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Comic Actors Join The Cast
With Owen Wilson signed on for the title role, the production team turned their attention to casting the film's other key roles. Their first order of business was to find actors to play Molly and Carl Peterson, the new bride and groom who would be the target of Dupree's adulation and accidental mischief.

In approaching the role of Molly, Wilson and Le Sieur agreed with Stuber, Parent and the Russo brothers that one of the keys to the film was ensuring that Molly was absolutely, adorably likeable.

"One of the first names that came up to play Molly was Kate Hudson,” says Le Sieur. "It would be easy for Molly to come across as nagging. She has to put up with a lot—especially being newly married—and we didn't want that. Kate is so loveable that she brings genuine sparkle to the character. She's luminous, definitely a burst of light that lets the audience know immediately why Carl is in love with her.”

Anthony Russo agrees that the team never looked at any of the three main players as the ultimate antagonist, especially Molly. "There are moments in the film where each one plays the role of antagonist, but they're imminently sympathetic.”

Continues Joe Russo, "With Kate, her charisma is stunning, and that was so important for this character. She gives Molly such texture, charm and charisma.”

"This is the first time I've ever gotten to play the straight guy in a comedy,” laughs Hudson. "It's a lot harder than I thought, because if you're not really grounded it doesn't work. Molly is mostly deadpan, and acting with Owen is such a crack up, that it was hard for me to play it straight and not break up.”

Matt Dillon's character, Carl, arguably has the toughest arc in the movie. In the beginning, he has it all: he's confident, sexy, the alpha male in his group and newly married to his boss' daughter. But as the story evolves, so does he…unfortunately, it's in the wrong direction.

"With Matt, you get the added heavy artillery of an amazing dramatic actor who has very good comedic instincts. He knows how to give something an extra twist so the character doesn't become too dark,” offers Stuber. "By the end of the second act, his entire paradigm has shifted and he really starts to unravel. Dupree's intrusion into his marriage—plus his father-in-law's pressure at work—has caused Carl to become unglued. There's not one aspect of his life that has not become embroiled in chaos.”

Joe Russo feels, "Matt was able to come in and provide a center to his relationship with Dupree and his marriage to Molly. At the same time, we get a lot of comedy from his character's unraveling as he is squeezed from all sides.”

For Dillon, You, Me and Dupree offered the chance to interpret a character not traditionally associated with his work. "Carl is the protagonist in this story. It's his journey,” Dillon reflects. "Carl's reaction to the insanity unfolding around him is what makes things interesting—even when his actions only make things worse. The only way the audience can laugh at his misfortunes is if they know he's a guy who can take it.”

With Wilson, Hudson and Dillon cast as the trio, the filmmakers next turned to finding an actor to play the powerful and prominent father-of-the bride, Mr. Thompson. The dream cast was complete when Michael Douglas agreed to play Molly's dad. He brought an instant identification to the character of Mr. Thompson, a man who carries the weight and intimidation of power and wealth. Douglas' history of acting choices ensured that the role of Thompson fit like a glove.

Director Anthony Russo offers, "Thompson is this fabulously rich guy, so we wanted to find a father-daughter combo that would be really intimidating to someone like Carl. Enter Michael Douglas.”

Echoes producer Stuber, "One cannot think of Douglas' iconic role as Go

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