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Sean Penn as Jeffrey "Jeff" Spicoli

Penn's initial audition for the movie went terribly. "Long before I had a penny in my pocket, I had a kind of feeling of entitlement as an actor, not because I thought I was so good, but because I thought that the rest were not so good," he told Jimmy Fallon during a previous appearance on The Tonight Show. Luckily, he got a second chance and won the part.

Image Source: Everett Collection