Hollywood is a weird place where people become family for three months and then never speak again. It's the nature of the beast. But sometimes, a specific pairing just sticks in the collective memory of the public because the chemistry felt less like "acting" and more like a genuine, messy, beautiful life being lived on screen. That's exactly what happened with Brittany Murphy and Drew Barrymore.
If you grew up in the late 90s or early 2000s, you probably remember them together in Riding in Cars with Boys. It wasn't just another teen flick. It was this gritty, often heartbreaking biographical drama directed by Penny Marshall. Drew played Beverly Donofrio, and Brittany played her ride-or-die best friend, Fay Forrester.
Honestly, it’s one of those movies that hits differently now.
Seeing them on screen together is a bittersweet experience because of everything we know about how their lives unfolded. You've got Drew, the ultimate survivor who reinvented herself a dozen times, and Brittany, whose light was extinguished far too soon. Their connection—both in the film and in real life—represented a very specific era of Hollywood that felt more raw and less curated than what we see on Instagram today.
That Time Brittany Murphy and Drew Barrymore Fooled Everyone
One of the funniest things about their relationship is how much they actually looked alike at one point. In an old interview from Interview Magazine, Brittany told Drew about a time she was shooting Sidewalks of New York. She was rocking short blonde hair, very 1995-era Drew.
A fan literally chased her down the street screaming, "Drew Barrymore! Oh my god!"
Brittany thought it was hilarious. She wasn't offended; she actually leaned into it. She told Drew that the fan was "very sweet" but just a little confused. It’s a tiny anecdote, but it shows the vibe between them. There wasn't this weird, competitive energy you often see between starlets. They were just two women who respected each other’s craft and occasionally got mistaken for one another in a New York minute.
Riding in Cars with Boys: More Than Just a Movie
When people search for Brittany Murphy and Drew Barrymore, they're usually looking for that specific magic they captured in 2001.
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In Riding in Cars with Boys, they played two teenage girls who both end up pregnant at the same time. The scene where they touch their pregnant bellies together is iconic. It wasn't just "movie magic." It felt like a real bond. They represented a type of female friendship that isn't about being "perfect" or "aesthetic." It was about being broke, scared, and stuck in a small town, but having that one person who won't let you drown.
Critics at the time, like those at The Austin Chronicle, pointed out that while the script was sometimes a bit "modulating," Brittany and Drew brought a level of character depth that saved the film. Brittany, in particular, was praised for being "wonderful to watch." She had this way of taking a supporting role and making it feel like the heart of the story.
Why the Film Still Ranks High for Fans
- The "Anti-Fairytale" vibe: It’s used by some online communities as a "scared straight" movie for teens because it shows the reality of young parenthood.
- Authenticity: Penny Marshall (the director) pushed for a realist portrayal.
- The Chemistry: You can't fake the way these two looked at each other.
The Emotional Legacy and "The Drew Barrymore Show"
Fast forward to the present day. Brittany Murphy passed away in 2009 at the age of 32. It’s still one of the most talked-about and tragic losses in entertainment. Drew hasn't forgotten her.
On The Drew Barrymore Show, Drew has frequently revisited her memories of Brittany. In one particularly moving segment from late 2025, she reflected on Brittany’s character. Drew basically said that one of the most painful things about losing her—aside from the obvious tragedy of a life cut short—was just how "wonderful" she was.
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"She wasn't a Hollywood girl," Drew remarked.
That’s a huge statement coming from someone like Drew Barrymore, who grew up in the literal belly of the beast. To Drew, Brittany was the same person in a room full of stars as she was at home. She was authentic. In an industry built on smoke and mirrors, that’s rare.
What Most People Get Wrong About Their Connection
Some people assume they were inseparable best friends for decades. That’s not quite right. They were colleagues and friends who shared a very intense, transformative experience while filming. They were "work sisters."
But there’s a nuance there.
In Hollywood, "work sisters" can often be more influential on an actor's life than actual childhood friends because you’re in the trenches together. You’re doing 16-hour days. You’re crying in trailers. You’re figuring out how to be famous while still trying to be a person. Drew has acknowledged that Brittany’s energy was infectious. Even if they weren't hanging out every single weekend for ten years, the impact Brittany left on Drew was permanent.
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How to Celebrate the Brittany Murphy and Drew Barrymore Legacy Today
If you’re feeling nostalgic and want to dive deeper into this specific pocket of pop culture history, you don't need a time machine.
- Watch "Riding in Cars with Boys" again. But watch it for the background details. Look at the way Fay (Brittany) reacts to Beverly (Drew) when things go wrong. It’s a masterclass in supportive acting.
- Look for the "From the Vault" interviews. The Interview Magazine archives have some gems where they talk to each other. It’s way better than a standard press junket.
- Check out the 2021/2025 clips from Drew’s show. She brings on people who knew Brittany, like astrologers or old co-stars, to keep her memory alive in a way that feels respectful rather than gossipy.
The story of Brittany Murphy and Drew Barrymore isn't just a "where are they now" or a tragic retrospective. It’s a reminder of a time when Hollywood felt a little more human. It’s about two women who looked similar, acted their hearts out, and reminded us that friendship is the only thing that actually gets you through the "bumpy ride" of life.
If you're looking for more authentic 2000s cinema, your next step should be checking out Brittany's performance in Spun or Girl, Interrupted. It shows a totally different side of the range she brought to the table alongside her work with Drew.