Sean Penn Says His Cocky Attitude Almost Cost Him Breakout Role In 'Fast Times At Ridgemont High'

Sean Penn said his feeling of entitlement almost cost him his breakout role in the 1982 teen comedy film, Fast Times at Ridgemont High.

During a virtual appearance on the Tonight Show Featuring Jimmy Fallon, the Oscar-winning actor, 59, admitted that even before he was a star, he carried around a sense of entitlement when he went on auditions. Penn told Fallon that long before he had "a penny" in his pocket, he had a feeling of entitlement as an actor, not because he thought he was so good, but because he thought everyone else wasn't so good.

"And that gave me a lot of confidence," he explained.

Penn said he "resented" every audition he went to and ended up doing a "terrible" read for the part of Jeff Spicoli in Fast Times at Ridgemont High.

"I just wanted them to just give it to me," the actor admitted. "But I auditioned — and terribly and flat — and I knew I wasn't willing to hit the music of this character I thought it was and had familiarity with too. I'd grown up with a lot of people like that."

Penn revealed that he only landed the iconic role of the stoner high school student in the Amy Heckerling film because a casting director named Don Phillips saw his potential even after his awful audition.

"Don Phillips came running into the parking lot, where my broken down Mazda I borrowed was sitting, and I was just about to leave and he said, 'Get back in here and audition you're a** off…You're not going anywhere.'"

Penn said he went back in and gave more to the audition. He ended up having a "great time" making the movie, which also starred Judge Reinhold, Jennifer Jason Leigh, and Phoebe Cates and featured brief appearances by then-unknowns Nicolas Cage and Forest Whitaker.

Once Penn scored the role, he threw himself fully into it. Screenwriter Cameron Crowe, whose real-life experiences inspired the movie, revealed that Penn wore his character's black-and-white checkerboard shoes every day on set and refused to let anyone call him by his real name.

"He didn't let us call him by his name until the last day when he gave Amy [Heckerling], Art [Linson, the producer], and I each a ceremonial shoe and said, 'My name is Sean,'" Crowe told Vanity Fair.

Before Fast Times at Ridgemont High, Penn only had a few acting credits with guest roles on TV shows like Barnaby Jones and Little House on the Prairie. He made his film debut in the 1981 film, Taps.