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

Illustration by: Louise Pomeroy

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

This story first appeared in the Nov. 28 issue of The Hollywood Reporter magazine.

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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Then everything changed. Universal shifted Cinderella's release to the following year, while Warner Bros., sniffing an opportunity, plopped Clint Eastwood's Million Dollar Baby into the race.

Before it screened, the picture had been referred to derisively as "the female Rocky." Insiders were scratching their heads about why Eastwood would ever want to make a film about boxing, let alone with a seeming one-shot-wonder named Hilary Swank, thus far distinguished only by Boys Don't Cry five years earlier, as a young woman who enlists a reluctant coach to make her a champ.

The movie had missed all the major festivals, but then it played to a small, private audience at Warners' Steven J. Ross Theater, and soon it caught fire. Months later, it won statuettes for Swank and Morgan Freeman, and allowed Eastwood to add two Oscars to his brace for 1992's Unforgiven.

Now the Great Disrupter is back with American Sniper.

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Like Million Dollar Baby, American Sniper was shot and released in the same year; like the former, it missed most major festivals (before debuting at AFI Fest on Nov. 11); and like Million Dollar, it's a late entry that could be a game changer. But will that be enough to get it past the finish line?

Sniper had a mixed response at AFI, where it wasn't helped by screening right after Paramount's Selma (about the 1965 civil rights march led by Martin Luther King Jr.). Insiders say Warners initially had believed only about 30 minutes of Selma would be shown; having two heavy real-life dramas screen back-to-back diminished both and left insiders debating which had emerged the stronger contender.

Warners also might have a problem with star Bradley Cooper's availability: He's doing The Elephant Man on Broadway, though the studio says he still will be active and involved in the campaign from New York.

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More important, Sniper's point of view fits less comfortably with the liberal-leaning Academy than Eastwood's two previous best picture winners — one a paean against violence (Unforgiven), the other an elegy about boxing (Million Dollar). This movie celebrates real-life Iraq War hero Chris Kyle (Cooper), who had more killings than any other soldier.

"They'd have to change the logic of the entire votership because these red-state, red-bait movies have got to appeal to L.A. and New York — and that's going to be tough," says one rival awards campaigner. "This lefty crowd isn't going to gather around a Navy SEAL best known for killing people."

So can Sniper still win? Yes, and here's how:

First, its immediate goal must be to become one of the five to 10 movies nominated for best picture. In a weak year, that should be easy. Warners has to stress Eastwood's iconic stature; remind voters that his age (84) means he won't have that many more shots at an Oscar; and note that he particularly avoided going for the type of all-out violence that may have marred the chances of another recent war movie, Lone Survivor.

Second, they should make Sniper part of the current debate on sending forces back to Iraq to take on the Islamic State. The movie shows the price one war hero paid; do we want other heroes killed, too?

Third, get endorsements — not from the obvious, the Colin Powells or military vets who will only alienate the Academy, but from war activists who see Kyle's life as a lesson for others.

All this will help. But only one thing can close the deal: Clint himself.

True, he stuck his foot in it at the 2012 Republican convention, but there are few figures in Hollywood more admired than he is — by the right and left.

No movie in this year's race has provided voters a compelling reason to name it best picture. Clint gives them that reason. But Warners has to persuade the famously reticent star to get out there. Get Clint talking, and he just could win this war.