'Grey's Anatomy' Star Patrick Dempsey Tests His Movie Stardom

During his writers'-strike-induced hiatus from "Grey's Anatomy," which returns with new episodes Thursday (ABC, 9 p.m. ET/PT), Patrick Dempsey whisked wife Jill away for a romantic Italian getaway. No kids. No cameras. And no reporters.

The couple, married since 1999, took in a fashion show in Milan; then, in Lake Como, they were among many marveling at the waterfront estate of that city's most famous resident: George Clooney.

"He's larger than life," says Dempsey. "I've met him a few times now, and he has always been very funny and charming. I like him."

Though he'd perhaps prefer comparisons with his idol, Cary Grant, it is Clooney with whom Dempsey has been compared ever since he rejuvenated a stalled teeny-bopper career by hitting it big on a prime-time medical series. Clooney, of course, did the same when he segued from early "Facts of Life" fodder to "ER" superstardom.

With his comedy "Made of Honor" hitting theaters May 2 and potentially solidifying his movie stardom for the first time since his late '80s hits -- "Can't Buy Me Love" (as a dorky kid who hires a cheerleader to be his girlfriend) and "Loverboy" (as a pizza delivery boy who delivered a little something extra to desperate housewives) -- the Clooney comparisons are back.

Dempsey, 42, got an early jump on his leading-man status last year by wooing princess Amy Adams away from the charming James Marsden in "Enchanted." Its almost $128 million domestic take has producers dreaming up a sequel. But "Enchanted" was an ensemble.

"This is the first time I've carried a movie in a long time," Dempsey says over drinks at a corner table in the Four Seasons Hotel bar. As a result, he has been asking himself, "Can I pull this off? Will people come see it?"

"This is a very big film for him," says "Made of Honor" director Paul Weiland. "Patrick grew up in the (Hollywood) system, but I'm not sure he wants to stay in it forever."

Dempsey concedes that he "wasn't sure if 'Enchanted' was going to work." So he sought another project that would be "light and different from 'Grey's'. And with a broad-based appeal. Something that would do well commercially to allow me to cross over."

In the movie, Dempsey plays Tom, who realizes he's fallen for his best friend since college, Hannah (Michelle Monaghan). But just as he's ready to tell her, she announces her engagement to a European man she only just met. Tom decides to pursue the girl of his dreams before he loses her forever. The problem: She has asked him to be her maid of honor. Uh-oh.

His life is a circus

Seasoned to addressing those old Clooney analogies, Dempsey is now having to face his new film's similarities to 1997's "My Best Friend's Wedding," which found Julia Roberts in a similar scenario -- sabotaging the wedding of her own best friend, with whom she had unexpectedly fallen in love. To distance his character from Roberts' unlikable schemer, Dempsey committed himself to making Tom redeemable. Scenes were tweaked to make the character more comical.

No problem for Dempsey, who once applied to Ringling Bros. and Barnum & Bailey clown college. He remembers filling out the questionnaire, which he says posed such quirky queries as, "How do you feel about small spaces?"

"But I was 17 and you had to be 18, and I didn't get in," he says, still seeming a bit stung.

Diploma or not, "clown" is the first word Weiland uses to describe his leading man.

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