Who: Golden Globe-winning actress, producer, and beauty boss Drew Barrymore, 45, and comedian Tom Green, 49.
How They Met: According to Green, he and Barrymore met when the actress was trying to get him on board for Charlie’s Angels (in which he famously played “The Chad”). As per IMDb, production began in early January 2000, so they likely first met at some point in 1999.
“She and the studio were trying to get me in that movie for a while,” Green said on The Alan Cox Show in 2018. “I actually passed on it initially.”
After a couple years of dating, the pair wed in July of 2001 before a crowd that included all of Charlie’s Y2K Angels (Cameron Diaz, Lucy Liu), Adam Sandler, and even Courtney Love. Love and the late Kurt Cobain’s daughter, Frances Bean, served as the flower girl.
Why We Loved Them: If the class clown was a couple, it would be Barrymore and Green. The MTV prankster and the former child star were to quirky hijinks what Angelina Jolie and Billy Bob Thornton were to bodily fluid-bearing jewelry. You’d be hard-pressed to find a photo of the couple where Green wasn’t staring defiantly at the camera and/or pointing. They had their bit.
Of course, Green was a polarizing figure for the media, considering his penchant for pranks.
In November of 2000, Green hosted Saturday Night Live, where he pulled off a prank so convincing that outlets wrote it as straight news. During his monologue he asked Barrymore to marry him at the end of the show. But once the show reached its conclusion, Barrymore appeared to have left him at the altar. It was reported that the Never Been Kissed star decided last-minute that it would be “inappropriate” to tie the knot on TV.
Nearly two decades later, Green told The Daily Beast that he regretted the prank. “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. 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.” And though, yes, he agreed the prank was “pretty awesome,” there was one problem: “It does sort of ruin my beautiful Saturday Night Live kumbaya moment.” Instead of celebrating with the cast in the episode’s final moments, Green was “screaming ‘I thought you loved me!’ on stage by himself.”
This wasn’t the last time Green’s sense of humor would confuse the media, however. The following spring, Green appeared on The Tonight Show and told host Jay Leno that Barrymore was pregnant. He later walked the comment back in a statement, explaining, “People always think I’m kidding about stuff. Jay and I were joking around, and I thought the audience was in on it. We are not pregnant now, but do hope to be blessed with children in the future.”
When They Peaked: In February of 2001, Barrymore and Green’s L.A. home burned down in a fire. They were able to escape unscathed, thanks to their dog, Flossie, who woke them up in the middle of the night by barking and banging on their bedroom door. “Flossie was really the main alert that there was a fire,” Barrymore’s spokesperson told The L.A. Times.
The news received the SNL treatment that week, with Katie Holmes and Jimmy Fallon impersonating the couple in a sketch where Maya Rudolph played a reporter on the scene.
Admittedly, this is more about when Flossie peaked. RIP Flossie.
After about five months of marriage, Green filed for divorce, citing “irreconcilable differences.”
"Drew is a wonderful woman, I love her very much," Green said in a statement at the time. "I wish our marriage could have worked out, I wish her much happiness."
Barrymore released a similarly heartfelt statement: "I love Tom very much. He has always been a great friend and that won't change."
Neither party discussed the relationship (or its end) for many years. In 2015 Barrymore spoke about Green at the behest of Watch What Happens Live host Andy Cohen. "Tom Green, I think, is a very unique human being,” she said. "I think that he did something before anyone else did. I think he was a real pioneer. There was no social media. There was no reality TV, and I have to say, I gave him a lot of credit, as a creative person onlooking, that he was the first, and I do appreciate that about him.”
In 2017, Green described the marriage as “part of that sort of crazy, whirlwind of a time,” noting he hadn’t spoken to his ex for “many, many years,” though he was “really happy that she’s doing good.”
When asked outright why the marriage ended during an episode of Sway in the Morning in 2018, Green kept it vague, explaining, “It was a lot of pressure at the time. I was probably new to show business … I’d just gone through cancer as well — I had testicular cancer — so it was just probably a lot of stresses.”
Where They Are Now:
Barrymore later married her third husband, Will Kopelman in 2012. They welcomed daughter Olive, 7, and Frankie, 6, before announcing their separation in 2016.
Green has yet to re-marry.
#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time.
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