National All or Nothing Day: Celebrate the Times John Wayne, Clint Eastwood and Other Western Stars Risked It All

by Matthew Wilson

John Wayne, Clint Eastwood, Kevin Costner – they’re some of the biggest names in not just the western genre but all of Hollywood. Through their characters, they taught viewers how to be tough as iron and never to back down. But in real life, these western stars had to dig deep at different moments in their career to put it all out on the line.

Win or fail, it’s the trying that matters. And in honor of National All or Nothing Day, Outsider is looking back at the moments these western greats aimed for the stars. They may have ended up with their face in the dirt. But no cowboy ever got things done without getting a little dirty in the process.

Take John Wayne for instance. He was the cowboy. When most people close their eyes, they picture John Wayne riding across some sunlit prairie. But in real life, Wayne bet his entire fortune and reputation as an actor on his dream project. For years, the Duke dreamed of making a western adaptation of one of history’s most remembered last stands – The Alamo.

For the project, Wayne ended up investing his own money. He put out mortgages on his house, his cars, even his New York apartments. The actor leveraged every connection he made in Hollywood during his career to get the movie made. It cost $12 million to make Wayne once said, “I mortgaged everything I own in this picture, except my necktie.”

Wayne ended up directing the film himself, through an admittedly cursed production. For his trouble, the film ended up grossing $20 million at the box office. But many fans remember the film as a classic and Davy Crocket as one of Wayne’s signature roles.

Clint Eastwood Takes A Gamble On A Spaghetti Western

The “Dollars” Trilogy is one of Clint Eastwood’s most iconic works. But the actor took a gamble on “Fistful of Dollars” early in his career. At the time, Eastwood had made a name for himself, starring as Rowdy Yates on the western series “Rawhide.”

But as an actor, he longed for something else. That’s when Eastwood got wind that a small Italian director was filming a Spaghetti western. Eastwood would have to go abroad to film the movie, which paid $15,000 for 11 weeks

“In ‘Rawhide’ I did get awfully tired of playing the conventional white hat. The hero who kisses old ladies and dogs and was kind to everybody. I decided it was time to be an antihero,” Eastwood said.

It ended up being one of Eastwood’s greatest career choices he ever made. After the film blew up, Eastwood became a bonafide movie star, helping to create an entire genre of anti-hero cowboys and later detectives. Eastwood’s entire Hollywood venture started with that move.

‘Yellowstone’ Star’s Film Sinks Under Costs

Before he was every “Yellowstone” fan’s John Dutton, Kevin Costner made a name for himself in films. But one passion project almost sank his career. “Waterworld” ended up being one of the most expensive movies ever put to film. In fact, when the movie went over budget, Costner put reportedly $22 million of his own money to finish the picture.

With a budget of $175 million, the film ended up a box office disappointment in the U.S. But worldwide, it made $264.2 million, recouping Costner’s loss. While hardly a success, Costner walked away relatively unscathed to star as John Dutton in the hit western series “Yellowstone.”