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Before YouTube, there was The Tom Green Show. It had the loose frame of a late-night talk show but what made The Tom Green Show stand out when MTV premiered it in 1999 were the videos Tom Green and his skateboarder friends had shot in their native Canada, pulling pranks like painting his parents’ house plaid or using a megaphone to harass unsuspecting pedestrians.
Almost instantly, Green became an unlikely megastar, gracing the cover of Rolling Stone, hosting Saturday Night Live and (briefly) marrying actress Drew Barrymore.
“My life changed, probably in a bigger way than you can ever really imagine someone’s life changing in a six month to a year period,” Green tells me on this week’s episode of The Last Laugh podcast. “I went from living in my parents’ basement to being very comfortable, let’s just put it that way.”
“I don’t think people really understand how hard I fought to get the crazy, absurd insanity of what I was doing on the air. Even after they picked up the show they didn’t want to put it on the air,” he adds. “But I’m a stubborn person and I was very protective of the comedy. And because I fought for it to get on the air in its purest form the show became a success and once it became a success that did open the door for other shows that came after it.”
Of course, Green’s fall was just as rapid as his rise. After he was diagnosed with testicular cancer at just 28 years old, MTV stopped production on the show. Once he was in remission, Green made a play for movie stardom.
First came the hits Road Trip and Charlie’s Angels, where he met Barrymore. Then there was Freddy Got Fingered, which he not only starred in but also wrote and directed. While Green says people still approach him nearly every day to quote lines from the film like, “Daddy, would you like some sausage,” it was a massive box office flop that more or less derailed his comedy career.
“I had multiple films that I could have done instead of Freddy Got Fingered,” Green reveals, including ones “that other people wrote, that major studios were coming to me with, that major stars ended up doing, that became huge movies.”
Green imagines an alternate universe where—instead of making one of the biggest bombs of all time—he starred in a string of wildly successful comedy hits. On the one hand, he says that “would have been pretty cool,” but on the other, he adds, “I don’t know if I would have been as satisfied creatively with what I was doing.”
Nearly two decades later, Green is a working stand-up comedian, touring the world “pretty much non-stop” and trying to stay relevant through bizarre stints on reality shows like Celebrity Big Brother and before that, The Celebrity Apprentice, on which he was fired by Donald Trump for staying out too late drinking with Dennis Rodman.
Earlier this year, Green finally became a U.S. citizen. “It’s nice knowing that I can’t get kicked out. It’s nice knowing that I can vote,” he says, before adding, “I don’t think it really had anything to do with my old boss.”
Highlights from our conversation are below and you can listen to the whole thing right now by subscribing to The Last Laugh on Apple Podcasts, the Himalaya app or wherever you listen to podcasts.
On ‘speaking truth to power’ on ‘The Tom Green Show’
“I still think there was an element of The Tom Green Show where we were speaking truth to power. As a 28 year old, I sort of felt like I was rebelling against authority and the status quo and the media and even the way comedy was made. Take something like hanging a painting on the wall of the National Art Gallery of Canada and seeing how long it would stay there. When you’re getting chased by a security guard, the ‘power’ for a 28-year-old skateboarder is the security guard. I felt like in some ways we were mocking television and even mocking comedy. And I think that may have potentially rubbed some people the wrong way, even in the comedy industry.”
Does he regret any of his ‘Tom Green Show’ pranks?
“Most of the bits, before we shot it, we would say what’s the requirement to go shoot this? And my friends and I would look at each other and say, well let’s think of something where in 20 years if someone asks you if you regret it you’ll say, yes I regret it—OK, let’s do that. Let’s think of something that will make us cringe. Let’s try to do something that’s the most embarrassing, ridiculous, crazy, strange thing possible. Because we went into with that mindset, there’s not really anything [that I regret]. I always felt like I had a moral and ethical line that I didn’t cross. I never wanted anybody to be ridiculed in a way that, if you take a step back and get out of the heat of the moment—I think anybody that appeared on camera, once they stepped back and realized what was going on, they weren’t really offended by it.”
How his cancer diagnosis altered the course of his career
“That’s why it ended. There are some misconceptions out there, because the show wasn’t canceled. I quit the show. Essentially I did the cancer special and that was the last episode of The Tom Green Show. People sometimes think it was canceled when they talk about it. I’ve tried to clarify that over the years, because it does matter to me that people know that the show wasn’t canceled. It’s kind of rare that a show goes out on top like that. So I had cancer, I had this massive surgery, removing lymph nodes out of the back of my spine and all this stuff and it was extremely painful. To be completely honest with you, I had major opportunities in film. I was being offered Stealing Harvard, Freddy Got Fingered, other movies that I didn’t do, Road Trip. There were huge opportunities for me, coupled with the fact that I could not see myself in that condition going out on the street and falling down on the ground and getting chased by people.”
Why he ‘actually liked’ Donald Trump on ‘The Celebrity Apprentice’
“It is surreal to say that you know the president of the United States. I can recall dozens of one-on-one conversations I had with him while we were filming. I do find it disappointing—and that’s the kindest way I can put it—the rhetoric that he has used, the racial division that he has used. That I find so upsetting. Because if it wasn’t for that—the divisive, racial tone that he has brought to the country—if it wasn’t for that, I would actually like him. It’s not like I have a problem with the way he’s aggressive on trade or the way he is with so many issues. That to me is upsetting, because I actually liked Donald Trump. The reason I did The Celebrity Apprentice is because I thought he was funny. Even when he screamed at me and fired me I liked him.”
Next week on The Last Laugh podcast: Stand-up comedian and star of ABC’s Black-ish and Grown-ish, Deon Cole.