The Essential Sean Penn: The Roles That Defined the "Milk" Star

By |

It's no secret why Sean Penn is the leading actor of his generation. His talent is right up there on screen, blazing so bright that you can't miss it. That's what makes him the frontrunner for this year's Best Actor Oscar for Milk, in which his performance as the assassinated gay rights activist Harvey Milk is an act of total character immersion. In the Rolling Stone cover story, Penn talks about the importance of committing to a role, taking a shot at actors who put more energy into selling themselves as products than putting in the necessary work it takes to build a performance.

Has Penn ever sucked? You bet. Try Shanghai Surprise, the 1986 laugh-free farce he did with his ex-wife Madonna. Or All the King's Men, the 2006 political drama that takes risks that just don't pay off. It's always been my theory that no actor can be truly great unless he or she risks falling on their ass. Look at Brando. Look at Streep. Penn belongs in that classy company.

Watch him take the screen as if by divine right in his first major screen role in 1981's Taps, costarring with Tom Cruise (whatever happened to him?) as a cadet in a military school about to start his own revolution.

Of course, for most of us the breakout Sean Penn performance came a year later in Fast Times At Ridgemont High, playing Jeff Spicoli, the surfer dude who thought nothing of ordering pizza to be delivered to his history class. For Spicoli, life was all about "a cool buzz and some tasty waves." Penn was tasty comic perfection.

Students of Penn's career know that comedy was not the area he pursued. Look at the movies that won him Oscar nominations as Best Actor — the murderer on death row in Dead Man Walking, the haunted jazz guitarist in Woody Allen's Sweet and Lowdown, the mentally challenged father in I Am Sam (a role tweaked for laughs by Robert Downey, Jr. in Tropic Thunder), and the parent of the murdered girl in Mystic River, which won him the prize in 2004. Now, with Milk, Penn is on the verge of collecting well-deserved Oscar bookends. Other Penn performances in such films as At Close Range, The Falcon and the Snowman, Casualties of War and Carlito's Way, hold a place of honor in my personal Penn pantheon, as does his directing talent, seen in The Indian Runner, The Crossing Guard, The Pledge and 2007's magnificent Into the Wild.

Cut your own path through Penn's career and I'm sure you'll come up with your own favorites. At 48, Penn shows the talent and spirit of an actor and filmmaker who's still spoiling to heard.