Sean Penn is a serious man. Every now and again we’ll get a glimpse of how serious he can be even in the midst of comedic settings, like that year at the Oscars when he condescendingly mansplained to host Chris Rock who Jude Law is. His seriousness can make him hard to be publicly at times. But it’s also likely the primary contributing factor to just how devastatingly good he is at acting.
He was first introduced to a large audience in the 1982 comedy Fast Times at Ridgemont High as the iconic character Spicoli, but since then he has evolved into an actor who can play a variety of characters ranging from stoned surfer to hardened death row inmate. He’s also shown a propensity for picking interesting projects to be a part of, a sign of an actor who’s as sharp as he is talented. His contributions to movies of Terence Malick is particularly admirable, even if he isn’t always happy with the end results. More recently, he’s shown his talent behind the camera, directing the critically beloved Into the Wild. Unlike Ben Affleck though, he’s too good of an actor for anyone hopes he gives that up in favor of directing.
There are 5 pivotal roles that transformed Sean Penn from solid supporting actor to one of the most reliable and electric leads of his generation. It’s interesting to see how he’s progressed as an actor, seeming to improve with each performance, right up to his best work in his most recent Oscar-recognized film.
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