The movie begins with Molly Thompson (Kate Hudson) and Carl Peterson (Matt Dillon) a few days before their wedding in Hawaii. Theyve just gone to the beach, and as theyre sipping margaritas and getting cozy with each other, the door bell rings. Its Carls friend Neil (Seth Rogan). He mentions something about Dupree (Owen Wilson) getting lost. Carl is obviously surprised, as it cant possibly be that hard to find an island in Hawaii. They arrive at the airport just as Dupree lands in a rickety small plane. He apologizes to Carl, saying that he got confused out there. All is forgiven, and they share a guy moment.
Flash forward to the pre-wedding dinner. Mollys father, Mr. Thompson (Michael Douglas), is making a speech about the upcoming wedding. He explains how when Molly first told him that she wanted to marry Carl; hed asked her who he was. He shared with the guests that when Molly told him that Carl was actually one of his employees, hed been afraid that Carl was some young chap trying to pry the family business straight out of his hands. He then laughs and tells them that he can see now Carl is no threat. Everyone laughs, Dupree included, and Carl shoots him a glare. Dupree stops laughing and gives him an apologetic smile.
Everyone is soon gathered around at the bar. After sharing a toast to Carl, Dupree offers to do the Flaming Tornado, something of a tradition between the guys, as Dupree has done it at every single celebration since they could remember. At the same time, Molly calls Carl over because her aunt is here, and she wants to talk to Carl. Dupree, on the other hand, is all set to do the Tornado. Carl chooses to go speak with Mollys aunt, and upon noticing this, Dupree immediately stops and tells the eager crowd that hell do it when Carls back. Neil doesnt understand this show of friendship and jumps on the counter in Duprees place.
After Neil injures himself with the Tornado, Carl talks a bit with Dupree out on the beach. Dupree apologizes for laughing during the reception, and tells Carl that he shouldnt let it get to his head because Carl has a Carlness. He explains it as a glimmer in his eyes that tells people that they just cant break him. Its actually quite inspiring, but perhaps because of the few drinks that Dupree had, its not totally making sense to Carl. Dupree then tells Carl that he wonders if theres something that they could do to his bridegrooms shirt to show that hes the Best Man. He suggests something subtle a lightning bolt perhaps. Carl is a little surprised, and tells him that its mentioned in the program. Dupree pretends to be satisfied, but Carl understands.
At the wedding, along with the Hawaiian themed bridegroom shirt that the other guys are wearing, Dupree has a small emblem of a lightening bolt in a circle with the capital letters BM (Best Man) inside. He wears a proud smile as the happy couple walks down the aisle.
Carl and Molly are immensely happy together, and we see them inside their new house surrounded by wedding gifts. They decide to split the work of writing thank you cards 50 cards each. While enjoying a small feast, they record the typical newlywed message on their phone.
The next day, Carl returns to work at Thompson Land Development, only to be surprised by Mr. Thompson himself, who read Carls ideas while the couple was on their honeymoon. He tells Carl that he loves it and shows him a picture of a vast desert area, which he proudly announces is where they will build Oaks at Mesa Vista, Carls idea. Carl tries to tell Mr. Thompson that he had originally planned for Oaks to be a smaller, more personal piece of construction, but is unable to fight Mr. Thompson. During their conversation, Mr. Thompson brings up the topic of Mollys last name. Mr. Thompson seems determined to have Molly keep her last name and even suggests that Carl hyphenate his own. Carl is clearly offended and declines Mr. Thompsons offer. He has, however, been given a promotion, so he quickly calls Molly and tells her. Shes a teacher at an elementary school, and shes ecstatic for Carl. She tells him that theyll have a celebration tonight in honor of him, and Carl is more than happy to accept.
After work, however, Carl heads off to the local bar, where he sees Neil and Dupree having a great time. Unfortunately for Neil, his wife is incredibly overbearing, and he leaves almost immediately. Dupree, on the other hand, was fired for taking a week off to attend Carls wedding and is currently living in a cot at the bar. Carl is shocked to see his old friend reduced to living at the bar, but not nearly as shocked as he is to hear that the other regulars want Dupree out. He offers Dupree his home, even though Dupree politely objects.
A rather guilty Carl arrives home to find Molly in bed with candles all over the place. He announces that Dupree has nowhere to stay and asks if he can stay with them for awhile. Molly is completely against it, after all, theyve just gotten married! Carl agrees, but tells her that itll only be for awhile. It takes him a few minutes to notice all the preparation Molly went through for him. He apologizes again, but runs out to bring Dupree in, much to Mollys chagrin.
Dupree lugs in his belongings, including a zebra patterned beanbag chair and a giant moose head. Molly is absolutely horrified at the sight of Dupree, but manages to be polite about it. They explain a few rules about living with them, and start to go upstairs. Dupree suddenly interrupts, telling them that he understands that as newlyweds, theyll want to be intimate with each other. Molly rolls her eyes at Duprees frankness, but he goes on.
The next morning, Molly and Carl find Dupree sprawled completely naked on the couch. Again, the couple is shocked. Duprees first few days are completely chaotic. Asides from becoming friends with the neighborhood kids, Dupree is hardly any help in the house. Due to his rather free-spirited nature, its difficult for Dupree to find a job. Instead, he stays home and, amongst other things, makes the toilet overflow, goes upstairs to the couples private bathroom, and interrupts their intimacy. Molly is incredibly frustrated, and wants Dupree out. Instead, she decides to hook Dupree up with the new librarian at the elementary school. Dupree consents, and when the couple return from a night out on the town, they find Dupree and his date getting hot and heavy right in the middle of their living room. Molly nearly faints from the horror of it, and when Dupree accidentally sets the house on fire, she announces that its the last straw.
Carl is forced to kick Dupree out, but that doesnt make the present state at home any easier. Things are tense with the missus, and things at work are even tenser. Mollys father dislikes Carl, and has been hinting for Carl to get a vasectomy. Carl is continuously working overtime even though Mr. Thompson has made Carls ideas completely unrecognizable. With Dupree out of the house, however, things are starting to calm down. Molly and Carl go out for dinner, but as theyre driving back in heavy rain, they find Dupree sitting on a bench, looking rather lost and forlorn. Molly cant stand the sight of the poor guy just sitting out there, so she insists that they bring him back.
This time around, its Carl whos setting the rules. He tells Dupree that things cant be the way they were before if Dupree wants to stay here. He has to help out around the house and get his life together. Dupree tells Carl sincerely that he can be very helpful when he sets his mind to it, so Carl asks Dupree to write a half of the thank you cards when he has the time. Dupree gets to work the very next day, starting with the burnt living room. He repaints the entire room, and helps Carl and Molly refurnish it. Meanwhile, hes taken to riding his bike with the local bike racers, and finishes up Carls half of the cards.
When Carl is unable to make it to a Career Day presentation at the elementary school, he asks Dupree to fill in for him. Dupree does a fine job with the kids, giving a rather inspirational speech. Dupree wants Molly to bring the librarian, Mandy in, so she can hear his speech, but when he finishes, Molly tells him that Mandy ended up sleeping with half of the male faculty. Mollys become very fond of Dupree (although not in the romantic sense of the word), and she doesnt understand why Carl is working such late hours. Dupree tries to patch things up between the couple, and tells her that Carl has never been a feelings kind of guy. He tells her to keep trying, because thats what he did, and when he finally got Carl to crack, it was worth it. When Carl returns from work later that night, Molly tries to get him to talk to her. She tells him that Dupree writes poetry, to which Carl replies What a homo. Molly tells Carl that hes being very immature, but Carls too tense to say much. Molly asks Carl to come home a little earlier from work the next day because Duprees offered to make them dinner. Carl agrees, although somewhat hesitatingly, but come tomorrow, Carls late once again.
Molly is sick and tired of Carls irresponsibility, and since Duprees already made the dinner, they decide to enjoy it together. Carl returns with a small bouquet of flowers only to find Dupree and Molly having a great time. He begins to suspect an affair, but its Dupree who throws a fit and goes into the kitchen. Molly and Carl fight in the bedroom, but nothing is resolved. Molly cant sleep, so she goes downstairs. Unfortunately for her, Dupree is well, pleasuring himself, and in the ruckus of it all, they wake Carl up as well.
Carl is incredibly suspicious of Molly and Dupree, and asks Dupree where he found the porn to begin with. Dupree tells him that it was in a box labeled Carls Camping Equipment. Carl quickly asks whether Dupree put the box back or not. Dupree said that he did, but Mollys cry from the kitchen says otherwise. Carl admits to Molly that hed gone through a phase where hed become very fond of Asian porn, but that hes over it now. Molly, now angrier than ever, tells Carl to get rid of the box.
Carl blames Dupree for his marital problems and suspects him of trying to seduce his wife, so he kicks him out. The next morning, Molly tells Carl that her father is coming over for dinner that evening. Carl objects, but Molly just glares at him and tells him not to be late. Carl knows that Mr. Thompson dislikes him, after all, he invites everyone he likes to go fishing with him. At the dinner, things are going rather roughly when they hear a crash from the roof. Its Dupree, come to retrieve his things. Molly invites him in, and Mr. Thompson takes a liking to him immediately. Before dinner, Mr. Thompson had told Carl that he was being demoted again, and Carl took it rather badly. Its difficult for Carl to watch his best friend hitting it off with a father-in-law who always hated him. An image of Dupree on a yacht with Molly and Mr. Thompson shakes in Carls mind, and something in him just breaks.
Carl leaps across the table and begins to strangle Dupree. After Mr. Thompson whacks him with a candlestick, Carl marches out of the house. He tries to crash at Neils, but Neils wife wont let him. The next morning, Dupree finds Molly with swollen eyes and messy hair. She tearfully tells Dupree that Carl didnt come home last night. Dupree organizes a search team composed of the neighborhoods kids, but the search is in vain.
Having run out of places to look, Dupree ends up at the bar, where he finds Carl downing drink after drink. He shows Carl a packet of love poems he wrote for Mandy, not Molly. He tries to convince Carl to return to the house, but theres no use. Finally, Dupree walks away, saying that he never thought Molly and Carl made a good match anyway. He tells Carl that shes pretty fake anyway, and doles out insult after insult. Carl jumps up and tells Dupree that Molly is the best thing thats ever happened to him. At this, Dupree sits back down and tells Carl that it was just a trick; Carl has to go back there and get his ness back.
Inspired by Duprees speech, Carl and Dupree head back to Thompsons office. Dupree distracts the guard, Poco, by running around the building. He tells Poco that hes throwing at least seven different kinds of smoke today and starts the chase. Dupree ends up falling through the roof just as Carl finishes his talk with Thompson. Dupree and Carl return to the house as heroes, and Dupree jumps for joy (literally) as the couple reunites. They agree to work their problems out from now on instead of walking out.
Fast forward a couple months (or years?) Dupree is giving a motivational speech to the employees of Thompsons Land Development company, and Poco is his DJ. Dupree introduces his new book, appropriately titled Seven Different Kinds of Smoke: Finding Your Inner-ness
*CUT TO THE CHASE*
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Newlyweds Molly and Carl, (Kate Hudson and Matt Dillon) allow Carl's best friend Dupree(Owen Wilson) to live with them after he loses his house. Dupree acts like a total kid which gets on Molly's nerves. Molly decides to set Dupree up on a date. When Molly and Carl return home they find Dupree having sex with his date. One thing leads to another and candles that Dupree lit catch the house on fire. Carl makes Dupree leave.
Later on when the couple is driving they find Dupree in the rain with nowhere to go. Molly lets Dupree come back to their house.
As time goes by Dupree becomes a better person and he and Molly starts to connect. Due to the fact that Molly's dad who happens to be Carl's boss (Michael Douglas) has been treating Carl like shit, he has to work all the time. Molly gets hurt by this and turns to Dupree. As time goes by Carl gets jealous of Dupree which leads to a physical conflict. Carl then runs off.
Dupree spends most of the end of the movie looking for Carl. When he finds him, he convinces him to take a stand against Molly's dad. They do and it leads to a chase sequence between Dupree and a big guard named Paco.
In the end Carl confronts Molly's dad and he agrees to give Carl a break. End of the story is that Molly and Carl work everything out and Dupree becomes an author and a motivational speaker.
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