You, Me and Dupree

Molly (Kate Hudson) and Carl (Matt Dillon) are preparing for their wedding day in Hawaii, until Carl's friend Neil (Seth Rogen) interrupts to say that Dupree (Owen Wilson) got lost. They drive off together to pick up Dupree, who appeared to have hitched a ride with a light plane after landing on the wrong island. A day before the wedding, Molly's father Thompson (Michael Douglas), who is also CEO of the company that Carl works for, makes a toast with humorous remarks at Carl's expense, foreshadowing a conflict between the two. Dupree laughed a bit too loudly at Thompson's jokes. Later at a Pre-celebration at a bar, Carl neglects Dupree to be with Molly (as she wanted to introduce Carl to her grandmother) while he is about to perform a drinking tradition called the "Flaming Tornado". Carl and Dupree later make up on the beach, as Dupree apologizes for laughing at Molly's father's jokes, and tells Carl that he has "Carlness." Dupree says that Carl has that optimistic bent of mind that will never let anything, or anyone get to him, and asks him never to lose that. Carl and Molly get married. When Carl returns to work, at Molly's father's Thompson Land Development, he is surprised to find that Mr. Thompson has promoted him to be in charge of a design he proposed, though it had been altered somewhat. Carl had proposed a small 40-unit community, but Thompson decides to super-size it to several hundred units. The project is named "Oaks at Mesa Vista", and yet the site selected by Thompson has no trees at all. Mr. Thompson makes absurd requests which proceed to get worse, starting with Thompson's drastic re-imagining of Carl's new architecture project, requesting that Carl take the Thompson name instead and that Carl get a vasectomy to prevent childbearing later on. Before returning home to celebrate his promotion with Molly, Carl stops by the bar, where he finds Neil and Dupree. After Neil leaves due to his wife's curfew, Dupree reveals that he was fired, as he apparently did not have clearance to attend the wedding (his boss claimed that he never got Dupree's email), subsequently falling behind in his rent and evicted. Losing his car also, as it was the company's. Dupree was planning to sleep in the back room at the bar, but some of the regulars complained that Dupree got to sleep at the bar, and they didn't, so the cot was removed. Carl takes Dupree home, asking Molly if he can stay for a little while until he gets back on his feet. Molly is polite, though clearly frustrated as he is disruptive and messy. We learn that Dupree was a copier salesman at his last job. The next morning, Molly and Carl come down from their room all dressed for work and find Dupree, still sleeping on the couch, naked. While Molly and Carl are at work, Dupree engages the neighborhood kids in a game of baseball and causes a brawl by encouraging the kids to play aggressively. Molly sets up Dupree with a woman at her work, a primary school, who is a Mormon librarian. Dupree agrees, though Molly is shocked to find them having sex when she comes home from dinner. Romantic candles that Dupree had set up burn down the front of the living room, and Dupree is kicked out. Meanwhile Carl is being continually stressed out from work, though he and Molly find time to go out for dinner. On the way back they find Dupree sitting on a bench in heavy rain with his belongings. Molly insists they take him back in. Carl makes it known that Dupree must behave this time. The next day, Dupree makes amends, refurbishing the living room, and doing Carl's thank-you letters, as well as making friends with kids from the block. Carl asks Dupree to go to career day at Molly's work as he got tied up at his work and that night Dupree cooks a large dinner for Molly, though Carl is late again, so Molly and Dupree start without him. When Carl finally shows up, he is a little jealous that they were having dinner together and have a fight. Carl kicks Dupree out, suspecting an affair, which shocks Dupree. The following night, Mr. Thompson is over for dinner. Dupree climbs the drain pipe and sneaks inside to get his bags back, and during dinner the guests inside hear Dupree fall off the roof. Dupree is found outside and is invited in for dinner. After Bob takes a liking to Dupree and asks him to go fishing with him, it enrages Carl because - even though he does not like fishing - it is Bob's way of approving someone. Carl's fury boils over as he then imagines Dupree hanging out with Bob and having sex with Molly, causing Carl to jump across the table and attempt to strangle Dupree. Thompson hits Carl over the head with a candlestick shortly after and Molly kicks Carl out of the house. After returning from the hospital with a neck brace, Dupree and Molly confront Bob about what he really thinks of Carl, and his evasive answers reveal his dislike of him. The next morning Dupree gets all the local kids to search for Carl. Dupree eventually finds Carl in the bar and convinces him to chase after Molly. Dupree helps Carl break into Mr. Thompson's office, as Dupree distracts Paco, the security guard, whilst Carl marches into his father-in-law's office and confronts him. The two finally reach an understanding and Thompson admits to his agenda of insulting Carl. Dupree and Carl return to the house, where Carl and Molly reunite, Carl apologizing, and agree to work it all out. Glad that he mended Carl's marriage, Dupree celebrates by leaping into the air with joy until he falls to the ground. Dupree uses his experiences with Carl and Molly to publish a successful self-help book titled 7 Different Kinds of Smoke: Living, Loving, and Finding your Inner "-ness" and becomes a motivational speaker, with Paco as his assistant. In a post-credits scene, Dupree's hero Lance Armstrong reads Dupree's book and repeats "Lanceness" with various inflections.