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Blocks w/ Neal Brennan

Tom Green

Thu, 15 May 2025

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Neal Brennan interviews Tom Green (The Tom Green Show, Freddy Got Fingered, This Is The Tom Green Documentary) about the things that make him feel lonely, isolated, and like something's wrong - and how he is persevering despite these blocks.  ---------------------------------------------------------- 00:00 Intro 00:33 Testicular Cancer 3:44 White Rapper 4:59 DIY roots 6:18 Norm Macdonald & Letterman 9:44 Experiencing sudden fame 15:05 Hosting SNL 19:08 Sponsor: Harrys 21:10 Sponsor: BetterHelp 23:13 Early adoption of creative technology 26:45 Negative reaction to fame 30:05 Shell shocked by fame 32:10 Downside of sudden fame 35:45 Relationship with Drew Barrymore 37:07 Anxiety 41:16 Testicular cancer 48:41 Difficulty of public relationship 51:39 Sponsor: RocketMoney 53:10 Moving back to Canada 1:03:29 Positive Thoughts 1:06:30 Procrastination & Indecision 1:15:26 Keeping the Dream Alive 1:17:05 How His Relationship with Himself has changed ---------------------------------------------------------- Follow Neal Brennan: https://www.instagram.com/nealbrennan https://twitter.com/nealbrennan https://www.tiktok.com/@mrnealbrennan Watch Neal Brennan: Crazy Good on Netflix: https://www.netflix.com/title/81728557 Watch Neal Brennan: Blocks on Netflix: https://www.netflix.com/title/81036234 Theme music by Electric Guest (unreleased). Edited by Will Hagle ([email protected])  Sponsors: An exclusive offer for our listeners -- Get a $10 trial set for just $5 at https://www.harrys.com/NEAL  This episode is sponsored by BetterHelp. Give online therapy a try at https://www.betterhelp.com/neal and get on your way to being your best self. Cancel your unwanted subscriptions and reach your financial goals faster with Rocket Money. Go to https://www.RocketMoney.com/NEAL today. Sponsor Blocks: https://public.liveread.io/media-kit/blocks ---------------------------------------------------------- #podcast #comedy #mentalhealth #standup Learn more about your ad choices. Visit megaphone.fm/adchoices

Audio
Transcription

Chapter 1: What is Tom Green's experience with testicular cancer?

0.149 - 16.108 Neal Brennan

hi guys it's neil brennan on the blocks podcast my guest today um he's got one testicle so right there get right into it yeah right there uh he was host of the tom green show freddie got fingered road trip where they confused austin and boston

0

16.468 - 19.709 Unidentified Speaker 1

Austin, Massachusetts. You mean Boston, Massachusetts?

0

20.269 - 32.413 Neal Brennan

That was a big plot twist. Absolutely. Yeah. And now he's got a farm. He's got a he's got a document on Amazon, which I watched not knowing he was coming. And it's very exciting. Tom Green is here. Tom Green. Tom Green.

0

32.593 - 47.742 Tom Green

Awesome. Awesome. I do have one testicle. Yeah. Well, I lost my testicle in 19 what it was 2000. You think I'd remember the year. Yeah, I was doing my show on MTV and we filmed it all. We filmed the whole ordeal. But I still have the left one, so everything's fine.

0

47.982 - 51.545 Neal Brennan

That must have been so surreal. You must have been like, what?

51.925 - 53.987 Tom Green

Yeah, it was kind of a curveball for sure.

55.888 - 69.88 Neal Brennan

That was one of those, the most recent one in culture was like Luka Doncic got traded from Dallas to the Lakers, right? The big sports thing. But it was that big a plot twist where it was like, what? What?

70.16 - 83.591 Tom Green

Yeah. Yeah, it wasn't good timing for sure. I mean, it's never good timing to get testicular cancer, but it was particularly bad because the show had just come on MTV and things were going good for me. You were cresting.

83.611 - 106.813 Neal Brennan

You were crowning. You were like ascendant. And you were also rare in that you were under 30, right? Yeah, 28. Yeah. And nobody was really young in show. Like there was like the pop stars, but but you seem especially young back then.

Chapter 2: How did Tom Green's early career in white rap influence his creativity?

224.706 - 235.254 Neal Brennan

There was a lot of stuff in the documentary that I was surprised by or that I guess I just didn't know. One of them was that you were a white rapper. Yes, yes, yes, yeah.

0

235.574 - 235.674 Tom Green

Yeah.

0

239.867 - 251.935 Neal Brennan

Tom Green was a successful white rapper, about as successful as white rappers can. I mean, they only let in about one every five years. It seems like it would be an epidemic, but it's about one every five years.

0

251.996 - 255.498 Tom Green

Back in 1992, it was the Beastie Boys and Vanilla Ice.

0

255.738 - 258.74 Neal Brennan

Yep. That was from 1988. Third base.

259.1 - 287.644 Tom Green

Third base, of course. They were great. But, you know, we were kind of... Definitely loved hip-hop music. I did a radio show at the college station when I was in high school. I'd go down and do a rap music show. I made beats. That was kind of how I got into technology and video and everything was through the rap group Organized Rhyme. I'd work my summer job. I'd save up. I'd get a sampler.

Chapter 3: What were Tom Green's DIY roots and how did he get started in entertainment?

288.124 - 290.865 Tom Green

And then we just started sampling records and wrapping them.

0

290.885 - 307.809 Neal Brennan

Was Organized Rhyme spelled correctly? It was actually spelled correctly. Very Canadian of us. Okay. And yeah, that was another thing I liked about the documentary was how DIY your whole thing was.

0

308.382 - 332.378 Neal Brennan

Like it really was, you went, because we're around the same age, like you had to go rent a camera from either your school or whatever and then make a thing and put it out and see if people liked it and it's hard to root against. Do you know what I mean? Like once you know that, you just go, oh, well this guy, He did it the right way.

0

332.418 - 349.008 Neal Brennan

Like, he ran for local office, and he won, and then he ran for national office, and he won, and then he ran. And even the wind-up to MTV was long. Yeah, yeah. It seemed, to my eye, it was like, oh, who's this guy? You know what I mean?

0

349.028 - 371.348 Tom Green

Yeah, I think that probably a lot of people felt that way because it was – I mean, doing it in Canada for – probably 10 years, really, you know, if you include the rap group, right? And then, you know, obviously MTV is such a... Especially then was such a... You know, you get on MTV, and they were playing the show five times a day. It was sort of thrown right into American culture.

371.368 - 391.986 Tom Green

It was a real whirlwind. But yeah, it was... It was exciting. I did stand up when I was a kid. When I was 16, I started doing it. And I stopped when the rap group got the record deal. I was about 19. We stopped at Yuck Yucks in Ottawa, where the same club where Norm Macdonald started.

Chapter 4: How did Tom Green's relationship with Norm Macdonald and Letterman shape his comedy?

392.086 - 397.511 Unidentified Speaker 2

I always thought that was the weirdest gift to give somebody, a lottery ticket. Here you go. Nothing. Nothing.

0

399.278 - 400.959 Neal Brennan

It's a chain in Canada. It's a big chain, yeah.

0

400.979 - 419.549 Tom Green

It's sort of like the improv of Canada. And Howard Wagman is a manager there, still runs the place. He's Mark Breslin's nephew who runs the whole club. But, you know, I was just a kid doing it. And it sort of – because I'd go down there to see Norm. I'd go down there. Because he had not come to the States yet.

0

419.589 - 427.273 Neal Brennan

And that was sort of a moment where I realized – Was he – was Norm doing especially well in Canada? Was it a bit of a word of mouth thing? He was the headliner in Canada.

0

427.313 - 428.294 Tom Green

He hadn't moved to –

428.874 - 432.957 Neal Brennan

And there probably were, I guess there were a number of headlines in Canada, right?

433.157 - 451.229 Tom Green

Yeah, there were Canadian comics that would sort of, you know, before they, you know, if they moved down to the States back then, they would just sort of tour the Yuck Yucks chain. And so Norm was kind of at the top of that group. And then shortly after I discovered him, he moved down to L.A. and started working as a writer on Roseanne, I think so.

451.809 - 463.176 Tom Green

But, you know, I remember when that happened, when he went to Roseanne and then Saturday Night Live, and I was just like, wow, he was just here in this little dark basement a few months ago.

Chapter 5: What was it like for Tom Green to experience sudden fame on MTV and beyond?

463.236 - 466.058 Neal Brennan

Was it the same kind of jokes, like obtuse and weird?

0

466.118 - 479.224 Tom Green

Yeah, that was sort of the thing. It was sort of the first time you're really going out to see comedy in a live venue. You're 16 years old. You're just kind of excited to be in a bar.

0

479.244 - 484.647 Neal Brennan

That's one of those luck things, and it turns out to be one of the best comedians ever.

0

484.867 - 511.919 Tom Green

yeah and then he's and it was just he was you know he was in his 20s you know yeah and it was just mind-blowing yeah you know because uh because obviously there was was weird comedy back then but he was sort of one of the ones that really stood out that i saw live that was sort of more out of the box than a lot of the more sort of straight straight edge kind of comedy that was going on at the time yeah he had like great tastes and great instincts and like not a hacky bonus but just had like

0

512.839 - 515.5 Neal Brennan

knew, he had like ethics.

515.86 - 541.607 Tom Green

Yeah, yeah. And just shocking. I wish I could remember some of the bits he did back then, but it was just, it was that sort of idea that you can just sort of turn the whole idea of stand-up sort of upside down and do it differently and kind of confuse and shock everybody, which was kind of amazing to me. And, yeah, but, you know, it's hard doing stand up when you're 16 years old and 17 years old.

541.647 - 542.427 Tom Green

It really was never.

542.447 - 553.691 Neal Brennan

People don't like you to talk about certain. I remember Chappelle started when he was 14 and he did sex jokes and somebody told him, like, you can't do sex like people don't want that from a 14 year old.

553.971 - 571.281 Tom Green

Yeah. And for me, it was just the confidence. I was terrified, you know. Yeah. And you're performing to a bunch of college kids, you know, and you just didn't have that kind of confidence to, or life experience or anything to really add. So it was more of silly, you know.

Chapter 6: How did Tom Green handle hosting Saturday Night Live and his fears of failure?

678.627 - 707.143 Tom Green

Yeah, well, okay, that makes it easier. Look, you have to have a certain amount of unbridled, even if it's misplaced, confidence to be able to just have the gall to decide to do that. Like, we're going to go paint my parents' car and film it and expect somebody's going to think that's interesting. And just the amount of work that we put into filming it every day, it sort of slowly built its...

0

708.561 - 711.862 Tom Green

following on the public access station in Canada.

0

711.882 - 713.783 Neal Brennan

But even that was slow, according to the documentary.

0

713.823 - 741.449 Tom Green

Yeah, it was a few years, and I did the show for probably four years without making money doing it. Then we got picked up by the Comedy Network the year before MTV picked it up, which was a little new cable network. But we sort of had this sort of... I guess I'd say sort of a skateboarder mentality. I watched all the Bones Brigade, Stacy Peralta, Future Primitive, Animal Chin.

0

741.93 - 761.331 Tom Green

You know, the idea of watching them go just, you know, cruise down the street on their skateboards and cause chaos. It was the first time I'd ever seen that, you know, because there hadn't really been video cameras before that. And all of a sudden you're sort of seeing a professionally produced video, but it's not totally professionally produced. It doesn't totally look like what you see.

761.351 - 775.26 Neal Brennan

There's something amateurish about it. Yeah. Because they weren't professional actors. Yeah, yeah. And I would also like to mention the Beastie Boys being part of that. Like they were early 90s, like homemade, DIY, fun, silly,

775.62 - 801.233 Tom Green

Yeah. And so when you're in that skateboard world, it brings you into listening to rap music too. You're listening to music that was made in a basement somewhere. There was a little bit of a feeling of, we're going to dismantle the way television gets made. A little bit of a youthful naivety kind of thing.

802.735 - 819.335 Tom Green

But then all of a sudden, I'm getting asked to go on The Tonight Show or Conan or Letterman. And Letterman was the first show that I went on that was... The first two shows as a talk show I went on was Oprah and Letterman.

819.495 - 828.702 Neal Brennan

And I was... Yeah, the Oprah one in the documentary. I was like, he did Oprah? Yeah, yeah. And he's my favorite. Like, she said something, like, very favorable, which I found funny.

Chapter 7: What are the psychological effects of fame and how did Tom Green cope with anxiety?

946.548 - 960.511 Tom Green

Just going on and being funny, you know, in a normal way. I thought, well, I can hide behind some outrageous sketch. Then another part of it was that also I loved watching Chris Elliott come out from under the stairs on Letterman and turn the whole show on the set.

0

960.531 - 965.036 Unidentified Speaker 2

Yeah. Chris Elliott. Chris, why don't you tell the folks a little bit more about this lovable character?

0

965.237 - 974.368 Unidentified Speaker 3

Well, sure, Dave. I think the character is kind of an extension of myself. Simply put, I live here underneath the bleachers, and I'll be interrupting the show from time to

0

974.83 - 1001.564 Neal Brennan

yeah uh i think it was like maybe sometimes i think in hindsight i think about this a lot actually i would think you do yeah man because it's really just gone the show was so nuts i probably should i remember when i and i my buddy mike sure was right in there he didn't i don't remember he would tell me generally when someone was being a pain in the ass i don't remember them saying anything yeah yeah have you has anyone said anything in retrospect or like

0

1002.152 - 1010.678 Tom Green

Uh, you know, a couple of times you hear he brought his own writers or something like that. And it's like, well, it wasn't really, it didn't really bring writers. It was more like one of my high school friends.

1010.718 - 1021.105 Neal Brennan

So did Ray Romano brought his own writers. They wrote that sweet, sassy, molassy sketch that ESPN, Dave brought me. You know, if you, if you have a thing, sometimes you're, they don't mind.

1021.553 - 1039.071 Tom Green

Yeah. OK, that's cool. That makes me feel better. Yeah. 20 years of anxiety over. I believe it. No, because like, you know, a lot of it was also just about wanting to bring your your friends with you who came up with me and and be part of the part of the SNL experience. But but, you know, I mean, it does definitely kind of.

1039.151 - 1061.481 Neal Brennan

But was it arrogance? I mean, that's these this sounds like fear. And even the thing of doing things your way. Anything original can sometimes be from a place of, like, I can't do it normal. I don't have that skill set. Like, I don't think Andy Kaufman would have been a good comic.

1061.721 - 1062.622 Unidentified Speaker 5

Mm-hmm, mm-hmm, mm-hmm.

Chapter 8: How did Tom Green's public relationship with Drew Barrymore impact his life?

1116.055 - 1138.788 Tom Green

But, you know, I think that what happens also is, or what happened to me was all of a sudden there was all these opportunities and they were opportunities that like, I felt like, I don't know how to do that, you know? And it's sort of like, well, maybe I'll pass on that. Not because... because I'm too good for it or whatever. It's more like I'm afraid of not pulling it off, you know? Yeah.

0

1139.129 - 1149.255 Tom Green

And so that may sometimes have come off as arrogance or something when really it was more probably fear-driven again, you know? So there's a lot of that.

0

1149.876 - 1176.117 Neal Brennan

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1176.417 - 1179.76 Neal Brennan

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1286.346 - 1306.96 Neal Brennan

And I ask people overly personal questions. But it works as a podcast. And by the way, we almost always mention therapy having helped them. Mental health awareness is growing, but there's still progress to be made. We've got a long way to go. 26% of Americans who participated in a recent survey said they have avoided seeking mental health support due to fear of judgment.

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