With Wilson and Vaughn signed on, the filmmakers turned their attention to casting the supporting roles in the film. First order of business was finding an actor to play the role of the powerful and prominent Treasury Secretary, William Cleary.
“Secretary Cleary is the linchpin of this movie,” says Dobkin. “The way you cast the role dictates if the film is going to be a little bit of a classier comedy with some intelligence, or if it was going to be a very broad comedy with little intelligence. The film’s basically about these two guys who go to the Treasury Secretary’s mansion to scam on his daughters, so I felt the character better be somebody that John and Jeremy were scared of because it would raise the stakes of the comedy.”
In Dobkin’s eyes, there was only one perfect choice for the role.
“Christopher Walken was my first choice because he has a certain intimidation factor about him, but more importantly his performances in Catch Me If You Can and The Dead Zone have a certain warmth to them that I wanted to inject into the character. Chris also has an unbelievable sense of comedic timing and could create laughs out of a role where there wasn't necessarily a lot of comedy written on the page. Once we got him on board, it really galvanized the casting process.”
For Walken, an Academy Award-winning actor whose film resume is as diverse as the many memorable characters he has portrayed, the role of Treasury Secretary was one that caught him a little off guard.
“I was really surprised when I got the call to see if I was interested in the film,” admits Walken. “When you combine my own personality and background with the kinds of parts I’ve played in the past, it doesn’t lead me to believe that I would be cast as a political figurehead who’s entrusted to control and keep up with the country’s money. I have always played characters a little bit on the outside, so it’s a nice change of pace to play a family man with three daughters.”
It is at the lavish wedding of the Treasury Secretary’s daughter Christina that John and Jeremy – posing as brothers John and Jeremy Ryan, venture capitalists from New Hampshire – decide to pursue Christina’s sisters Claire and Gloria Cleary. For Jeremy, Gloria is just another potential conquest, but John is immediately enamored by Claire’s classic beauty and elegance.
Finding an actress to play the headstrong Claire proved to be a long journey that resulted in the casting of Rachel McAdams, who starred in last summer’s hit films The Notebook and Mean Girls.
“I never stop casting because if I cast the movie correctly, I’ve done half my job already,” says David Dobkin. “Hundreds of actresses auditioned for the role of Claire, but none of them really captured the essence of the character. I was an hour from going to the studio and presenting my top two choices when Rachel McAdams came into my office. I just loved her energy immediately. I threw her a couple of curve balls just to see how good she was and she nailed both of them, which made my decision really easy.”
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