Image: Johnny Depp and Angelina Jolie in "The Tourist"
Sony Pictures  /  Reuters
Johnny Depp and Angelina Jolie star in the thriller "The Tourist." The December release was bankrolled by Tim Headington, who has also backed the Oscar-winning "The Aviator."
updated 12/17/2010 7:56:50 AM ET 2010-12-17T12:56:50

Two billionaires are going head to head in a box office battle this month. Philip Anschutz's "The Chronicles of Narnia: The Voyage of the Dawn Treader" is facing off against Tim Headington and his Johnny Depp/Angelina Jolie thriller "The Tourist."

It is not the first time these billionaires have made big Hollywood bets. The two tycoons have plenty of company. Dozens of billionaires have spent excess cash funding the risky but sometimes glamorous business of Hollywood films. Some have scored big returns; others bankrolled flops.

Tim Headington has experienced both. Headington, who sold a piece of his family's stake in North Dakota's Bakken shale to XTO Energy for $1.8 billion and has a personal net worth of $2.65 billion, has backed two Martin Scorsese/Leonardo DiCaprio hits: "The Aviator" (five Oscars) and "The Departed" (four Oscars, including Best Picture).

But Headington experienced bad timing with "The Edge of Darkness," featuring beleaguered star Mel Gibson. That film grossed just $80 million on a budget of $80 million. He'll get another shot for box office bullion with "The Tourist." His other Depp film, "The Rum Diaries," is set to debut in 2011. slide show: Billionaires bet on the box office

Anschutz, who ranks 34th on the 2010 Forbes 400 list with a net worth of $7 billion, earned a Best Picture Oscar for the Jamie Foxx hit "Ray." The Ray Charles biopic was a departure from the family-friendly flicks often produced by Anschutz' Walden Media. Besides the Narnia franchise, Anschutz has backed tame films like "Holes," "Hoot" and "The Tooth Fairy." Anschutz' fortune stems from investments in the railroad business, fiber optics (with Qwest Communications) and entertainment venues through AEG, which controls 120 sports and entertainment venues, including the Staples Center in Los Angeles.

EBay billionaire and former president Jeff Skoll usually produces films with a social message. His company, Participant Media, funded Al Gore's climate change documentary "An Inconvenient Truth." That film won an Oscar for Best Documentary and helped Gore score the Nobel Peace Prize. Other influential films include "Food Inc." and "Waiting for Superman."

He had less luck with the clumsy comedy "Furry Vengeance," about forest critters getting revenge on a land developer. That movie cost $35 million and grossed $36 million. Skoll, a Canadian who no longer works for eBay, has a net worth of $2.4 billion on Forbes' 2010 World's Billionaires list. 25 multimillionaires without high school diplomas 13 supermodels turned moguls 10 celebrity-backed startups

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