You, Me and Dupree is billed as a comedy, but one minute it’s a romance, then it’s a drama, and then it’s a rom-com. The film juggles stress management, companionship, motivational speaking, love, jealousy, and cycling. Some may say it has it all, but – in truth – it possesses too much to maintain its intentions. At points, it is difficult to discern if the film is striving to be a male bonding escapade or a rescue mission in disguise. Frankly, as far as sticking with a particular tone goes, You, Me and Dupree is hit and miss. It’s intermittently humorous; hence, it’s often unfunny and tedious.
After getting married and honeymooning in Hawaii, Carl (Matt Dillon) and Molly (Kate Hudson) Peterson return to their home to open their wedding gifts, write their thank-you cards, and create a conjoined answering-machine message. However, once Carl learns that his best man, Randy Dupree (Owen Wilson), was fired and has no place to stay, Carl invites Dupree to “stay” at the Peterson house for a few days. When a few days turns into interrupted sex, street fights, HBO, foul odors, strippers, and more, Molly and Carl begin to regret their invitation.
Meanwhile, Carl’s father-in-law and boss (Michael Douglas) continues to show Carl no respect — except for offering him a promotion that doesn’t exactly pan out as expected. As a result, an exceedingly stressed Carl has to maintain his place in the household and look to rid his home of Dupree.
Between Carl and Dupree, both characters unwisely transform at the speed of light. Dupree quickly transitions from a low-life loser and an unemployed inconvenience to a sappy poem writer and a lonely charmer. Likewise, Carl goes from a loving newlywed husband to an angered outsider in his own living space. The final third in the trio, Molly, remains constant. But, with the men tangling their identities, it makes it hard to root for one specifically and become attached to both.
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