Clint Eastwood's Oscars Challenge: Getting Liberal Voters to Love 'American Sniper'

With his late-entry contender, the legend may pull off another 'Million Dollar Baby,' but he's got some work to do: "This lefty crowd isn't going to gather around a Navy SEAL best known for killing people," says a rival campaigner

Deep into 2004, as the Oscar race was coalescing around just a few pictures, Martin Scorsese's The Aviator looked like the film to beat. It was classy, it was a period piece, it had a roster of top-notch performances, it was directed by America's most acclaimed filmmaker and its subject matter was near and dear to Hollywood's heart: Howard Hughes.

Sure, Alexander Payne's Sideways and the biopic Ray looked like they might give it a run for its money. But both were small in scale, unlikely to appeal to below-the-line voters, and had none of Aviator's scope.

Just one small threat loomed on the horizon: a boxing picture helmed by an Oscar-winning director and starring an Oscar-winning actor. No, it wasn't the one you might think: It was Cinderella Man, based on the real-life story of James Braddock, which teamed Ron Howard and Russell Crowe for the first time since A Beautiful Mind.

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