him in. Yeah, but the sweet of me would be like, look down, back of the line, shut up, wait for your time, your turn to get in. It's all wasted on you, really. It is. It really is. Because I don't do it, but I do know what it was like to be so on the outside.

47:44and when I drive by, I'm not even going to the places, but I just go like, oh, you could. You moved here and you were looking at it and you couldn't have it and you can't, you have it now. What that was, I remember it being a conversation that we often had as we were like waiting for the cab to take us back to Santa Monica. We would be like, in 10 years, if we stand here on Santa Monica Boulevard, you think we could get into any of these clubs? One day. That's the dream. Would one of us be able to get the others in? Can we leave Helena alone? Can we let Elena sleep? Can we take her off the clock?

48:18Yeah. Yeah. It's a weird thing to get to that place here. Yeah. From episode 960 with Jennifer Aniston.

48:32We're talking about kids and this might be a no-no, but I'm curious. Hit it. You can ask me anything. Okay. I froze my eggs twice. twice. It went very badly. I did a podcast about it. It was, you know, following the journey, it was a whole thing. And I'm 38 and I am single and I'm, you know, feeling like time to start making some big decisions. It's kind of feels like now or never ish, ish to even try with some of those eggs. And I'm starting to just feel like, I think it's, I think it's never. And why? Because now, like. Can I ask you a bigger question? Yes, please. Are you doing that, the freezing?

49:21Yeah. Have you always wanted children? I've always not known. If you wanted them. Yes. So it's not like we had Chelsea on that podcast, Chelsea Handler, who I know we both love. And she, you know, she's kind of always been like, no, I don't. Very cut and dry. Nope. Not my thing. Not her thing. And I like, I respect it and I wish I had that because it's not that. It's very much like, oh, but I do like, I'm very close with their kids. And it's like, oh my God, to have one of these, that's mine. You know, you get, you get kind of wrapped up in it. But also my life is also very full. What you just said about all your friends and your life, I have the same thing.

49:59So it kind of feels like I, maybe it's okay that I don't. And I, I wonder, you've said like, you know. Yeah. you're on the other side of that. And I wonder if there's peace there. Oh, it's so peaceful. You're like, I'm good. It's so peaceful, but I will say, well, there's a point where it's like, it's out of my control. There's literally nothing I can do about it. Yeah. And when people say, but you can adopt. I don't want to adopt. Yeah. I want my own DNA in a little person. Yes. And that's the only one, selfish or not, whatever that is. I wanted it to come. but is there the moments of, well, this goes around into, it's probably a topic I don't really want to talk, but discuss, but when you meet someone and you go, God, I would have, we would have made some good kids.

50:52Yes. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Of course. So that might come up and then that'll pass within three seconds. Right. Right. Right. And then you're like, but guess what? You'll plan a trip to Mexico. Yeah. You'll be on that trip. Just take a look at that vacation for five minutes and you're like, oh, good night. Bye. See you later. What are we going to watch? Yes. Okay. I like that. So it's because it's like a, it's a romanticizing. But once you are on the other side of it, there is definitely a, yeah, because it's out of your control. Yeah. Just wasn't in the plan. Whatever the plan was.

51:30Exactly. I do think some people, though, like can't. Let it go. Let it go. And I worry, I guess that would be me, but hope. Come over and I'll help you let it go. Okay. I'll take that invite. Yes. Yeah. It's a lot. It's a lot. It is a lot. And by the way, it's very emotional, especially in the moment when you get, when they say, oh, it's, that's it. Yeah. Because there is a weird moment when that happens. Yeah. This is getting too dark for this podcast. No, no, no. But it's like, it's, there's a moment when you are, it's actually, oh yeah, this is not even viable. Exactly. Time is up. Oh. That's probably a blessing and a curse.

52:07It is. It probably hurts really bad. Yeah. And then probably you move into acceptance mode and it probably is liberating on the other side. Totally. I would guess. Yeah. I ran into Sandler and Spade in the room right outside. Wow. And I knew Sandler from forever. Uh-huh. You knew him pre-Friends. Yes. Oh, wow. Because he was very good friends with Charlie Schlatter who played Ferris Bueller in the television version of Ferris Bueller's Day Off. Wow, you guys go so far back. So we met at Jerry's Deli in like 1912. Wow. 1912. Just before the Spanish flu. Just before. Right before. So, yeah, so I don't know why I had this self-righteous attitude of like, I don't know if women are treated the way they should be treated on this show.

52:51It's a very male-dominated, and I mean, I would love to be here if it was like in the Gilda Radner day. I mean, this is what I, my semi, the brain that semi remembers things that are back that far. Yes. Something like that. Okay. I got, okay. That makes sense. And then, and then it was like, well, I don't remember what happened in there. And then I can't remember, but I just remember friends then happened. And then that's where I went. You really fucked up. You chose wrong. You think so? Oh my God. Yes. Well. Shit. People say regrets. I could be interviewing you and I could be going, so you turned down friends for us.

53:30And people would be like, oh no. That would be the saddest story of all time. Yeah, people. Yeah. It all works out. It works out. I don't think there's ever, everything is sort of meant to be. From episode 846 with Adam Scott.

53:53so obviously since then you have done a ton of stuff but um severance is like the most spectacular thing and as you know because chris and i sent you voicemails yes almost after every episode yes i'd like to play a couple of these hey so we're in bed and we just had a quick Hi, we just had a quick question. Are you guys fucking drawing this new season? Is that what's taking so long? What in the goddamn hell is taking so long? These are the kind of messages you would receive after I've read. You son of a bitch. You wanted the compliments? Well, here comes the fucking complaints. Belle and I just sat here on the edge of our seat waiting to find out what happens when you guys come to.

54:40You fucking prick. You piece of shit prick. And that goes for Ben, too. Losers. Oh, buddy. Are we fucking pissed that this episode just ended when the switches were thrown? So you wanted the fucking cake, and now you got to take the rat poison, too, you piece of shit. Okay, so that's kind of an album. Was that for the finale? It was, I think, one before the finale. Oh, the one right before. Yeah, yeah, yeah. And this ended up being three. Oh, another thing. It's going to be a long fucking week for us and for you. Yeah, because we're waiting. So either block my number or get used to this shit. Fuck you.

55:20You piece of shit. Came in the last ones. Quick update. You'd probably find funny. My wife just ran through a plate glass window off the second story of our home and was rushed to the hospital. You probably want to know if she's still alive. I will tell you next week. I have all those on my phone as well I want to play your response just one of your responses which is so good you can't imagine how much pleasure it gives me to have the both of you over a barrel like this I may as well tell you now that the entire season was created just to frustrate and destroy the both of you eat shit the bitch is so fucked oh yeah Naomi hopped in there Oh, that's cute.

56:09Yeah, there's a scene in the show, actually, where we were on the side of the road at the site of my wife's car accident in like the seventh episode. And just by sheer coincidence, because we shot the whole season at once, it was on the one year anniversary of my mom dying. Oh, wow. Which was completely, and I didn't realize it till that day. And so there were things like that where I could pretty directly just let out how you were feeling. Yeah. And process. When you shut the door to the apartment and you go, yeah, we got some dealing to do. Are you overcome with fear for that process? Or what's your reaction to knowing that?

56:55Like, oh, we're going to go through some stuff now and we're going to be by ourselves. Yeah. And we're going to get into this. I think that I'm a person who tries to compartmentalize and push things to a later date. And so I think I busied myself with the getting ready for the show and the election was about to happen. And so I was preoccupied with that. And so I closed that door and was like, oh, shit. And really felt the loss right there. Like, oh, there is a giant elephant in this room with me, but it'll be there. I'm here for eight months or whatever. It'll be there. I'll be fine. And eventually after a few weeks and just hours of alone time because no one was socializing really.

57:52and restaurants. It was so weird that I really did have to figure it out there. And I didn't talk to a therapist while I was there and I really should have. I did kind of, in a way, sort of come to terms with it and come to terms with the fact that grief is something that is a flat circle in one way or the other. It stays with you. And sometimes it feels like it happened 10 minutes ago and sometimes it feels like it happened 50 years ago. And sometimes it's a surreal that that person is no longer in your life. It's just like unbelievable. It's really hard to imagine someone exists and they don't.

58:36As dumb and simple as that is to say, it is so weird that you can exist and then not exist. Yeah. And someone that is so instrumental in who you are you know i one thing i did kind of realize is that as you know this thing that that i'm doing for a living um one thing i realized is that when she was gone i i realized that part of the reason i was doing this in the first place was for her to see it yeah yeah you know yeah of course yeah and so when that was gone i was sort of like well who am i who am i gonna impress yeah you know yeah so i had to straighten that out and and and sort of come to terms with the fact that these feelings and this love that you have for a person and their love for you is you know doesn't go anywhere it's it's still it's still here it's kind of what you're made of yeah yeah yeah yeah like the structure of you is that's right and a parent dying is sort of a big it's like part of the sky going away or something.

1:00:01It's sort of a big thing. Well, it's the thing you're most tethered to. Yeah. So when my dad died, I had these conflicting feelings of like, A, he had become a dependent of mine. And so we were in this relation - You were taking care of him. Supporting him. Yeah. So unfortunately, a lot of our conversations over those last few years were like, I need this or it's just not a great dynamic. It's hard. Yeah. And then, you know, know, I lived with my mom primarily my whole life. And he, when he was dying, it was a lot of work for me. So I had this conflicting, I felt a sense of relief when he died.

1:00:37And I was like, okay, this battle's over. We got him through it without too much carnage. That's, that's a win. And so I think I had like, I had a misleading sense of relief for a few months and then opened up the door to like, Oh, I'm never going to chat with him again, or I'm never going to, he's not going to see anything I do you know but through all of that I was like also thank god it's not my mom yeah because my mom for me is the thing you're talking about like Dax wants to live in the woods and fucking be annihilated drunk all day and anything I've ever done positive was because my mom believed in enough yeah that I was a good boy yeah and I needed to make her happy yeah and so I've often thought like if she's not around for me to even think what would she think that That feels like a very scary place for me to be in.

1:01:27Yeah. I really rely on her to almost be my super ego. Yeah. Just like in the back of your head, your mom is this very unique station that. It's so fucking thankless. Like, do you watch Naomi and I watch Chris and I go, my God. Jesus Christ. And meanwhile, I'm walking around like, you know. And then they're like, dad. Yeah. I know. You know that Nick Kroll special where he's just like. Yes. Yes. Moms are annoying. Yes. And it's like, they are. Why? It's so unfair. Because they know you so well. Yep. That's right. In a way that no one else does. Not your dad. No one. They just know. They were in your body.

1:02:10Well, they're who you were able to be scared in front of, vulnerable. Yeah. Yeah. Oh, man. I mean, even as an adult, you know, something would happen. Yeah. I would call her and no matter how embarrassing, you know that that call is there. Yes. You know, to your point, guaranteed. I'm feeling better when I get off the phone with my mom. 100%. She'd somehow find the silver lining. That's right. Horrific. And give you the kernel of advice, whatever it is. Yeah. Stay tuned for more Armchair Expert, if you dare.

1:02:56From episode 864 with Mindy Kaling.

1:03:04So interesting. I worked in the office for eight years. Loved the experience. Largely male cast. What I want to write about is about women who are ambitious and lust after people that they're not interested in. Yes, yes. Is then every subsequent show, The Sex Lives with College Girls, this new Kate Hudson show, it's all just about women who are trying to make the most of what they have and have sex and be successful. The correlation from how I was in high school and what I didn't have is just expressed in those shows that I was able to do after The Office. But it's really interesting to me. My shows have a lot of horny women.

1:03:36And my friend BJ Novak makes this joke that every trailer for any Mindy Kaling show has a hot man's torso in slow motion. And I was like, how dare you? That's incredibly reductive. That's not true. And then it is true. Yeah. Every trailer. It's great. It's your turn. It's like Pauline Chalamet, Kate Hudson, Maitri Ramakrishnan, their head is turning. And it's just like those 80s movies that they can't make anymore. The National Lampoon movies where it's like a guy is following a bouncing girl on the volleyball team. And running point, she enters the coach's domain and he happens to be shirtless doing pull-ups.

1:04:10I do a lot of pull-ups, almost never shirtless. I mean, that's a good point. You can give it a try. It's a solid point. Might be better. It was Jay Ellis. So Jay Ellis on your show and he's like, could I wear my sweatshirt for my pull-ups? You'd be like, whatever makes you comfortable, Jay. But if it's all the same to you for the story. It's like having Jordan there and there's two sports on the table. You could either film him playing ice hockey or play basketball. We should have him probably play basketball. We should have him play basketball. Yeah, we should get that top off and see how many pull-ups we can do.

1:04:40And for the record, J. Ellis, he is a very funny part in this. He's more than just as hot by. But for the trailer. Yeah, you got it. You got to hook him. I'm still thinking about when Dax called me hot at the beginning. Yeah, you're very hot. I follow you on Instagram and I often look at pictures of you and I go, she's so hot. That's like really nice. I've told Monica that. I'm not doing this for your sake. This is a new information. Well, that's the outcome you hope for when you post those photos. Of course. And you think, oh, the best, some anonymous pervert in the middle of the country thinks that.

1:05:07But to think a celebrity is thinking you're hot. That's pretty good. I would guess many. In fact, most people think that. Hey, that's new. And that feels nice. Thank you. OK, so you liked boys. But did you not have a boyfriend through high school? No, not even through college. Now, this is really personal. But we just talked about mine. And I got to bring you into it, Monica. Sure. It becomes a point when I met Monica, she was 27, eight. Yeah. And as she was approaching 30, I just started getting the sense maybe Monica hadn't. I probably told you. Well, I asked you ultimately. I said to Kristen, I don't think Monica has been with a dude.

1:05:42And she's like, yeah, I think she has. And I'm like, I don't think so. And then I needed resolution to that kind of argument. Professionally, you needed to. Well, luckily, she didn't work for me. That's true. At the time. We were just friends. We argued about podcasts all the time. She hadn't. And then my first thought was, is it a religious thing? Right. I'm waiting for marriage. Yeah. I was like, do you want to be married? Is it a religious thing? You kind of want to say yes. There was a part of me that wanted to say, yeah, there's a real reason that I haven't. And there's a reason nobody wants to have sex with me.

1:06:15It's because I'm waiting for marriage. But no, I was just like, no, it's just hasn't happened. But then it becomes a thing, as Monica explained to me, where it's like now you pass some point where you're like, oh, my God, people are going to think this is weird about me. Were you starting to have any of those fears? Yeah. We're describing the premise of The 40-Year-Old Virgin, my first movie, which is good to hear that besides being just a funny comedy or like speaking to a truth. In my mind, I said this has to happen before I'm 24. And I don't know whether I heard this afterwards or not, but I remember one of the great gifts that Tina Fey, I think, has given to us, besides just being really funny and I love 30 Rock and just being such an amazing joke writer, is I think at some point, and she's not someone who is super open, but she said in a book or something that she lost her virginity at age 24.

1:07:01And I remember thinking, that's like a very nice thing to do. It's a gift. To give some guideposts to nerdy women. She's beautiful, smart, happy marriage, beautiful daughters. And I thought that was great because we can't all be Dax. We can't all be 12 and fucking. Well, hold on, guys. Don't make me the enemy. No, no, no. I was in a hick town and I was super large and we were bored. No, no, no. And I feel like I keep making you feel self-conscious about it. But so I remember thinking that then it happened before then. Good for you. You're way ahead of me. Did you? Monty had this too. There is an ambition.

1:07:34So if you do decide you're going to do something, anything in the world, you will figure out how to do it. That's true. And I think you pretty much were like, I'm doing this. It was like a ticking clock at one point. I was like, it really is time. I wasn't like, I don't care who. Doesn't have to be the love of your life. That was similar to how I felt. I didn't need that, but I didn't want to have a random hookup. And then I was never in a relationship. So I was like, how am I going to do it? So one thing I think that's tricky about Indian culture is this idea that in my house, dating or any of that was pretty much forbidden.

1:08:07In high school, no one is dating. By the way, not that anyone was coming after me or anything, but I also knew that it was not an option. And then you're expected to sort of like go to college and then meet someone and know how to date and then fall in love and get married. But with what skills? And everyone's already had five girlfriends that you're going to meet. I've not yet kissed somebody. Right, exactly. Or even know how to be normal in romantic, intimate situations. Forget even about sexual situations. Situations when someone wants to go to the movies with you and you're like, I only know how to do this with my female friend.

1:08:38Yeah. Like, I know how to go to the movie with my cousin. Yeah, what do I eat when I'm with you? Am I getting the popcorn and the milk duds? You've seen this probably people go into, I think I just need to have sex right now. Right. And so I didn't go through that, but now that I have three children, definitely want to de-stigmatize this. You know, I do feel pretty Indian and Hindu in a lot of ways, and I really want to instill that in my kids culturally. But I do think what I want for them is to be like, yeah, you can go on a date or you can like somebody and talk to me about it. Because I didn't love going into college being like, does a kiss with someone then mean we have to then take this all the way to its completion?

1:09:16Yeah. I didn't love that. It's also a source of a lot of my comedic storytelling. Never Have I Ever is literally about a nerd who asks the hottest guy at school, would you have sex with me? Growing up in the 80s and the 90s, and I think Dax were about the same age. Four years older than you, but thank you. Yes, yes, yes. 75. Sorry. You go ahead and say sorry. Sorry. Sorry. Sorry for your age. So sorry. I turned the age. Are you 50? I just turned 50 in January. Thank you. That's a good one. I made it. So in the 80s and 90s, it felt like there was so many coming of age for this like very specific kind of guy.

1:09:51A geeky guy. Can't buy me love. And then later, Judd did it with Superbad. And this is why I always feel like it's crazy when people can't watch things with subtitles. Because I'm like, my entire life was being able to relate to characters who look nothing like me. I can do it easily. I'm very invested in Ross and Rachel. And we were on a break. And like, I can relate to them. And so it's crazy when people are like, I can't watch Parasite. What if they're dyslexic? First of all, I loved Parasite. But what if reading takes so much of your concentration, you're totally missing all the visuals? That's a separate situation.

1:10:22And sometimes I find subtitles annoying, too, when I just want to relax. So I felt like that felt really untapped and fun. This thing that I could relate to and wanting to do shows and TV about that kind of stuff. From episode 954 with Charlie Sheen.

1:10:43Will you tell her about the time that you're visibly falling asleep on camera? Oh, yeah. No, that was, I don't know where that came from. I don't know. I think I do. I think it came probably from, you know, some sexual behavior that I'd heard about. Okay. But I'd never done it. Okay. She's like, what the hell? No, I want to know. What are we on the doorstep of? I was filming a movie in Canada called Free Money. And I've been going way too hard. And it was like midday and I had this scene in a cafe or a diner, right? Yeah. And I was trying to get through it and I kept the dialogue just, you know, some days it's just, it's in a different language, right?

1:11:27Mm-hmm. But it wasn't so much about the dialogue. It was about the level of fatigue. And I thought I was keeping it together, you know? And the director, between takes, he walks up and he says, hey, man, I see you falling asleep on camera. Oh, my God. Monica, in the take. Yeah, and I've never done heroin, right? Right. And that's like a heroin thing, right? Sure, nodding off. Boom, whoa. Or even Suboxone. Yeah. Right? Yeah. Which is like, you know, contemporary methadone. Yes, yes. I'm telling her. She's your co-host. No, she doesn't know. She doesn't know about Suboxone. No, I do. I've seen all these drug documentaries.

1:12:01I know about them. And over-prescribed everywhere on planet Earth and needs a closer look at that shit. Yeah, yeah. And so I said, okay, shit, all right, my bad. I need a cup of ice. Bring me a cup of ice. He's like, okay, what do you want to drink? I'm like, just the ice. And he's like, okay. I said, give me a minute. So I go into the bathroom. I'm like, okay, I heard about this somewhere else, but for sexual reasons, I'm gonna stick an ice cube up my butt No! Yeah, and I'm pretty sure and it was a good size one I didn't want it to melt What if you got one of those big round ones they make for whiskey?

1:12:43Can you imagine? If I see it in the cup, I'm like, no, no, no I need a racquetball sized piece of ice Can you imagine? Yeah, and I keistered it like I was sneaking drugs into prison, right? And freaking and was suddenly wide awake because it was so uncomfortable It was so cold. Not to mention the clenching you were probably doing to keep it in. Yeah, also the leaking. Yeah, you're just leaking. You're now peeing. Right, but I think I was in like a conductor's jumpsuit. You know, the overall thing? Yeah, thank God. It tells you the quality of the movie, right? And I came back to set, and I'm like, let's do this.

1:13:21You're so aware. Let's do this, man. Monica, there's footage of these takes in the movie, which is incredible. Yeah, and then I've got sort of the melty clock going, right? Like, how many takes is he going to need, right? And we got through it. And I think after that, I wasn't like, oh, I better go get the ice cube out. Sure. Because we've all, you know, thought about, like, the perfect crime. You know, you shoot somebody with an ice cube. Oh, yeah, yeah, yeah. Bullet. That's right. And then there's no ballistics, right? So I'm like, okay, it's just going to vanish. There will be no ballistics in this crime scene, right?

1:13:55And so we made the day. But when I saw that scene in the doc, I'm like, why didn't they just send me home? Right. Exactly. That guy's not well. Yeah. That guy's not well. You know, Dad and I go down to take part in a TV show that pits actors against athletes. And the card we drew was Michael Jordan. So it's a two-on-one versus Jordan. It's a three-part competition. It's free throws, a game of horse, and then a two-on-one. Oh, no. Wait till you hear how it plays out, Monica. I mean, do you want to know or do you just want to watch it? No, I want to know. I want to know this. He loves Jordan. I do.

1:14:35We beat him. How is this? No, no, no, no, no. Not only did he. How is this possible? Not only did he beat him. This is where he has these absolute, like, mythical strokes of magic. Yeah. He hit eight. Charlie hit eight free throws in a row. Did you play basketball? No, I played baseball. But I shot with dad in the backyard like my whole life growing up. Hit an 18-foot jumper in the two-on-two. To seal it. To win the game. To seal it, yeah. This is not a normal life. It's nuts. He gets out of treatment. He is dead. He's dead. One of his times getting out of treatment, dad picks him up. He wants to just watch baseball.

1:15:15He loves baseball. They stop by this place, and there's grown men playing a game of baseball in a league. And because they're them, all of a sudden they let Charlie take a nap back. Yeah. First swing, out of treatment, life's over, home run. Of course you're confused. Exactly. Of course you're confused. You've got like superpowers and then you're superhuman all the time. I mean, you're extra human and you have superpowers. This is too much to like be holding all at once. That's a lot. But on the drive back from the Jordan thing, I've got the scene with me. Uh-huh. Because I know that like on Tuesday or maybe even Monday, I have to report back and do this thing.

1:15:53Yes. And so I read it with dad in the limo, just having done the Jordan thing, working on Bueller, right? And we read it once. I didn't do anything with it. And he stopped me and said, that's it. You've nailed it. And I was confused. I was like, I did nothing. And he said, it took me 30 years to learn how not to do that. Yeah, it was a trip. Wow. So that's kind of what I walked in with. and I was really hoping that Hughes was going to be okay with this giant, you know, very specific piece of advice. Yeah. You know, and he was. Yeah. And he was. But of course, on the day I overslept and I was two hours late and it was like.

1:16:33Really? Oh, wow. Yeah, it was awful. He gets the job. I mean, he gets the job. Wow. This is, again, this is an easy theory to make and I want you to tell me if you think there's anything realistic to this, which is these things come incredibly easy to you and something about the subconscious goes, this isn't right. Yeah. And we're going to fix it. And the way we fix it is we're going to destroy it. Right. Sure. Some self-sabotage. But this was, I think, before. Oh, yeah. Yeah. But there's an inkling of it. It's like, how are you on time to get the job? You get the job too easy. You go win a game with Jordan.

1:17:07Somehow you can't fucking wake up on time. That's a good point. Why can't you wake up on time? You make a good point. You weren't late for the thing. Yeah, that's true. You weren't late for that. Yeah. You know you got that too easy. And now we're like, you have a reason, but it's suspicious. Yeah, it is suspicious. Even sitting here today. It doesn't make sense. Yeah. And a lot of your stuff doesn't make sense. You can't draw it up. Right. You can't plan it, you know?

1:17:46follow armchair expert on the wondery app amazon music or wherever you get your podcasts you can listen to every episode of armchair expert early and ad free right now by joining wondery plus in the wondery app or on apple podcasts before you go tell us about yourself by completing a short survey at wondery.com slash survey Okay.

From the publisher

On this special episode, we revisit some of our favorite moments from Monday episodes in 2025. Nikki Glaser relays the risks of a roast, Brad Pitt commits a non-union extra faux pas, Dominic Fike drops his mixtape in jail, Dove Cameron tries to mend her relationship with her dad, Alexander Skarsgård finds his way as an actor post-Zoolander, Jennifer Aniston talks kids and SNL, Adam Scott discovers grief for his mom while filming Severance, Mindy Kaling writes nerdy women who desire, and Charlie Sheen keisters an ice cube after falling asleep on camera.

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