Sean Penn

Penn was a professional as a teenager: Taps at twenty-one, then Fast Times at Ridgemont High, where Jeff Spicoli made him a comic star he then spent fifteen years refusing to be. The 1980s work reads like a deliberate escape route, all of it hard and most of it violent, through Bad Boys, At Close Range, Colors and Casualties of War.

The thing he does is compression. Penn does not play emotion outward; he plays a man holding something down until the effort itself becomes the performance, which is why his best work is nearly always about grief or guilt. Mystic River and Milk won him Academy Awards for Best Actor, and in 2025 he took Best Supporting Actor for One Battle After Another, with earlier nominations for Dead Man Walking, Sweet and Lowdown and I Am Sam.

That intensity is also his liability. Penn can be enormously heavy, and when the material is already heavy the effect doubles: 21 Grams and The Last Face are exhausting for reasons that are not entirely the films' fault. He is better with a director who will not let him settle, which is why the Fincher, Malick and De Palma appearances are worth more than their running time.

Directing has been the parallel career, from The Crossing Guard through The Pledge to Into the Wild, which is the best of them and the one where his appetite for suffering finds a subject that earns it. Late comedy has been the surprise. Licorice Pizza and One Battle After Another both use him as a vain, sozzled monument to himself, and he is extremely funny in both. He received an Honorary Cesar in 2015 and the Bob Hope Humanitarian Award in 2022.