It ain't easy being cool in Hollywood. With so much pressure to create, maintain and sell an image, it's a wonder there are any cool cats left in showbiz (more on them later). After all, many stars rely on teams of publicists and managers to tell them how to dress and behave. On top of all that, many celebs are surrounded by a cocoon of "yes" people who constantly tell them how great they are -- making it pretty tough to stay down-to-earth.

Take, for example, Stephen Dorff. Once upon a time, he was one of the coolest Hollywood actors around. In the late '90s, he already had a string of undeniably cool movies on his resume, including I Shot Andy Warhol, Cecil B. Demented and Blade.

And then he did a Britney Spears video, for her song 'Everytime.' Is there any coming back from being the hunk in a Britney Spears video? It's a decidedly cheesy move, and it didn't even appear to be tongue-in-cheek. It was an earnest Britney Spears video with an underlying message about the perils of fame. Apres Britney, Dorff fell off the map for quite some time. Sure, he was still working. But he largely flew under the radar, until he started slowly building buzz again after starring as a lonely rock star in Sofia Coppola's Somewhere two years ago. Dorff has even credited Coppola with making him cool again.

The question is: can an actor get his cool factor back? I'd like to believe it's possible, since Dorff was so cool back in the day. He's certainly very gracious and humble about the Britney video, which doesn't hurt his cool cred. Maybe this week's release, Brake, will be another step back in the right direction. Dorff headlines the action/thriller as a Secret Service agent held captive in the trunk of a car.

Dorff just might be able to find his cool again. It's not like he's done something unforgivably ridiculous, a la his once-cool contemporary Jared Leto, whose constant parade of douchey shenanigans have tarnished any Jordan Catalano halo effect he once coasted on. And Dorff still has his original face, unlike former cool guy Mickey Rourke. Some might argue that Mickey is still cool -- I would counter that you can't have that much plastic surgery and maintain your street cred.

But this blog isn't all about hatin'. There are a handful of celebs who have managed to stay cool after all these years in the biz, choosing (mostly) projects they care about, staying committed to their craft and, by all reports, remaining more-than-decent human beings. With that in mind, I've compiled an undeniably nerdy list of the top five celebrities who have grown even cooler with age.

1. Jeff Bridges The dude abides, man. Even when he's voicing cute animated penguins like Big Z in Surf's Up, Bridges maintains his cool factor. You'd be hard-pressed to find anyone with a cooler resume. From The Big Lebowski to True Grit to Crazy Heart and even nerd-fave TRON, Bridges always oozes an effortless, laidback charm.

2. Johnny Depp Johnny proved that it's possible to star in a Disney franchise without losing your cool. In fact, his turn as the uber-suave Captain Jack Sparrow in the Pirates of the Caribbean movies made the former bad boy even cooler, with his uncanny ability to channel the King of Cool, rock God Keith Richards.

3. Milla Jovovich Model-turned-actress Milla has been radiating cool since the '80s, when she first started strutting her stuff for high-profile fashion photographers like Herb Ritts. She beefed up her cool credentials in 1993 cult classic Dazed and Confused, which she followed up with more smart choices like The Fifth Element and, of course, the entire Resident Evil franchise.

4. Anjelica Huston At 60 years old, Anjelica is still pulling off her signature long dark locks and a rock star wardrobe. After over three decades in Hollywood, she has stayed true to herself. Anjelica ain't conformin' for nobody! And that's why we love her so. Her turn on fan-favorite TV show Smash is certainly helping matters.

5. Ewan McGregor I almost gave Christopher Walken this fifth spot, but then I saw Ewan on Conan, oozing cool and suavely inviting Louis C.K. to "put his money where his mouth is." 16 years after Trainspotting, Mr. McGregor has still got it.

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A federal agent (Stephen Dorff) is taken captive by terrorists who want to know the location of the U.S.... Read More

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