On August 17, 1960, in Santa Monica, California, a future award-winning star entered the world — though nobody could have known it at the time. With both parents deeply rooted in theatre and acting, Sean Penn was practically destined to find his calling in film, both in front of and behind the camera. His older brother pursued a career in music, while his younger brother followed a path into acting.

What first ignited Penn's passion for the craft was making short films during childhood alongside his friends, among them Charlie Sheen and Emilio Estevez, who happened to live nearby. His earliest on-screen moment came as an extra on an episode of the television series Little House on the Prairie — a gig that was directed by none other than his own father.

In 1981, Penn made his film debut with an action drama production called Taps. He followed that up the very next year with a role in Fast Times at Ridgemont High, a beloved comedy widely credited with helping to popularize the term 'dude' in pop culture.

From there, Penn steadily built an impressive body of work as an actor while gradually moving into directing as well. His performances earned him Academic Awards nominations for Dead Man Walking, which premiered in 1995, Sweet and Lowdown in 1999, and I am Sam in 2001. The big win finally came for his role in Mystic River, a Boston crime drama produced in 2003. Then, in 2008, Sean Penn claimed his second award for producing Milk, a film that told the story of real-life gay rights icon Harvey Milk.

Beyond his remarkable achievements on screen, Penn has never shied away from speaking out on social and political issues. His dedication to free speech was formally honored in December 2006, when he received the Christopher Reeve First Amendment Award.