Matt Dillon plays Carl Peterson, a designer of housing communities who is newly married to Molly (Kate Hudson). His best man, Randolph Dupree (Owen Wilson), is one of those amiable-but-misguided souls who can’t ever quite manage to get things right. For instance, when traveling to the Hawaiian wedding, he lands on the wrong island and must be picked up. Dupree is a good guy, though, so everyone overlooks his penchant for mishaps.

After the nuptials, Carl discovers that his old pal is sleeping on a cot in the back of their favorite bar. Having taken an unauthorized vacation to attend the wedding, Dupree has been fired from his job. With no paycheck, he also got kicked out of his apartment. Carl feels guilty that Dupree has suffered consequences just to be part of the wedding, so he invites his friend to stay at the house until he gets back on his feet. Molly is initially opposed to the idea (they’re newlyweds, after all; they have lots to do – wink wink, nudge nudge) but she ultimately relents.

Dupree turns out to be the houseguest from hell. What is supposed to be a one-week stay stretches much longer, and he violates his hosts’ personal boundaries in all kinds of ways. He upgrades their cable service without permission. He fondles himself in the middle of the living room late at night. He nearly burns their house down after a sexual tryst goes awry. An exasperated Molly finally orders Carl to give his friend the boot. Through a series of circumstances too lengthy to go into here, Dupree leaves temporarily but then returns, only to cause more problems.

This is amusing for a little while, but eventually I noticed that You, Me and Dupree was starting to repeat the basic joke over and over again: Well-intentioned Dupree screws something up, causing stress for the newlyweds. The script tries to vary things by having Molly and Dupree eventually bond, much to the dismay of Carl, who flies into a jealous rage. Even with this flip-flop, the movie still seems to be stuck in a loop. The constant repetition of the central comic idea makes the movie feel like a two-hour pilot for a mediocre sitcom.

Dupree is not the only troublemaker. There is a whole subplot involving Molly’s land developer father, Mr. Thompson (Michael Douglas), who also happens to be Carl’s boss. He uses various passive-aggressive techniques to undermine the marriage, including suggesting that Carl have a vasectomy. Where the Dupree plot line is repetitive, the one involving Mr. Thompson is downright confusing. There is no apparent reason for him to hate Carl, so we are left with little reason to laugh at his insidious cruelty.

You, Me and Dupree has a terrific cast that it uses in strange ways. Matt Dillon and Kate Hudson both have comedic skills, but they’re stuck playing straight man to Owen Wilson. Why cast them in a comedy if they can’t be funny? Michael Douglas is supposed to get laughs as the meddling father/boss; he might have gotten them had his character’s animosity toward Carl been satisfactorily explained. Most sensibly cast is Wilson, who plays his trademark oddness at full pitch, making Dupree as a surfer dude turned space cadet. I like the actor a lot, but quite frankly, the character got on my nerves a little bit.

This is one of those movies that made me chuckle a few times, but it never really made me laugh. An occasional bit of business works, including a supporting performance from Seth Rogan (The 40 Year-Old Virgin) and a humorous sequence involving Carl’s hidden box of pornography. The actors also generate some good will. I enjoyed seeing them together, even if I would have preferred to see them in a better movie.

The film isn’t a total wash; it begins with an interesting idea, yet doesn’t know how to develop it. The movie needed a better second and third act. It also needed to aim a little higher. You, Me and Dupree obviously wants to be a Meet the Parents-style knee-slapper. The jokes rarely rise above the level of bathroom and sex gags, though. Like the main character, the movie is okay at first but eventually wears out its welcome.

( out of four)

Note: This is somewhat off-topic, but I noticed something curious here. Actress Amanda Detmer (Final Destination, Saving Silverman) is listed prominently in the opening credits, yet she’s virtually nowhere to be found in the actual film. I caught a quick glimpse of her in the background of one shot, and we hear her voice coming from off-screen later on. Did all her scenes hit the cutting room floor? I ask only because certain other elements (Thompson’s hatred of Carl) also seem to be missing. This makes me wonder if You, Me and Dupree was edited according to focus group responses.

You, Me and Dupree is rated PG-13 for sexual content, brief nudity, crude humor, language and a drug reference. The running time is 1 hour and 48 minutes.