If you were around in the mid-2000s, you couldn't escape the blonde, sun-kissed energy of Owen Wilson and Kate Hudson. They were the "it" people of the rom-com world. So, when they finally teamed up for a flick, everyone expected lightning in a bottle. What we got was You, Me and Dupree.
Honestly, it’s one of those movies that feels like a time capsule. You’ve got Matt Dillon playing the straight man, a pre-superstar Seth Rogen in the background, and Owen Wilson basically playing... well, Owen Wilson. But the real story isn't just about what happened on screen. It’s about the chaos that followed behind the scenes.
Why You, Me and Dupree Still Matters (Sorta)
The premise is basically every newlywed’s worst nightmare. Carl (Matt Dillon) and Molly (Kate Hudson) get married, and Carl’s best man, Randy Dupree (Wilson), loses his job and his house. Naturally, he moves in.
He stays. And stays.
He clogs the toilet after eating too many buffalo wings. He accidentally sets the house on fire. He’s the houseguest from hell who somehow manages to be more charming than the actual husband. It’s a classic "arrested development" story that was super popular back then. Think Wedding Crashers but with more domestic strife and way more couch-surfing.
The movie actually did okay at the box office. It pulled in about $130 million worldwide against a $54 million budget. Not a flop, but critics weren't exactly lining up to give it Oscars. It’s sitting at a 20% on Rotten Tomatoes.
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Ouch.
The critics' main beef? It felt a bit generic. But if you're looking for that specific 2006 vibe—low-stakes comedy and "wow" factor—it still hits the spot.
The Kate Hudson and Owen Wilson Connection
Here’s the thing people usually forget: Kate and Owen didn't just play love interests (or whatever you'd call their weird dynamic in the movie). They actually started dating in real life.
They met on the set in 2006. Kate had just split from her husband, Black Crowes frontman Chris Robinson. Suddenly, the tabloids were losing their minds. You couldn't walk into a grocery store without seeing their faces on a magazine cover.
It wasn't a smooth ride. Their relationship was very on-again, off-again for about three years.
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The Real Drama
Things got heavy in 2007. There were reports that the breakup hit Owen Wilson incredibly hard. During this time, he was hospitalized after a serious personal crisis, which led to him dropping out of the movie Tropic Thunder (Matthew McConaughey ended up taking his role).
It was a rare moment where the glossy, happy-go-lucky world of Hollywood rom-coms crashed into real-life struggle. Kate and Owen eventually tried to make it work again in 2008 and 2009, but they officially called it quits for the last time in mid-2009.
Despite the drama, they’ve both spoken pretty kindly about each other since then. In 2023, Kate even joked about her past romances on The Drew Barrymore Show, keeping things light. It seems like enough time has passed that the "Dupree" days are just a wild memory.
A Weird Beef with Steely Dan?
This is my favorite piece of trivia about this movie. It is so bizarre you couldn't make it up.
The legendary rock band Steely Dan actually called out Owen Wilson because of the movie. Why? Because they have a song called "Cousin Dupree" about a creepy, couch-crashing relative. They wrote this hilarious, tongue-in-cheek open letter to Luke Wilson (Owen’s brother) accusing Owen of "theft" of their character's vibe.
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They even invited Owen to come on stage and apologize to their fans.
Owen's response? He basically said he’d never heard of the song and didn't even know who "Mr. Steely Dan" was. He then joked that he was working on his next movie, Hey 19 (which is another Steely Dan song). It was top-tier celebrity trolling before Twitter even existed.
Watching It Today: What You Need to Know
If you’re planning a rewatch, keep your eyes peeled for the supporting cast.
- Michael Douglas: He plays Kate Hudson’s dad and he is surprisingly intense.
- Seth Rogen: He’s Carl’s other friend. This was right before Superbad turned him into a household name.
- The Directors: Believe it or not, this movie was directed by Anthony and Joe Russo. Yeah, the guys who directed Avengers: Endgame.
It’s wild to think the guys who handled the biggest superhero showdown in history started out with Owen Wilson naked on a couch.
Actionable Tips for Fans
If you're in the mood for this specific brand of mid-2000s comedy, here is how to get the most out of it:
- Check the Streaming Rotation: As of 2026, the movie bounces between Netflix and Peacock. It’s rarely on both at the same time, so check your "Watchlist" apps.
- Double Feature Idea: If you want the full "Owen Wilson Era" experience, pair You, Me and Dupree with Wedding Crashers. They feel like they exist in the same cinematic universe where no one over the age of 30 wants to get a real job.
- Look for the "Unrated" Version: There’s an unrated cut on DVD and some digital platforms. It doesn't change the plot, but it adds some of the more "crude" humor that the Russo brothers originally wanted.
- Skip the Sequels: There aren't any. Hollywood realized that one Dupree was probably enough for everyone.
The movie might not be a masterpiece, but the chemistry between the leads and the sheer weirdness of the production era make it worth a look if you’re feeling nostalgic. Just don't let any of your friends move in "for a few days" after you watch it. You’ve been warned.
To dive deeper into Owen Wilson's filmography, you should check out his work with Wes Anderson, specifically The Royal Tenenbaums, to see a completely different side of his acting range compared to his Dupree persona.