The movie Leonardo DiCaprio was blackmailed into making: “I turned it down at least ten times”

Most young actors aren’t in the position to pick and choose which roles they play during the earliest years of their careers. Then again, not many young actors weren’t as preternaturally talented as Leonardo DiCaprio.

Two years after making his feature debut in 1991’s sloppy horror sequel Critters 3, DiCaprio was already being celebrated as one of his generation’s most promising and gifted young stars after his third movie role saw him hold his own against Robert De Niro in the aching drama This Boy’s Life.

His fourth film earned him an Academy Award nomination for ‘Best Supporting Actor’ in What’s Eating Gilbert Grape, and his fifth reiterated that he was no flash in the pan when he delivered another heart-wrenching performance in The Basketball Diaries.

When the latter was released, DiCaprio was still only 21 years old, and he had the world at his feet. Naturally, studio executives, producers, and filmmakers were falling over themselves to try to cast him in their latest production, which led to plenty of deliberation on the youngster’s part.

He’d never made an out-and-out genre flick at the time, which left him hesitant to accept a part in Sam Raimi’s western The Quick and the Dead. In fact, he repeatedly turned it down and showed little interest in playing ‘The Kid’ until he was given 24 hours to make up his mind before it went to another actor.

“I really had to think it through for a long time,” he told Movieline. “It was honestly not my idea of the type of movie that I wanted to do next. I turned it down at least ten to 20 times. Then on the last day, they said, ‘Hey, look, they really want you, and this is the last day you can have the role because they’re going to hire somebody else.'”

DiCaprio had been put on the spot, with the chance to work alongside a talented director and a heavyweight ensemble, ironically entering the last chance saloon. With the clock ticking down, his last-minute call was one that he didn’t end up regretting.

“I had this thing about not doing big commercial movies,” he reasoned. “Because all the big commercial movies, not all of them, but most of the mainstream movies are just pieces of garbage that have been done over thousands of times.”

He was swayed by the presence of leading actor and producer Sharon Stone, the venerated Gene Hackman, Russell Crowe, and The Evil Dead mastermind Raimi behind the camera. In his own words, “I thought, look, I’m not working. I could do something different, and I can have fun with this movie. Why not?”

Issuing ultimatums rarely yields the best results in Hollywood, but DiCaprio decided that being told The Quick and the Dead was a take-it-or-leave-it opportunity on the last day he would be under consideration for ‘The Kid’ was the right choice.

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