If you were breathing in the year 2000, you couldn't escape the daisy-print, butterfly-clipping, high-kicking whirlwind that was Drew Barrymore. Honestly, it’s hard to overstate how much she owned that decade. While the tabloids were busy dissecting the "party girl" wreckage of other starlets, Drew was quietly—and then very loudly—becoming the most powerful woman in Hollywood. She wasn't just a face on a poster. She was the one hiring the director.
The Power Move: Flower Films and the Angels
Most people think of Charlie’s Angels (2000) as just a fun action flick with great hair. But look closer. It was basically a manifesto. Produced by her own company, Flower Films, which she started with Nancy Juvonen in 1995, the movie was a massive gamble. People in the industry were skeptical. A female-led action movie based on a 70s TV show? It sounded like a recipe for a flop.
Instead, it raked in over $260 million worldwide. Drew didn't just play Dylan Sanders; she dictated the tone. She wanted the "Angels" to be capable and tough without being "manly" about it. They didn't even use guns in the first movie because she thought it was cooler to show women winning with their wits and martial arts. That's a huge detail people forget.
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She was 24.
At an age when most actors are just happy to get a callback, she was managing a $90 million budget. It changed the math for women in the industry. By the time the sequel, Full Throttle, rolled around in 2003, she and her co-stars were commandingly high earners, proving that the "female ensemble" wasn't a fluke—it was a goldmine.
Rewriting the Rom-Com Rules
Then there’s the Adam Sandler of it all. You can’t talk about Drew Barrymore 2000s movies without talking about the chemistry that basically defined a generation of dating.
50 First Dates (2004) is the big one here.
On paper, the plot is kind of a nightmare: a woman with short-term amnesia (Lucy Whitmore) has to be "wooed" every single day because she forgets her boyfriend the moment she falls asleep. In the wrong hands, that’s a tragedy or a creepy thriller. But Drew brought this specific, sunny vulnerability that made it work.
Fun Fact: The Ending Wasn't Always Happy
Barrymore recently revealed on her talk show that the original script for 50 First Dates was actually a drama set in Seattle. It was called Fifty First Kisses. In the original ending, the guy (Sandler’s character) just leaves. He doesn't stay. He doesn't build the boat or make the tapes. Drew was the one who pushed for the pivot to comedy and the Hawaii setting, which, let's be real, saved that movie from being a total bummer.
She had this uncanny ability to pick projects that felt like a warm hug but had a weird, dark edge. Think about Donnie Darko (2001).
- Flower Films produced it.
- Drew played the English teacher, Karen Pomeroy.
- Without her star power and funding, that cult classic probably never gets made.
She was using her rom-com "sweetheart" capital to fund weird indie sci-fi about giant rabbits and time travel. That is a level of creative range we don't give her enough credit for.
That Specific 2000s Aesthetic
Style-wise, Drew was the antidote to the "polished" look of the era. While everyone else was doing the ultra-glam, sleek aesthetic, she was showing up to premieres in:
- Cropped green jackets and white flares (E.T. 20th Anniversary).
- Huge silk flowers tucked behind her ear.
- Beaded chokers and blue-tinted glasses.
It was "boho-chic" before the term was ruined by fast-fashion brands. She looked like she’d just come from a flea market, even when she was wearing Dior. There was a relatability there. She had over-plucked eyebrows—just like the rest of us—but she wore them with a "so what?" attitude that made her an icon for girls who didn't feel like they fit the Britney Spears mold.
The Pivot to "Serious" Acting
By the end of the decade, the industry started to realize she wasn't just the "fun girl" anymore. In 2009, she took on the role of "Little" Edie Beale in Grey Gardens.
If you haven't seen it, find it. It’s a total transformation. She spent hours in makeup to look like a reclusive, aging socialite living in a decaying mansion. She won a Golden Globe and a SAG Award for it. It was the ultimate "I told you so" to anyone who thought she was just the girl from The Wedding Singer.
She capped off the 2000s by directing her first feature film, Whip It (2009). A roller derby movie starring Elliot Page. Again, it wasn't a "safe" choice. It was gritty, fast, and very much about female friendship. It didn't break box office records, but it solidified her as a filmmaker who actually cared about the stories she was telling.
Why it Still Sticks
Drew Barrymore in the 2000s wasn't just a career; it was a survival story. We all knew she’d been through the ringer as a kid. We knew about the rehab at 13 and the emancipation at 14. Seeing her thrive in the 2000s felt like a win for the underdog. She wasn't just "back"—she was the boss.
What you can do now to appreciate this era:
- Watch the "Angels" Commentary: If you can find the old DVD extras, listen to her talk about producing. It’s a masterclass in creative leadership.
- Revisit Donnie Darko: Watch it specifically through the lens of Flower Films. Notice how she uses her small role to ground the movie’s high-concept weirdness.
- Study the Grey Gardens Transformation: Compare her performance to the original 1975 documentary. The vocal work alone is insane.
She taught a whole generation that you can be soft and kind while still running the boardroom. You don't have to be a shark to win in Hollywood; sometimes, you just have to be a Flower.
Next Steps for the Nostalgic:
To truly understand the Barrymore impact, go back and watch Never Been Kissed (1999) followed immediately by Grey Gardens (2009). The ten-year jump shows the most radical evolution of any actor in that time period. You’ll see exactly how she moved from "Josie Grossie" to a decorated dramatic powerhouse.