High Anxiety

Sure, the new year is hardly two weeks old, but it's never too early to guess what the next 351 days will bring for stars at crucial moments in their careers. Who, for example, could have guessed last January that Courtney Love would be arrested for beaning an NYC concertgoer in the head with a mic stand? (Okay, we had that covered.) With such surprise developments in mind, EW looks at this year's riskiest celebrity gambles.

Brad Pitt and Jennifer Aniston
Not-so-happy New Year! On Jan. 7, Pitt and Aniston announced their separation, creating a few problems: The future of their Plan B Entertainment — which lost partner Brad Grey, who just left to become the head of Paramount Pictures — is in flux. They've both got to promote movies (her Graduate-inspired Rumor Has It opens later this year; his spy caper Mr. and Mrs. Smith, costarring Angelina Jolie, arrives June 10). And, oh yeah, Nick and Jessica are now America's premier power couple. ''I wouldn't be surprised if Plan B continues, and Brad brings in another partner,'' says one top Hollywood manager of the production company behind the upcoming Charlie and the Chocolate Factory. ''It's a brand that means something — one of the few talent-driven production companies that's legit.'' As for those unsubstantiated tales of a Pitt/Jolie tryst, such rumors didn't help the Russell Crowe/Meg Ryan dud Proof of Life. If nothing else, says the manager, ''it will get journalists writing more about the movie than they would have before.'' Guilty as charged!

Cameron Diaz
The ebullient star is due for a comeback — and certainly needs one to warrant that $20 million paycheck. In Her Shoes (out April 8), based on Jennifer Weiner's best-selling chick-lit novel about party girl Maggie Feller (Diaz) and her straight-edge sister, Rose (Toni Collette), could be just the ticket. ''Some of the more overtly commercial stuff she's done hasn't let her stretch emotionally,'' says Fox 2000 Pictures president Elizabeth Gabler. ''The strength of this film is the material. It's darker.'' Hmm...Cameron Diaz + dark material = ...heck, maybe another gem like Something About Mary! Anyway, it can't be worse than The Sweetest Thing.

Ben Affleck
''Think about John Travolta in Pulp Fiction,'' says a producer who wonders if Affleck's next part — as a slick Hollywood agent cuckolded by his wife (Rebecca Romijn) in the dramedy Man About Town — is enough to reestablish his long-gone cred. ''Actors who've fallen out of audiences' good graces need to pick smaller parts that surprise people. Ben reached a place where he cost so much that there were only certain movies that could afford him...and those movies are probably the ones that aren't so good.'' We know. We've sat through them.

Ashlee Simpson
It's a one-two punch for the media's whipping girl: Her MTV reality show returns Jan. 26, just weeks before she (eek!) kicks off a 27-city tour in Anaheim, Calif. The show's producer, Rod Aissa — who caught Simpson's post-hoedown reaction at SNL on camera — was disturbed by the fuss over her subsequent Orange Bowl debacle, which prompted one newspaper to ask ''Why Is This Woman Still a Star?'' ''I don't think that was fair,'' says Aissa. ''Other performers screw up without our questioning whether they should still be a star. It's all about what we buy into and how they strike a chord. And our audience still loves Ashlee — no matter what.'' He better hope so.

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