Anthony and Joe Russo’s “You, Me and Dupree” often gets forgotten among the sea of brilliant 2000s rom-coms. “What Women Want,” “Amélie,” “Bridget Jones’s Diary,” and “Love Actually” are just some of the popular movies from the decade that overshadow the Russo Brothers’ offering.
However, despite its underwhelming 21% approval rating on Rotten Tomatoes, it’s a funny and often heartfelt film with a great cast. That cast includes Owen Wilson, Kate Hudson, Matt Dillon, and Michael Douglas.
It follows a pair of newlyweds, played by Hudson and Dillon, as the groom’s best man and best friend, Wilson’s eponymous Randolph “Randy” Dupree, loses his job and home, and moves in with them.
“You, Me and Dupree” was a moderate financial success, grossing a worldwide total of $130.6 million, having cost $54 million to produce (per Box Office Mojo).
Released in the United States on July 14, 2006, it will celebrate its 20th anniversary this year. With that in mind, wouldn’t it be fun to see how the core cast look now compared to when the film hit theaters? Let’s do that now…
Owen Wilson (Randolph “Randy” Dupree)
GettyActor and Academy Award-nominated screenwriter Owen Wilson played Randolph “Randy” Dupree in “You, Me and Dupree.” Dupree is a laid-back and jobless slacker who moves in (and outstays his welcome) with his newlywed best friend after losing everything. His antics drive the movie’s story.
Age when “You, Me and Dupree” released: 37.
Selected movie credits before “You, Me and Dupree”: Zoolander (2001), The Royal Tenenbaums (2001), Wedding Crashers (2005).
GettyAge now: 57.
Selected movie credits after “You, Me and Dupree”: Marley and Me (2008), The Internship (2013), Marry Me (2022).
Filmography info per IMDb.
Kate Hudson (Molly Peterson)
GettyAcademy Award-nominated actress and singer-songwriter Kate Hudson played Molly Peterson in “You, Me and Dupree.” Molly is a schoolteacher and the charming, patient wife of Dupree’s friend Carl, with whom Dupree moves in. She’s the emotional anchor trying to keep her marriage intact amid the disruption caused by Dupree’s antics.
Age when “You, Me and Dupree” released: 27.
Selected movie credits before “You, Me and Dupree”: Almost Famous (2000), How to Lose a Guy in 10 Days (2003), Raising Helen (2004).
Above is a 2026 social media post by Kate Hudson with over a dozen recent pictures of her.
Age now: 46.
Selected movie credits after “You, Me and Dupree”: Bride Wars (2009), Glass Onion: A Knives Out Mystery (2022), Song Sung Blue (2025).
Filmography info per IMDb.
Matt Dillon (Carl Peterson)
GettyAcademy Award-nominated actor Matt Dillon played Carl Peterson in “You, Me and Dupree.” Carl is Molly’s husband and Dupree’s best friend with whom Dupree moves in. His chaotic life is made worse by the pressures of his job and Molly’s disapproving and demanding father.
Age when “You, Me and Dupree” released: 42.
Selected movie credits before “You, Me and Dupree”: The Outsiders (1983), There’s Something About Mary (1998), Crash (2004).
GettyAge now: 62.
Selected movie credits after “You, Me and Dupree”: The House That Jack Built (2018), Asteroid City (2023), Being Maria (2024).
Filmography info per IMDb.
Michael Douglas (Bob Thompson)
GettyTwo-time Academy Award-winning actor and producer Michael Douglas played Bob Thompson in “You, Me and Dupree.” Bob is Molly’s father and Carl’s demanding boss who makes his son-in-law’s life difficult.
Age when “You, Me and Dupree” released: 61.
Selected movie credits before “You, Me and Dupree”: Fatal Attraction (1987), Wall Street (1987), Basic Instinct (1992).
GettyAge now: 81.
Selected movie credits after “You, Me and Dupree”: Last Vegas (2013), Ant-Man (2015), Looking Through Water (2025).
Filmography info per IMDb.
Seth Rogen (Neil)
GettyCanadian actor, comedian, and filmmaker Seth Rogen played Neil in “You, Me and Dupree.” Neil is a quirky friend and colleague of Carl’s.
Age when “You, Me and Dupree” released: 24.
Selected movie credits before “You, Me and Dupree”: Donnie Darko (2001), Anchorman: The Legend of Ron Burgundy (2004), The 40-Year-Old Virgin (2005).
GettyAge now: 43.
Selected movie credits after “You, Me and Dupree”: Superbad (2007), The Green Hornet (2011), The Fabelmans (2022).
Filmography info per IMDb.
Amanda Detmer (Annie)
GettyTelevision and movie actress Amanda Detmer played Annie in “You, Me and Dupree.” Annie is Neil’s controlling wife who barely lets him do anything.
Age when “You, Me and Dupree” released: 34.
Selected movie credits before “You, Me and Dupree”: Boys and Girls (2000), Saving Silverman (2001), Kiss the Bride (2002).
Above is a 2026 social media post by Amanda Detmer with a recent picture of her.
Age now: 54.
Selected movie credits after “You, Me and Dupree”: AmericanEast (2008), Pure Country: Pure Heart (2017), A California Christmas (2020).
Filmography info per IMDb.
It’s great to see the core cast of “You, Me and Dupree” are all still doing so well. If it’s a movie you’ve never seen, or have actively avoided based on its Rotten Tomatoes rating, we urge you to give it a chance — it’s a fun and easy watch that’s better than it’s given credit for.
