The List: Hollywood’s funniest prettyboys

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From the March 15, 2012 edition

With Hollywood hunk Channing Tatum showing his comedy side in “21 Jump Street,” we’re counting down 10 leading men who prove you can be both handsome and unexpectedly hilarious.

10. Justin Timberlake

Who would’ve thought the pretty boy from the prettiest boy band would turn out to be one of the funniest guests to be on “Saturday Night Live” has had in recent years? He’s moved on to movies but hasn’t yet found one that’s showcased how funny he can be.

9. Ryan Gosling

He made everyone cry in “Blue Valentine.” He took intensity to a new level in “Drive.” But his deadpan humor in “Crazy, Stupid, Love.” and “Lars and the Real Girl” was enough to make the ladies forget about that six-pack … for a second.

8. Johnny Depp

Depp’s had heartthrob status since the original “21 Jump Street,” but he’s always had a funny streak, particularly the physical comedy of his best known character, Captain Jack Sparrow.

7. Matt Damon

Paul Rudd’s “40-Year-Old Virgin” character thought Damon was “kind of a Streisand,” but it turns out he’s pretty badass funny in the “Ocean’s” trilogy and “True Grit.” His guest role on “30 Rock” as Liz Lemon’s neurotic airplane pilot was pretty great, too.

6. Paul Newman

He’s starred in some of the most respected films of all time, but Newman also made us laugh heartily in “Cool Hand Luke,” “Butch Cassidy and the Sundance Kid” and especially “Slap Shot.”

5. James Franco

He was brooding, handsome and pretty funny in his debut on TV’s “Freaks & Geeks” and was a scene-stealing dope dealer in “Pineapple Express.” He also knows how to pick fun at his own handsome actor status, as in this parody of his Gucci ad.

4. Jon Hamm

As he has brooded his way through four seasons as Don Draper on “Mad Men,” there was hardly any hint of a sense of humor, but his appearances on “SNL,” “30 Rock” and in “Bridesmaids” show he’s got the chops to go full comedy if he wants.

3. Mark Wahlberg

The former rapper/underwear model hasn’t gone funny often, but when he does, he nails it, as in the absurdist ensemble comedy “I Heart Huckabees” or “The Other Guys,” where he was actually funnier than Will Ferrell.

2. George Clooney

The perennial Oscar nominee is often overlooked for his outstanding comedic range — the abstract-thinking country bumpkin in “O Brother, Where Art Thou?” the cool, smooth-talker in the “Ocean’s” trilogy and “Up In the Air,” and even the Jedi psychic in “The Men Who Stare at Goats.”

1. Brad Pitt

Ever since he took his shirt off in “Thelma & Louise,” he’s been considered one of the sexiest men alive. But he’s also effortlessly funny in the “Ocean’s” movies and downright goofy and hysterical in “Burn After Reading.”