It was the peak of the MTV era. You had a guy who once painted his parents' house plaid and another person who was, well, America's sweetheart. When Tom Green and Drew Barrymore got together, nobody really knew what to make of it. It felt like a glitch in the Hollywood simulation.
They met on the set of Charlie's Angels back in 2000. Drew was producing and starring; Tom was playing "The Chad." Honestly, if you look back at that movie now, their chemistry is actually kind of sweet in a chaotic, "we both grew up way too fast" sort of way. They eloped in July 2001. By December, it was over.
The Chaos Before the Vows
People forget how intense those few months were for them. This wasn't just a "celebrity fling." It was a trial by fire—literally.
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Before they even walked down the aisle, their house in the canyons burned to the ground. They were lucky to get out alive. Drew’s dog, Flossie, actually barked and banged on their bedroom door to wake them up while the roof was basically melting. Can you imagine? You're 26 years old, your house is an "ACME cartoon" of flames, and you're standing on a hill watching everything you own turn to ash.
And then there was the health scare. Tom was diagnosed with testicular cancer right as his career was exploding. He did a whole MTV special about it—which was unheard of at the time—and Drew was right there by his side through the surgeries and the fear.
- The Meeting: Charlie's Angels set, 2000.
- The Engagement: July 2000.
- The Wedding: July 7, 2001, at a private Malibu estate.
- The Guest List: Small, but included Cameron Diaz and Courtney Love.
Why the Tom Green Drew Barrymore Marriage Didn't Last
So, what happened? Why did the guy who made a career out of being "the weirdest man on TV" and the actress who survived the 80s as a child star fall apart so fast?
Most people assume it was just a prank that went too far. Tom was famous for pranking the world—remember when they joked for months about being married before they actually were? Or when Tom told Jay Leno they were having a baby when they weren't? It made it hard for the public to take them seriously.
But the reality was more human. Drew eventually opened up to Howard Stern about it, saying they were "young and kind of idiots." She described herself as a "woman in the boardroom and a child in the bedroom," meaning she could run a movie studio but didn't have the emotional tools to navigate a high-pressure marriage while their lives were quite literally on fire.
The divorce was filed on December 17, 2001.
That’s less than six months of marriage. In the paperwork, they cited "irreconcilable differences," which is the Hollywood standard for "we just can't make this work." Tom's official statement back then was actually quite tender. He called her a wonderful woman and said he wished her nothing but happiness.
The 15-Year Silence
Here is the part that usually shocks people: they didn't speak for fifteen years. Not a text. Not a "happy birthday." Nothing.
When you go through a house fire and cancer together, you'd think there would be some lifelong bond. But sometimes, when a relationship is forged in that much trauma and intensity, you just have to walk away from the whole thing to breathe. They both moved on. Tom eventually retreated from the Hollywood machine to live in a van and do photography (which is very on-brand for him), and Drew became a daytime TV mogul.
That Emotional 2020 Reunion
Fast forward to September 2020. The world is in the middle of a pandemic, and Drew Barrymore has just launched her own talk show. She decides to invite Tom on.
It was an out-of-body experience for both of them.
They sat there—socially distanced, because of the times—and cried. They talked about the "Annie Hall phase" Tom got Drew into by buying her a Pentax K1000 camera. They talked about the time they bought live lobsters at a grocery store and released them into the ocean because they couldn't stand the thought of them being eaten.
Tom even pulled out a coffee mug he’d found in his garage. It had a picture of Drew wearing a neck brace after she sprained her neck doing yoga decades ago. He’d kept it all that time.
It wasn't a "we're getting back together" moment. It was a "I'm so glad we both survived" moment.
Lessons From a Whirlwind
What can we actually learn from the Tom Green Drew Barrymore saga?
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First, intensity doesn't always equal longevity. You can love someone through a crisis and still not be right for them in the quiet moments. Second, there is a lot of power in a graceful exit. Neither of them ever trashed the other in the press. They kept it classy even when the world was laughing at the absurdity of their pairing.
If you’re looking to understand why certain relationships burn out fast, look at the external pressures. Most couples don't survive a total loss of property and a cancer diagnosis within their first year of dating.
Next Steps for Content Seekers:
- Watch the 2020 Reunion: If you want to see what true closure looks like, find the clip of Tom on The Drew Barrymore Show. It’s a masterclass in being an "elegant ex."
- Check Out Tom's Photography: He credits Drew with getting him into it, and his work now is actually stunning and deeply contemplative.
- Revisit Charlie's Angels: Watch it through the lens of their real-life romance; you can see the exact moments they were falling for each other.
The story of Tom and Drew isn't a tragedy. It’s just a very specific, very weird, and ultimately very sweet chapter of pop culture history that proved even the most chaotic beginnings can end with a peaceful "hello."