When you think about the absolute peak of early 2000s comedy, names like Ben Stiller and Drew Barrymore usually sit right at the top of the list. He was the king of the neurotic slow-burn. She was the queen of the quirky, infectious rom-com smile. Put them together and you've got a billion-dollar recipe, right? Well, Hollywood thought so too.
But here is the thing: they actually only made one movie together as co-stars.
Just one.
The film was Duplex (2003), a dark comedy directed by Danny DeVito that basically asked the question: "How far would you go to get a rent-controlled tenant out of your dream house?" It’s a weird, mean-spirited, and oddly fascinating relic of an era when studios were willing to spend $40 million on a movie about two people trying to accidentally-on-purpose kill an old lady.
The Reality of Ben Stiller and Drew Barrymore Movies
It’s easy to misremember this. You’ve probably scrolled through Netflix or watched a TikTok compilation and sworn they were in 50 First Dates or Along Came Polly together. They weren't. Stiller was busy with Jennifer Aniston and Christine Taylor; Barrymore was the iconic duo-partner for Adam Sandler.
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In Duplex, they play Alex and Nancy. They're a "perfect" New York couple—he’s a writer, she’s a magazine editor—who buy a gorgeous Brooklyn brownstone. The catch? The upstairs tenant, Mrs. Connelly (played by the late, great Eileen Essell), comes with the building. She’s sweet. She’s tiny. She’s also a literal demon who plays her TV at max volume and ruins their lives through "favors."
Why Duplex Didn't Hit the Way People Expected
Honestly, the chemistry was... complicated. Some critics at the time, like the late Roger Ebert, felt the movie was too mean-spirited to be truly funny. It’s a "black comedy" in the truest sense. You’re watching two likable A-listers descend into homicidal madness.
- The Humor: It’s slapstick mixed with genuine spite.
- The Direction: Danny DeVito brought the same cynical energy he used in The War of the Roses.
- The Box Office: It didn't do great. It pulled in about $19 million against that $40 million budget.
There’s a scene where Stiller’s character tries to catch a "killer flu" in the subway just so he can sneeze on the old lady's popcorn. It’s dark. It’s uncomfortable. And yet, if you’ve ever lived in an apartment with a neighbor who won’t stop vacuuming at 3:00 AM, it’s kinda relatable? Sorta.
The "Benjamin Rabbit" Connection
Even though they didn't keep making movies together, they stayed friends. Recently, on The Drew Barrymore Show in early 2025, Ben Stiller showed up to promote Severance and they dropped some behind-the-scenes gold.
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Drew actually has a nickname for him: Benjamin Rabbit.
She’s called him that for over 20 years. It started on the set of Duplex. It’s those little details that make you realize why the movie has a cult following now. Even if the script was a bit "off-putting" (as some reviews claimed), the actual bond between the actors was real. Stiller even mentioned on the show that he had "the best time" working with her, despite the movie being a bit of a "turkey" in the eyes of critics back then.
A Quick Look at the Duplex Stats
| Feature | Detail |
|---|---|
| Director | Danny DeVito |
| Release Year | 2003 |
| Budget | $40 Million |
| Rotten Tomatoes | Around 35% (Critics) |
| Fun Fact | Released as "Our House" in the UK |
Why They Never Teamed Up Again
Hollywood is a business of "if it works, do it ten more times." Since Duplex underperformed, the Stiller/Barrymore pairing wasn't fast-tracked for a sequel or a new rom-com. Stiller moved deeper into directing and darker roles (think Severance), while Drew leaned into her talk show and production empire through Flower Films.
Interestingly, both of them were producers on Duplex. They weren't just hired guns; they were invested in the project. The movie failed not because of their talent, but because the tone was a tough sell for 2003 audiences who wanted "happy Drew" and "zany Ben," not "murderous Drew" and "depressed Ben."
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The Legacy of the Pairing
If you watch it today, Duplex feels like a time capsule. It captures that specific New York real estate anxiety that has only gotten worse in 2026. The film explores the "Seven Deadly Sins," specifically envy. We want what they have, but then we watch them lose their souls trying to keep it.
Honestly, it’s worth a rewatch if only to see Eileen Essell absolutely steal the show from two of the biggest stars on the planet. She was 80-plus years old at the time and had more energy than both of them combined.
How to Experience Their Work Today
If you're looking to dive into the world of ben stiller and drew barrymore movies, you've basically got one main course and a lot of "adjacent" content.
- Watch Duplex: It’s available on most VOD platforms. Watch it for the "Benjamin Rabbit" energy and the sheer absurdity of the third act.
- Check out The Drew Barrymore Show clips: Search for the January 2025 episode where Ben Stiller visits. Their shorthand and "old friend" vibe is actually more charming than the movie itself.
- Follow the Production Credits: Both have produced massive hits. If you like the vibe of their collaboration, look into Red Hour Productions (Stiller) and Flower Films (Barrymore).
The biggest takeaway? Not every "A-List" pairing results in a franchise, but sometimes that one-off weirdness is exactly what makes a movie memorable 20 years later.
To get the most out of this niche film history, your best move is to watch Duplex through the lens of a "dark property satire" rather than a standard rom-com. It changes the whole experience from a "flop" to a biting commentary on the lengths people will go for a few extra square feet of living space.