You, Me and Dupree 2006
"Two's company. Dupree's a crowd."
In *You, Me and Dupree (2006)*, acclaimed directors Anthony Russo and Joe Russo (making their feature debut) blend sharp wit with heartfelt chaos in this 2006 comedy-romance.
Director: Anthony Russo
Cast
Owen Wilson
Dupree
Kate Hudson
Molly
Matt Dillon
Carl
Michael Douglas
Mr. Thompson
Seth Rogen
Neil
Amanda Detmer
Annie
Ralph Ting
Toshi
Todd Stashwick
Tony
Bill Hader
Mark
Lance Armstrong
Lance Armstrong
Frequently Asked Questions
What is You, Me and Dupree (2006) about?
The film follows Carl Petersen, whose life takes a chaotic turn when his unemployed best man, Randy Dupree, overstays his welcome after the wedding. What begins as a temporary fix spirals into a hilarious battle of wills as Dupree's presence threatens Carl's marriage and sanity.
Who directed You, Me and Dupree?
*You, Me and Dupree* was directed by the Russo brothers (Anthony and Joe Russo), who later gained fame for their work on Marvel blockbusters and *Avengers: Endgame*.
Who stars in You, Me and Dupree?
The film features Owen Wilson as Randy Dupree, Kate Hudson as Molly Petersen, Matt Dillon as Carl Petersen, Michael Douglas in a supporting role, and Seth Rogen as a lovable side character.
Is You, Me and Dupree (2006) worth watching?
While not a critical darling, *You, Me and Dupree* delivers solid mid-2000s comedy charm with Owen Wilson's trademark humor and a fun ensemble cast. If you enjoy lighthearted rom-coms with a side of slapstick, it's a decent pick for a fun movie night.
How long is You, Me and Dupree?
The runtime for *You, Me and Dupree* is 108 minutes, or 1 hour and 48 minutes.
🎥 Trailer
About You, Me and Dupree (2006) — A Comedy About Friendship Gone Too Far
In *You, Me and Dupree (2006)*, acclaimed directors Anthony Russo and Joe Russo (making their feature debut) blend sharp wit with heartfelt chaos in this 2006 comedy-romance. The film follows Carl Petersen (Matt Dillon), who unwittingly invites his free-spirited best man, Randy Dupree (Owen Wilson), to crash at his place after a string of bad luck leaves him jobless and adrift. What starts as a temporary stay spirals into an awkward houseguest situation, with Dupree's infectious charm and relentless optimism straining Carl's new marriage to Molly (Kate Hudson). As tensions rise and lines blur between friendship and overstaying one's welcome, the film explores themes of loyalty, boundaries, and the absurdity of unexpected roommates.
With its sunny California backdrop and a stellar ensemble cast—including Michael Douglas as Carl's eccentric boss and Seth Rogen as a perpetually hungry sidekick—the movie balances slapstick humor with moments of genuine emotion. The Russo brothers craft a comedy that feels both timeless and perfectly of its era, making *You, Me and Dupree* a standout in the mid-2000s rom-com revival.
