By Jeff Labrecque
Updated April 25, 2012 at 06:38 PM EDT
Everett Collecton

When the conversation arises about the best comic actors who’ve successfully made the leap to serious roles, the names of Tom Hanks, Robin Williams, and Bill Murray are frequently mentioned. Rarely does anyone mention Sean Penn. The two-time Oscar winner, of course, is best known for playing gritty, emotionally turbulent anti-heroes, but it’s worth noting that his breakout Hollywood role was one Jeff Spicoli, the funniest wave-craving dude from Fast Times at Ridgemont High.

And it wasn’t a fluke. Over the years, Penn has proven to be a talented comedic thesp who can get both high- and low-brow laughs. Look no further than Woody Allen’s Sweet and Lowdown, where Penn was magnificent as the self-important jazz musician doomed to obscurity. So I was thrilled to confirm a Deadline report that Penn is in talks to costar opposite Ben Stiller in the remake of The Secret Life of Walter Mitty. Even if it’s a small role, it’s refreshing to see Penn flex these muscles. At the very least, he can get easy laughs by playing off his public persona — which includes being a curmudgeon as well as a devoted activist for humanitarian and liberal causes — but I hope he leaves that baggage at the studio gate and digs deeper. Because he’s not just one of the most talented actors around; he can also be one of the funniest. Take a look at some of his best comic moments over the years.

Fast Times at Ridgemont High

We’re No Angels

Sweet and Lowdown

Between Two Ferns

Do you often forget about Penn’s comic chops? Would you like to see him play funny again, or has his public and professional persona made it difficult for him to go back to lighter roles?

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