Sean Penn

2025 · Paul Thomas Anderson · 161 min · Drama / Thriller

One Battle After Another is Paul Thomas Anderson finally aiming his full powers at a chase movie, and the collision produces the most acclaimed American film of its year. Leonardo DiCaprio plays a burned-out ex-revolutionary in a bathrobe who must remember sixteen years of forgotten tradecraft when his daughter is hunted by the deranged colonel from his past, played with career-peak menace by Sean Penn. It's funny, furious, and staged with a rolling-hills car chase already being called one of the greatest ever filmed. The politics run hot and the length runs long, and neither slowed its momentum toward instant-classic status.

2003 · Clint Eastwood · 138 min · Crime Drama

A devastating crime drama powered by career-defining performances from Sean Penn and Tim Robbins, exploring how childhood trauma ripples through decades and destroys lives with the force of a Greek tragedy.

1982 · Amy Heckerling · 90 min · Comedy

A raunchier, messier precursor to the polished teen comedies that followed, memorable primarily for Sean Penn's iconic Spicoli and a willingness to treat its teenage characters as messy, complicated people.