After Fifteen Years Of Silence, Drew Barrymore Shared An Emotional Reunion With Her Ex-Husband

Barrymore had invited Green onto her new show The Drew Barrymore Show, and he’d accepted. The famous actress has been using it to catch up with people from her past. The first episode featured her Charlie’s Angels co-stars Lucy Liu and Cameron Diaz plus her 50 First Dates leading man Adam Sandler.

For years Barrymore had been trying to get a talk show off the ground. She’d first started discussing it with Warner Bros. all the way back in 2016. By 2019 she’d shot a pilot, but it took until the next year for it to actually air. Once it did, it was a big success. Audiences loved Barrymore’s sweet optimism and charm.

Barrymore wanted the show to be a breath of fresh air in a difficult year. In September 2020 she told the Entertainment Tonight show, “I would have never been right for this job until this moment… I want to just look at everything from an honest perspective, a different perspective, a humorous perspective and a very real perspective in 2020.”

So for those who were expecting something incredibly dramatic to happen with Green, they might have been disappointed. There was no digging up old grievances, and definitely no screaming or throwing things. Both Barrymore and Green had grown up a lot since the ’00s, and they behaved like mature adults.

Barrymore even introduced him with a joke. She said, “I have always been attracted to visionaries, comedians and people who make me laugh. I was so attracted to our next guest, I even married him!” But how did the couple, who only actually had a few months of married life, get to that point?

Green and Barrymore first met at some point before the 2000 flick Charlie’s Angels went into production. On the show they actually spoke about their first date: the pair, both big animal lovers, went out and bought lobsters for the sole purpose of releasing them back into the ocean. Awww.

Seemingly Barrymore was actually a fan of Green before they began dating though. The comedian mentioned on The Alan Cox Show in 2018, “She and the studio were trying to get me in [Charlie’s Angels] for a while. I actually passed on it initially.” In 1998 People magazine described Barrymore as Green’s “galpal.”

From there we know much more, because the couple weren’t private about their relationship. In July 2000 – just as Green was coming out of a fight with testicular cancer – announcement of an engagement came. Green was set to appear with Barrymore in the Charlie’s Angels movie and then tie the knot with her.

It wasn’t the first time Barrymore had been engaged, or married. She’d had a pretty wild time of it in her teenage years. In 1994 Barrymore fell fast and hard for a Welshman named Jeremy Thomas, who owned a bar in L.A. She married him that year, at the age of just 19, but the marriage lasted a mere ten months. Hopefully, this one would last longer.

Needless to say, the news of Barrymore and Green’s engagement made headlines, although not always nice ones. At the time, the Orlando Sentinel newspaper wrote, “People still can’t believe it, but sometime the frog does get the princess. Actress Drew Barrymore, who stars in the upcoming film Charlie’s Angels, is engaged to marry MTV comedian Tom Green, her publicist said.”

If you were around at the time, you might remember the slightly ridiculous Saturday Night Live stunt that Green and Barrymore pulled while they were still engaged. Sadly, no clips of it for public consumption exist anymore, but the 2000 episode involved Green pretending that Barrymore would marry him on-air, only to have her abandon him at the end of the show.

At the time the media reported that a real on-air wedding would have taken place if Barrymore hadn’t gotten cold feet. According to Variety magazine, Green was absolutely ready to tie the knot in front of the Saturday Night Live audience, but his bride-to-be changed her mind at the last minute.

ABC News said at the time, “Wacky antics and self-humiliation are just par for the course for Green, but it turns out that he really did have everything ready for the wedding, including a license and a minister, until Drew decided (apparently five minutes before the ceremony) that it would be ‘inappropriate’ to marry on the air.”

Was that really the case though? Apparently not. Many years later, in 2019 Green told the Daily Beast website what really went down. He said the plan was, “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.”

Green went on, “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. And then at the end of the show, she doesn’t show up.”

However, Green’s dissatisfaction was more to do with the show than Barrymore herself. He said, “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!’ But in other ways, I think it just sort of ruined my Saturday Night Live experience.”

As it turned out, the couple got married for real in July 2001. And it was a big, fun wedding packed with celebrity guests. All of Barrymore’s biggest co-stars – Adam Sandler, Lucy Liu, and Cameron Diaz – were there. Eight-year-old Frances Bean, the daughter of Courtney Love and Kurt Cobain, served as the flower girl.

People magazine wrote of the bride and groom that they “had treated their nuptials (including a wedding teaser on Saturday Night Live last November) like a much prolonged April Fool’s joke. But when Barrymore approached the cliffside tent in a backless, lace-sleeved cream gown, carrying a bouquet of gardenias, attendees figured this was no gag.”

It was by all accounts a lovely wedding… but the actual relationship lasted such a short time in the end. In December 2001, just five months after saying “I do,” Green filed for divorce. The reason given for the split in the papers was “irreconcilable differences” – which ironically was also the title of a Drew Barrymore movie.

Both parties released statements and they were sad, not angry. Green said, “Drew is a wonderful woman, I love her very much. I wish our marriage could have worked out, I wish her much happiness.” And Barrymore said, “I love Tom very much. He has always been a great friend, and that won’t change.”

And from there, it was mostly radio silence about the relationship. Barrymore got married again to art consultant Will Kopelman in 2012 and had two daughters with him. But in 2014 Green did speak about his divorce to OWN’s Where Are They Now show and mentioned he hadn’t talked to Barrymore for “many, many years.” He wished her well, though.

Barrymore’s marriage to Kopelman ended in divorce as well, after four years together. Barrymore seemed to take this split harder than her one with Green. In 2016 she told Chelsea Handler on the show Chelsea, “It’s so shameful and hard to actually go through [divorce], even privately. It’s a tough time.”

During Barrymore’s meetup with Green she was still single, and it appeared that Green was too. But it wasn’t that kind of reunion. It was two friends catching up. Barrymore had made it clear in the media that she wasn’t ready to embark on any romances just yet. It all made for an unexpectedly touching scene.

Barrymore told Green, “We haven’t seen or spoken to each other in far too long.” Yet they shifted into the interaction of old friends right away, with Green saying, “Thanks for having me here, Drew. And I really, really couldn’t be more excited about your new show. It’s nice to see you every day on here, just bringing this burst of happiness, and energy, and optimism into the world right now.”

After exchanging those pleasantries, the pair shared some old memories in front of the camera. Green told Barrymore his parents said hello to her, and that they loved “watching you do amazing things.” That spurred Barrymore to remember a sweet moment in her life that had involved Green and his family.

Barrymore reminisced to her ex-husband, “I was at your parents’ lake house, and I remember hearing all their voices upstairs. I was by myself and going to sleep and I was like, ‘Yeah, this is what safety and contentedness feels like before you’re going to sleep.’ I love your parents, and I really love you and I celebrate you.” While saying this, she was almost crying.

Green had brought along an adorable dog: his name was Charlie, of course. The pair began talking about their experiences with Barrymore’s own dogs, including one scary incident when their house caught fire in the middle of the night. A very brave pet named Flossie had gotten them out of the building unharmed.

Barrymore also remembered the immediate aftermath of that incident. While watching the house burn down in the middle of the night, Green had sung the Entertainment Tonight theme to cheer her up. Barrymore quite fiercely told him, “In that moment… everything was so dark and scary and confusing, you lightened it up for me. You made me laugh!”

Green also delighted his ex-wife by pulling out a mug with an unflattering photo of her on it. It featured Barrymore in a brace after spraining her neck. The comedian joked, “I found this mug in my garage a couple of years ago and I just kinda kept it ’cause I figured someday I might be on your TV show, and it’d be fun to have a sip out of the mug.”

It was a lovely reunion, and both of them seemed overcome with happy emotions. At the end of the show Barrymore got tearful again while recommending Green’s new podcast. She told the audience, “I suggest you go through a library of Tom Green when you need it most. Or you just wanna… feel good.”

The episode was a resounding success. Green wrote on his Twitter account after it aired, “Was nice reconnecting with my ex-wife Drew Barrymore after all these years. Watch her new show everyone she is doing amazing!” In the comments, many fans cheekily suggested that the ex-couple should get back together.

And that wasn’t the last time Green appeared on Barrymore’s show. In December he popped up there again, and Barrymore revealed that the pair had been keeping in touch and even playing long-distance board games together. Barrymore adorably told him, “It’s so much fun to play Scrabble GO with you.”

And straight away the two just couldn’t stop complimenting each other. Green told his ex-wife, “You’re hilarious on the show, by the way. I’ll see on your Instagram these hilarious things you’re doing. Which to me, I just think it’s what daytime television needs, it needs a little more wackiness.”

Green went on, “I’ve had a lot of laughs watching your clips on social media… So congratulations, I’m proud of you, I’m so happy for you. Thank you.” A clearly very touched Barrymore responded, “If you think it’s funny, I’m happy because you are a pioneer of funny in a genre that did not exist before you.”

Barrymore’s been pretty adamant about never getting married again. In 2020 she told People magazine, “I never want to be entwined with someone like that again ever.” But that didn’t stop people commenting on her show and saying things such as, “They need to get back together!” and “Would you two just get remarried already.”

Come 2021, Barrymore got to discuss the sweet reunion with Jimmy Fallon on The Tonight Show. The host called the catch-up chat his “favorite interview” and Barrymore told him, “There were no questions prepared for that. I had an offline conversation with him because we didn’t want it to be some bougie Hollywood moment, like, ‘Let’s reconnect in front of the cameras.’”

Barrymore couldn’t help raving about Green to Jimmy Fallon as well. She said, “The thing I love about Tom is he is one of the first people to put a camera on his life, when it was a giant, fat camcorder and there were no easy phones available. His stuff was on VHS, I remember watching his VHS tapes. It’s what gave me the idea, because I just said, ‘Gosh, would you just want to reconnect?’”

The actress basically told him, “It’s been a long time, and I would just love to honor what you did. You broke down all these doors; you were a pioneer. And I would love to talk about it and have it be an excuse for us to say hello.” She sent him a video, and when he sent one back, “He made me laugh and that’s my kryptonite: laughter.”

Barrymore was delighted with the response to the interview. She told Fallon, “It was nice to hear from some people saying like, ‘I’d like to have with someone from my past.’ Whether it was a specific person, a lot of people were talking about how they’d like to have that type of exchange from someone who they had a significant chapter in their life with.” Now a whole new chapter seems to be starting.