Tom Green: A call from Diddy, drinks with Rodman, reunion with Trump | Trending Now

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0:48It's Graham. And today we're going into the archives to bring you one of the most popular clips on our YouTube channel ever. The clip you're about to hear is trending on our Instagram right now. Hope you enjoy. This week, Tom Green.

1:04So I want to run through some of kind of the notable folks that you've crossed paths with over the years. The first Letterman appearance and what comes to mind there, because obviously I think Dave was somebody you used to dress up as back in the day. Yeah. How do you dress up as Dave Letterman? You know, khaki pants, Adidas shoes, and a blazer and a tie. And I would do stand-up comedy sort of dressed in that way when I was a kid. And probably even mimicking his sort of cadence and his delivery a bit, you know. You know, I would host the school talent show with, you know, a musician from the school who had a Hammond organ with a Leslie amp.

1:50And he'd be Paul Schaefer and I'd be Letterman. We put a desk on the stage and I would do a little talk show and introduce all the bands and stuff at the school. So, yeah, I loved Letterman and grew up. And my documentary that's on Prime covers that and follows me into my sort of whole sort of lifelong sort of admiration of David Letterman and me eventually getting to go on a show. But it was surreal. And hosting the show, too. Yeah, a few years later. It was surreal because MTV was just sort of realizing that the show was a hit. And then all of a sudden Letterman called and it was just sort of put it over the edge.

2:26That's one thing that happened with the Tom Green show, right? It's this little thing that they picked up from Canada. We threw it on the air and then within weeks, Todd Phillips and Pepsi called. And I'm doing the commercials. They ran during the NCAA tournament. you know, basketball, college basketball, which popped the awareness of me. And then Letterman called. And, you know, MTV was just kind of like, what the hell? This is just supposed to be some goofy little show we're putting on. And now all of a sudden Letterman, you know, in New York, everybody, everyone loved Letterman, but in New York, he was just the king of New York, right?

3:06So people were just kind of, you know, my bosses at MTV were starting to realize, oh, this show is important. He's doing Letterman. That's cool. So that was amazing. I remember standing in the side of the stage and Biff Henderson comes out. He's actually the floor director of the show. And I'm like, I'm about to go on. And Letterman's over at the desk. And I somehow mustered up the nerve to wave at him before I went on. And he looked over, hey. And I was like, oh my God, Letterman just looked at me. And then I walked out and did the show and it was awesome. Couldn't believe it. But yeah, it was cool.

3:40That was one of those things that you just can't believe. At the time, just could not believe that was happening. All right, here's somebody who's in the news right now for all the wrong reasons. You get a call from the office of Puff Daddy. Yeah, yeah, yeah, that's right, yeah. What stands out from that? When the show first got picked up by MTV and we were on the air, we got a call from Puff Daddy to come, and he wanted to meet me. so I went over to Bad Boy Entertainment to his recording studio and me and one of the writers of the show and I went over there and he sort of played some of his music.

4:23And, you know, I'd been in a rap group when I was a teenager so I was kind of pretty excited. But, you know, I mean, you know, I don't even want to smile talking about the story and we're sort of like you can't even really talk about it anymore in a way. in the new context of what's going on, it's, it's, it's, it's, it's, uh, I mean, it's a different story now. It's a different story now. Like I can, oh my God, it was so amazing, you know, but it's like what's going on now. You sort of don't know what to think about what's, what's happening. But, uh, but at the time, you know, um, I sometimes think like I was a little bit, uh, naive to the way show business works, you know, like a lot of, a lot of show business about relationships and all this type of thing.

5:08And I didn't really realize that. And I was so driven to shoot the show. We went over to the studio and at the end of the visit there, he said, I'm having a party this weekend. I want you to come to the party. And he gave us a couple of passes to this party in the Hamptons, right? And I went back to the office and the party was like on the day we were supposed to go shoot some goofy bit on the street. And I just sort of said, Well, we can't go to Puffy's party. We got to go make our bit on the street. We got to go film our funny bit. So then one of the producers or something went to the party, and it was just like him and his kids and four people there hanging out at his house, and the producer showed up at the pass thinking it was going to be some big party.

5:53And anyway, so I always thought, at the time, I always thought, oh, boy, I probably should have gone to that party. But I was too busy, like, you know, delivering a fake pizza to somebody and getting chased by a guy with a hammer in Long Island, you know. So good, so good, so good. Spring styles are at Nordstrom Rack stores now, and they're up to 60 percent off. Stock up and save on Rag & Bone, Madewell, Vince, All Saints, and more of your favorites. How did I not know Rack has Adidas? Why do we rock? For the hottest deals. Just so many good brands. Join the Nordy Club to unlock exclusive discounts, shop new arrivals first, and more.

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7:08How about the connectivity between you and Eminem? Yeah, that was cool too. I mean, that was crazy. Like when the Bum Bum song came out, which was my song, we set out to make the stupidest song ever. I think we accomplished that. We put it on the show. It went to number one on Total Request Live. Got you a record deal. Got me a record deal, yeah. Which that record didn't come out because of my cancer. But I did get a big record deal with Virgin Records. But can you imagine an entire record of bum-bum songs? I mean, what we missed out upon on there as a society, I think, is just horrible. You had the number one song on the planet.

7:51Yeah, yeah. It was crazy. And then Eminem's next single was him dressed up as me in the bum-bum song, Slim Shady. If you watch that video, he's running around with a superhero costume on, the same exact superhero costume. And he raps about me humping a dead moose. Unbelievable. President Trump, what stands out from your experience with him on The Apprentice? You're talking about Dennis Rodman? No, you're talking about Donald Trump. I'll ask you about it after that. Rodman's awesome. We had fun. I probably got fired because of how much fun I was having hanging out with Dennis Rodman. We would go out drinking on the nights we were supposed to be working and stuff.

8:36It was pretty fun. If you get to go drinking in New York City with Dennis Rodman, don't pass that up. That's a lot of fun. He knows how to have a good time, that guy. Best person you've ever partied with? I mean, in terms of, like, most fun you've ever had? Well, we were in New York, and he's Dennis Rodman, and he's... First of all, you walk in a room, and everybody immediately sees this Dennis Rodman. But, no, he's a fun guy. Yeah, a fun guy to hang out with, yeah, for sure. But, yeah, Donald Trump was, you know, it's true I was on The Celebrity Apprentice. That's true I got to hang out with the president of the United States.

9:21But, unfortunately, I went out drinking with Dennis Rodman, and I screwed the whole thing up. So I got fired. But you got back. And then he brought me back, yes. I wrote a letter to Donald Trump after I got fired on Trump Tower stationary. We were staying in Trump Tower. I wrote a letter. I said, Mr. Trump, you know, I'm a comedian. And I know I got fired because I went out drinking with Dennis. But honestly, I thought it would be funny for the show. And I wish you all the best with the show. I just wanted the show to be funny. And thanks for having me on kind of thing. But completely genuine.

9:57Genuine, yeah. Absolutely genuine. And when the next day I got a call from the producers and they wanted to bring me back, so they brought me back for the final challenge. So I have the distinction of being, you know, they always bring people back for the final episodes who were fired, but they bring like two people back or something. Yeah. But I have the distinction of being the earliest person to have been fired to get brought back. They usually bring someone that stayed on to like episode seven and then got fired. They bring them back. I got fired episode three, so. I mean, that is cool, though.

10:24It's pretty cool, yeah. Yeah. It's a pretty cool thing. All right. And lastly, your most memorable interaction from having William Shatner as your landlord. Yeah. So when I moved to Los Angeles, I rented a house to live in and it happened to be the William Shatner owned the house in his neighborhood that he rented out. And he was my landlord. And well, a couple of things. I've had a few. He's Canadian. So it was very exciting to meet this Canadian icon who I grew up watching on Star Trek, and now he's my landlord, literally would come over to pick up the check from me once a month, like a couple of times.

11:04He would just look, come over, here you go, and paying my rent to Captain Kirk here. But then he actually came in and met with me to play my father in Freddy Got Fingered. and I met with William Shatner, James Woods, John Voight and Rip Torn. And, you know, truth be told, I mean, we had written the movie with William Shatner in mind, actually. And so this was somebody we really wanted. And then the studio really, really wanted me to use Rip Torn. and I was like, well, that'll be awesome too. But I do also remember one day I was sitting in front of my rental house still, in my rental house, and I just found out that we were going with Rip Torn and my landlord pulls up and his Jaguar and I'm standing there and the window goes down and he goes, so what's going on with the movie?

12:03I go, oh, yeah, actually, studio wants to give it to Rip Torn. He said, okay, boom, drives off. It's like, really? Yeah, that was my last interaction with my, No, I used to see him around town, too. I don't think there was any hard feelings. As always, thanks for listening. To see more trending clips from my team, go to youtube.com slash Graham Bensinger.

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