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Tom Green was never more famous than when he hosted Saturday Night Live on Nov. 18, 2000. 

Not only was his insanely popular talk show still airing on MTV, he was coming off a scene-stealing performance in the hit comedy Road Trip.  Just weeks earlier, Charlie’s Angels, in which Green appeared opposite his new fiancée Drew Barrymore, debuted at No.  1 at the box office. 

“It was an amazing thing to have gotten to do it,” Green says of his SNL experience, 19 years later, on this week’s episode of The Last Laugh podcast.  However, he adds, “I think if I could go back and do it again someday, I would do it a lot differently.” 

When producer Lorne Michaels offered Green the chance to host that fall, the comedian insisted that his childhood friends from Canada, whom he had hired as writers on The Tom Green Show, come in for the week and help write sketches. “ I didn’t understand the politics of Saturday Night Live,” he says, acknowledging that SNL’s writers at the time, including Mike Schur, who would go on to create The Good Place, future Oscar nominee Adam McKay and head writer Tina Fey, may not have appreciated the input. 

“I was aggressively trying to deconstruct everything that I encountered,” Green explains. “ Just because I was a kid in my twenties and I was like, that’s the way you do it.  Let’s try to take it apart and put it back together upside down and inside out.” 

“I think in hindsight I would have rather just shown up and worked with everybody else and just kind of went with the flow a bit more,” he adds. “ But I was young and passionate.”  Green says his friends ended up writing about half of the sketches that aired in his episode, including one in which he appeared in a bathtub with Lorne Michaels as well as his monologue and the final sketch of the night. 

Green’s big idea for the episode was a gag that would be teased at the beginning of the show and pay off in the final moments.  His relationship with Barrymore was all over the tabloids and he thought it would be funny if they appeared together during his monologue and announced they would be getting married on live television at the end of his SNL debut. 

“I try not to have regrets, but that is something that I actually regret,” Green says. “ So Drew and I actually were engaged at the time.  So we thought, this will be a funny prank.  We’ll prank the audience.  We’ll tell everyone we’re going to get married on SNL and then she won’t show up at the altar at the end and that will be the punchline.  Even though we were still getting married, like a month after.  That was the bit.” 

“But the thing I regret about that bit to this day, which I’m actually sad about, to be honest with you, is that the way we wrote the bit, we kept teasing that we were going to get married at the end of the show—she’s out in the hallway in her wedding dress, my parents are there in the audience,” he continues. “ And then at the end of the show, she doesn’t show up.  And the end of my SNL I have a meltdown on stage.  And it’s a complete meltdown and the band stops playing and the entire cast disappears and I’m just standing alone on stage at the very end of the show.” 

“Artistically,” Green still thinks it was a “pretty awesome” way to end the show. “ But it does sort of ruin my beautiful Saturday Night Live kumbaya moment,” he says. “ At the end of every Saturday Night Live, [the host] is hanging out with the cast and celebrating together.”  But on his episode, it’s just Green screaming “I thought you loved me!”  on stage by himself. 

“In some ways, it’s kind of a metaphor for the rebellious, naive kid that I was: ‘We’re going to go there and we’re going to try to turn SNL upside down!’”  he says. “ But in other ways, I think it just sort of ruined my Saturday Night Live experience.”  He does add that he and Barrymore went to the after party with the cast and “had a blast.” 

Green maintains that it was one of the highest-rated episodes that season “because of” the prank. “ It was a massive success in that sense, because we did create a reason to stay up ’til the end,” he says. 

According to a Variety item from that week, the “cancelation” of the wedding was “sprung on Lorne Michaels only five minutes before the ceremony was to take place on camera” and the show reportedly had a priest and City Hall license on hand.  Caroline Kennedy, Tom Hanks, Rita Wilson, Gwyneth Paltrow, Cameron Diaz, and Harvey Weinstein were among the celebrities waiting backstage to celebrate with the “newlyweds” after the show. 

To “put it in perspective how crazy” his life was at that time, Green tells me that the morning after Saturday Night Live aired, he and Barrymore got on a plane to London to have dinner with Prince Charles at St. James’s Palace for the royal premiere of Charlie’s Angels. 

Green sat next to Camilla Parker Bowles at the dinner and had a two-hour conversation about “stuff like France and organic farming” among other topics. “ Was it a real mouse?”  Prince Charles asked Green of the infamous scene from Road Trip in which he attempts to feed a snake and ends up putting a live mouse in his mouth.  The answer was yes. 

Green and Barymore ultimately did get married in July of 2001 and were divorced less than nine months later.  Green has called their marriage a “crazy whirlwind of a time.” 

“So it was a bizarre time in my life,” Green tells me.  If he ever gets the chance to host SNL again, “which would be nice,” he says, “I would love to be able to not bring my friends from high school in and not try to make it some crazy, warped episode.” 

Nearly two decades later, the 48-year-old comedian chalks the whole thing up to “the naivety of youth.” 

“I had been so hellbent on causing chaos everywhere I went that suddenly when I was where I was, I still was behaving as if I was living in my parents’ basement,” Green says. “ I should have probably taken certain opportunities to just be grateful that I was there.  And I didn’t realize that at the time.” 

Next week on The Last Laugh podcast: Stand-up comedian and star of ABC’s Black-ish and Grown-ish, Deon Cole.