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Shooting Dupree
The cast in place, the crew would now address the challenges of the film's location shoots. It seemed logical (and fortunate) to all involved to film the movie's opening honeymoon sequences on the exotic isles of Hawaii.

You, Me and Dupree commenced principal photography October 7, 2005, on a sunny pineapple field in Kaawa, Hawaii, on the island of Oahu. The mood on set was "pure holiday,” thanks to the filmmakers' decision to shoot Carl and Molly's wedding, reception and honeymoon over the first ten days of filming.

One of the first scenes shot for Dupree is best man Randolph Dupree's late arrival for the rehearsal. Rushing into the island in a small crop duster—because he first landed on the wrong island—Dupree arrives with a bang. Carl and one of his groomsmen, Neil, played by Seth Rogen, are impatiently waiting to meet him.

"Starting this movie in Hawaii got everyone off on the right foot,” notes Wilson. "We were all able to bond outside of work in a great environment, and since we play a group of friends who have known each other for years, it set the mood for what followed on screen. It was a natural way to create continuity amongst everyone.”

"What better way to start a shoot than having a good time in beautiful Hawaii?” laughs director Anthony Russo. "This was the honeymoon phase where all of the characters were getting to know one another. Hawaii was the perfect setting for that.”

For the newlywed Le Sieur, crazy bachelor parties are a reality that he's witnessed in his own life. "The most natural thing for a guy to do before he gets married is to hang out with his buddies and get goofy,” says Le Sieur. "It's akin to watching another one of the crowd go off the plank. In this case, the call of the wild for just one more night is too seductive, even for Carl. Watching Matt, Owen, Seth and the rest of the groomsmen throwing down drinks felt exactly like watching some of my own buddies.”

Newly golden tan, the cast and crew headed back to Los Angeles, where the filmmakers spent four days in Irvine, California—in one of the endlessly slick office buildings that would serve as The Thompson Development Company. The empire was where Mr. Thompson could conduct business and torture his son-in-law/employee, Carl, with a litany of passive-aggressive insults.

"My character feels very much at home in this environment,” says Douglas. "The elements of faux spiritual statues sprinkled throughout all this glass and steel create a perfect background for Mr. Thompson to humiliate and demean his new son-in-law. It really sets up his character.”

A lovely old Craftsman house in the historic section of Gramercy Place in central Los Angeles was chosen for the exterior shots of Carl and Molly's home, where much of the story takes place. It was here that Carl, Molly and Dupree would navigate many of the trips and pratfalls that come with filming this type of comedy.

"I like doing physical comedy,” notes Dillon. "It's definitely part of the fun of making movies. Although Carl plays the straight man to Dupree, every once in a while he gets sucked into Dupree's arrested-development shenanigans.”

Production continued to zigzag in and around the city of Los Angeles—lensing at the school where Molly teaches in East Los Angeles to the docks off of San Pedro, where seven-time Tour de France champion Lance Armstrong makes a cameo appearance on Mr. Thompson's fishing boat.

Armstrong served not only in a cameo role in this film, he also became a theme.

A hero and inspiration to many, Armstrong was a natural icon to become the object of Dupree's obsession at achieving success…through an unconventional route. In Dupree's case, though he begins cycling to get into shape, his aspiration to greatness is taken to the nth degree, adding yet one more item to help raise


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