THE TOP FIVE

Gus Van Sant — Milk
A powerful return to form that will piggyback on the Prop 8 furor and channel Obama-esque enthusiasm about the country and its politics.

Jonathan Demme — Rachel Getting Married
He’s done it before, and he can do it again. Especially when he shows he’s not a one-trick pony.

David Fincher — The Curious Case of Benjamin Button
The mastery he displayed in grungy masterpieces Se7en and Fight Club, applied to a Gumpian narrative, could spell Oscar.

Danny Boyle — Slumdog Millionaire
A beautiful achievement made for “just” $13 million. In this field, that deserves recognition.

Christopher Nolan — The Dark Knight
The extent to which he legitimized the superhero movie as a bona fide segment of the American cannon canon deserves an award in itself.

THE TOP FIVE

Viola Davis— Doubt
She’s on for one scene, but what a scene.

Taraji P. Henson — The Curious Case of Benjamin Button
To play a character (in this case, Brad Pitt’s mom) who ages from 26 to 71 is to knock on Oscar’s door.

Penelope Cruz — Vicky Christina Barcelona
Being in a Woody Allen film is a good luck charm for supporting roles (Oscars have gone to Michael Caine, Mira Sorvino, and Dianne Wiest, twice!)

Marisa Tomei — The Wrestler
If there were ever any doubts that she deserved her Oscar for My Cousin Vinny, her heartbreaking, topless turn as an over-the-hill stripper should put them to rest.

Rosemarie DeWitt — Rachel Getting Married
In the titular role, she could get a nod if Anne Hathaway does.

Heath Ledger—The Dark Knight
That he will win is about as certain as the fact that the actor, gone far too soon, will close out the "dearly departed" segment to thunderous applause; Hollywood loves a good story, which a posthumous Oscar qualifies as. He would be the second actor to win one, after Network’s Peter Finch.

Michael Sheen — Frost/Nixon
He was brilliant in The Queen, and more than holds his own against Langella’s imposing Nixon as the out-of-his-league British newscaster who took on Tricky Dick and won.

Michael Shannon — Revolutionary Road
Gobbles the scenery as the schizophrenic neighbor who speaks the truth, a performance that will surely help him put Kangaroo Jack behind him.

Robert Downey Jr. — Tropic Thunder
Nominating him for his off-the-wall impression of Russell Crowe as a black man would prove the Academy has a sense of humor, but more importantly, would acknowledge the extent to which Downey has jolted Hollywood in the past year. His consolation prize his work in the unOscarable Iron Man was supposed to have been for The Soloist, but that was pushed back to 2009.

Philip Seymour Hoffman — Doubt
A nomination for his ambiguous performance as priest with ambiguous motives would be deserved, but unsurprising and, in the end, unexciting. Still, never count this Oscar machine out.

Meryl Streep — Doubt
She hasn’t won Best Actress since Sophie’s Choice, but she’s almost systematically nominated. There is no reason she won’t be tapped again for her performance as a nun wracked with suspicion, the Miranda Priestly of the convent, as it were.

Kate Winslet —Revolutionary Road
Winslet, the youngest actress in history to receive five nominations, will almost certainly get her sixth for Revolutionary Road, and is very likely to get a seventh for The Reader as well (albeit in the Supporting category). The Academy is sure to be receptive to her honesty, when she told this magazine: “Yes, I want an Oscar!”

Kristin Scott Thomas — I’ve Loved You So Long
Her performance as a mother who killed her 6-year-old son (so French!) would be a shoe-in for an Oscar if it wasn't in...French. But that didn’t stop Marion Cotillard last year.

Angelina Jolie — Changeling
The movie was overlooked, and will probably be eclipsed by Eastwood's newer, fresher, harder-hitting Gran Torino. Plus, she wasn’t nominated for her previous : The Good Shepherd and A Mighty Heart. Still, Eastwood's movies regularly attract acting nods.

Anne Hathaway — Rachel Getting Married
She’s good enough, she’s pretty enough, and gosh darn it, people like her.

THE TOP FIVE

Sean Penn — Milk

This is the first time we’ve seen Sean Penn smile since he played Jeff Spicoli (with the possible exception of I Am Sam). The second could very well be at the Kodak theater, when the current frontrunner takes home the trophy for his masterful performance as a gay politician turned martyr.

Mickey Rourke — The Wrestler

The 52-year-old comeback kid was considered a lock from the get-go for his heartbreaking turn as an aging professional wrestler. It’s possible for such advanced buzz to last until the envelope is opened (see Daniel Day-Lewis), but it’s more likely Rourke will piss a bunch of people off before that.

Clint Eastwood — Gran Torino

Eastwood’s never won an Oscar for acting, and he looks pretty badass in the trailer (which is all we can judge on for now). But does a man with four Oscars need a consolation prize? Since the 78-year-old has hinted this would be his last leading role, it’s quite possible. One more time, with feeling: “never bet against Clint Eastwood.”

Richard Jenkins — The Visitor

As a crotchety middle-aged professor forced to loosen up, Richard Jenkins shows how refreshing a character actor can be in a leading role. That feat—combined with Hollywood's good will towards hardworking pros— could earn him a nomination, but unfortunately not a win.

Leonardo DiCaprio — Revolutionary Road

He’s been one of his generation’s best actors for half a generation but hasn’t yet been recognized, despite three nominations. Depends whether the film pleases the Academy as much as it clearly aspires to.

THE TOP FIVE

Slumdog Millionaire
A beautifully woven tapestry—from an acclaimed but as-yet unrewarded director—about fate, true love, and the power of internationally franchised quiz shows to overcome devastating Third-World poverty. Could be this year’s Little Miss Sunshine, especially considering its sold-out opening weekend. In the last few days, it has recently become the film to beat.

The Curious Case of Benjamin Button
Brad Pitt ages in reverse in this adaptation of a sweeping F. Scott Fitzgerald fable. The presence of Forrest Gump writer Eric Roth, and Fight Club director David Fincher in a thematic departure make it the current frontrunner, but leaked reviews have deflated its sails a bit in the past week. Jury’s out till it’s released.

Frost/Nixon
A movie based on a play about an interview is not typical Oscar fodder, but considering the arsenal of talent behind it—namely Oscar darling Ron Howard, Tony winner Frank Langella, the inimitable Tony Blair Michael Sheen, and a script by The Queen playwright Peter Morgan—it stands a good chance.

Milk 
Buoyed by Sean Penn’s transformative performance, this story of the martyred, openly gay San Francisco politician Harvey Milk seems especially timely amidst Hollywood’s outrage over the passage of Proposition 8. Will that last until February, with an Academy that passed up Brokeback Mountain for Crash?

Revolutionary Road
Leonardo DiCaprio and Kate Winslet reunite as a struggling couple in this 60s period piece adapted from a critically acclaimed novel. It’s directed by Winslet’s husband, Sam Mendes, whose last domestic drama, American Beauty, won Best Picture. So it’s got that going for it. It could also piggyback off the popularity of TV’s Kennedy-era show Mad Men. It's a clear grab for gold, but according to early reviews, it may overreach.