From the late nineties into the early aughts, few comedians were as ubiquitous as Tom Green. With MTV’s The Tom Green Show, as well as roles in Road Trip and Charlie’s Angels—alongside then-partner Drew Barrymore, a relationship that piqued our collective curiosity—the slacker-provocateur rode a wave of charm and diablerie to the A-list. Green walked so Jackass could run.
Then Freddy Got Fingered happened.
The absurdist 2001 film, written, directed by and starring Green, was savaged by critics—CNN called it “quite simply the worst movie ever released by a major studio in Hollywood history”—and stopped his Hollywood career dead in its tracks. More hardships followed, including a highly-publicized divorce from Barrymore, and his late-night program The New Tom Green Show being canceled by MTV after just eleven weeks (despite positive reviews).
In the years since, Green has popped up as a correspondent on The Tonight Show, a contestant on The Celebrity Apprentice (where he was fired by Donald Trump during the third episode), and occasional film and TV cameos. But the 48-year-old Ottawa native’s experienced a resurgence of late, touring the country with his stand-up act and appearing in the wacky sci-fi comedy Iron Sky: The Coming Race, where he plays a demented cult leader who preaches the gospel of Steve Jobs.
What are you up to these days?
I’m in Ottawa fighting City Hall right now about their plan to renovate with a poorly-designed, modern addition to the legendary Canadian heritage hotel, the Château Laurier. So, it’s been an interesting vacation. I was home to visit my parents and ended up getting involved in some activism in my hometown. You know, I grew up skateboarding downtown and around this area. It’s a beautiful, pristine city, and I want to make sure they don’t do anything to ruin it.
And I saw that you became a U.S. citizen earlier this year, so…congratulations? Or are you a bit conflicted about that given the state of things in America?
I’m not conflicted! I’m still Canadian as well—a dual-citizen. I love the USA. I’ve been living in Los Angeles for twenty years, and MTV changed my life. They picked up my show from some obscure station in Canada and put me on TV all around the world, which has afforded me the ability to travel the world, do stand-up, and live my dream. I was on a green card for 15 years, I’ve been to every state in the United States, and I’d like to be able to vote. So, I’m looking forward to be able to do that.
So you became a citizen to vote in the 2020 presidential election.
Absolutely. That’s the reason I did it. I’ve been living here for a while, felt like I’ve contributed in my own way and worked with a lot of amazing Americans. I love the country, and feel like I want to take part in the political process.
Was part of the motivation to vote against Trump?
I don’t really want to talk politics, but yes, you can make that assumption. You know, I know Donald Trump. Donald Trump fired me on The Celebrity Apprentice. So yeah, I know the president. It’s…interesting. But we’re living in interesting times.
On Celebrity Apprentice you got to experience Trump up close in a way few of us have. What did you think of him?
I had several brief interactions with him off-camera, so it wasn’t just what you saw on TV. It was an interesting situation, because he was someone who had the power to fire you—that was the game, so there was this dynamic of power there. We would talk in the hallway between shots and he was always cordial but a very serious guy. He wasn’t a guy you would goof around with; he was an intense personality. I was very into doing that show because, before Donald Trump was the president, his actions didn’t have the same kind of consequences. I found it funny to watch him on television, and I loved the comedy of The Apprentice.
The cast of Season 2 of The Celebrity Apprentice
NBCAnd you went out in a blaze of glory.
Right! I got fired because I went out drinking with Dennis Rodman on the night I was a project manager. It was a decision that was made logically. My team of celebrities had essentially mutinied against me and refused to do their jobs in the competition that week, so I knew I was going to lose the competition and as the project manager would be fired, so I thought it would be more fun to end the show that way. And it was.
And now he’s president.
You know, after the show ended and I was fired by Trump, the president of the United States, I wrote him a letter on Trump Tower stationary, where we were staying, and I said, “Mr. Trump, I know I went out drinking with Dennis Rodman and that may not have been the most businesslike thing to do when I was a project manager. But I want you to know that I’m a big fan of the show, and as a comedian, it felt important to me to do something that would be entertaining. And I wish you luck with the show.” The next day, I got a call from the producers and they said, “Mr. Trump really liked your letter.” I think he understood that the reason I got fired is the same way he’s sort of lived his life: by being inappropriate in a way that can gather some attention. And another weird thing was, I remember somebody in the boardroom asked him if he ever considered the idea of running for president, and I remember him being very clear that that was something he was seriously considering.
You were on the Celebrity Apprentice season with Brande Roderick. We all saw the sexist comment Trump made to her on TV but there were also reports that Trump repeatedly propositioned Roderick throughout the season—despite being married to Melania. Did you ever witness any of that?
I never saw anything inappropriate, honestly. I never saw or heard anything like that. But I wasn’t privy to everything.
OK, let’s talk about Iron Sky: The Coming Race. You play a wacky cult leader who preaches “Jobsism,” a cult inspired by the teachings of late Apple co-founder Steve Jobs.
I rail on social media and in my stand-up about how technology is changing our perspective on human interaction and our relationships are permanently affected with people because we’re stuck on our phones all day. There are so many oddities about where we are as a society because of Steve Jobs, so I found it really interesting to become this psychotic-villain-megalomaniac character who’s a lot different from any character I’ve played on film before. Most of the characters I’ve done have been pure, over-the-top, silly comedy. Playing a villain is a lot of fun.
Right. It’s a very different role for you, this more subdued villain.
We shot over six weeks on these big sound stages in Antwerp. I enjoyed taking my energy levels way, way down. My show was on MTV, I did several movies, and I was running around on the streets of Ottawa with my VHS video camera before that—that was my introduction to acting, was pulling pranks on the street. My transition to film was very quick, and it takes a while to realize that you don’t need to have that high volume put into a performance. The older I get, I’m having more and more fun playing these more subdued characters.
How do you feel your comedy approach has evolved over the years? You got started taking the piss out of people on your Public Access show and then adopted a more confrontational approach.
I’ve always liked to try different things. I started out as a young kid, around 15, doing stand-up comedy in my high school days at Yuk Yuk’s in Ottawa, and whether it’s my podcasting, radio shows, talk shows…I’m guest hosting for Larry King right now, talking to all these amazing actors and performers, and it’s a totally different muscle. I’m not the goofball trying to be the center of attention on that show; I’m trying to create a comfortable environment for somebody else who has a lot to say. But my stand-up comedy is certainly not subdued. It’s a high-energy show with a lot of interaction with the crowd.
I really enjoyed your late-night show, The New Tom Green Show, but it seemed like MTV didn’t give it much of a chance.
The reason I started doing stand-up when I was a teenager was because I loved Late Night with David Letterman. I would say David Letterman is the reason I decided to get up onstage at a comedy club, because I loved his show and thought, “How did he get his start?”
Where do you think your rebellious or confrontational comedic streak comes from?
Look, my Dad was in the Canadian military, so before I settled in Ottawa in 7th grade, we were a military family. The first seven years of my life, we moved every year. Neighborhood friends changed entirely for me every year. Just as you were starting to get comfortable in a certain environment, we would move. And move again. Also, I was a super skinny kid. Much skinnier than anybody else that anyone had ever seen kind of thing. It was something that I was very insecure about, and I would show up at a new school and they would see this lanky kid walking in who was so skinny they couldn’t believe it, and I would have to try to make friends. I would often do that by tripping over a garbage can, or speaking out in class at the wrong time, or razzing the teacher and making everybody laugh. This is when I started realizing that this was how I could find happiness in life: by making other people laugh so that they would like me.
Freddy Got Fingered was absolutely killed at the time by critics but there’s been a sort of interesting cultural reappraisal of it in recent years.
I’d leave it to other people to come up with their own conclusion as to why people were so gleefully harsh about the movie. I was a young, 28-year-old, enthusiastic video prankster who was creating a bizarre show on MTV at the time, and had the opportunity to do something different and weird, and I was very fortunate to have the support of [producer] Arnon Milchan, New Regency, and 20th Century Fox, which went on to make films like The Revenant—and made one of my favorite movies of all-time, The King of Comedy.
Rupert Pupkin!
I feel like Rupert Pupkin sometimes, to be honest with you—building TV studios in my living room, and things like that. But Arnon Milchan told me when the movie came out that The King of Comedy got some very harsh reactions when it came out, and he said that 15, 20 years from now people may actually come out and say they love [Freddy Got Fingered]. And here we are, 20 years later, and he was right. It’s been an incredible thing that’s happened in the last two or three years. I can proudly speak about this because I love the movie. It was a reflection of where I was at the time—the naiveté of youth, and having the wide-eyed enthusiasm and the guts to go into a studio and fight for something as absurd as that movie. And we had to fight for it. And everywhere I go, whether it’s Hong Kong, Singapore, London, Sydney, not a day goes by where I haven’t stepped out of my hotel or my home in Los Angeles and somebody doesn’t come up to me and say, “Daddy, would you like some sausage?” It’s pretty cool. It’s brought me closer to a lot of people.
You’re out here guest-hosting for Larry King, touring across the country with stand-up. How do you feel things are going for you right now?
I’ve been very fortunate with my life. I’ve had very good people around me. When my show was at its peak, from 1999 to 2003, when I was making show after show and film after film, I was fortunate to have very good advisers and businesspeople around me. Things are great. I’m developing multiple television projects, and I’m touring and doing stand-up out of a total love of stand-up and a desire to grow as a stand-up comedian and get better at it.
