Sean Penn movies have changed drastically over the years. The progression of this actor’s career has been amazing. While he started out as a young slacker in Richard Linklater movies, he has since developed into an Academy Award-winning actor in prestigious movies. The fact that the man once known as Spicoli has become one of Hollywood’s heavy hitters make him a man worth looking into.

“Fast Times at Ridgemont High” When “Fast Times at Ridgemont High” came out in 1982, the star of the movie was supposed to be Judge Reinhold. However, a slacker who cared more about surfing than studying stole the movie from everyone involved. Sean Penn movies begin and end, for some fans, with this movie tracing the life of a group on high school friends. Penn starred as Jeff Spicoli, a kid who ordered pizza delivered to his history class and always butted hands with the strict teacher Mr. Hand.

“Carlito’s Way” Eleven years after playing a high school slacker, Sean Penn teamed him with Al Pacino in one of the greatest gangster movies of all time. Based on the novel “After Hours,” Pacino plays Carlito, a Puerto Rican criminal who is freed by a technicality found by his attorney, played by Sean Penn. The role earned Penn a Golden Globe nomination for Best Supporting Actor.

“Dead Man Walking” This Sean Penn movie earned the actor his first of five Oscar nominations. Penn plays a prisoner awaiting his execution for the murder of a teenage couple. The movie sees him ask a religious woman to help him earn a pardon and a life sentence instead of death. “Dead Man Walking” was directed by actor Tim Robbins and also starred Robbins’s wife, Susan Sarandon, as Sister Helen. The movie received four Oscar nominations.

“Mystic River” Clint Eastwood adapted this Dennis Lehane novel into an Oscar-nominated drama starring Kevin Bacon, Tim Robbins and Sean Penn. Movies don’t get much better than this as Penn plays a small-town ex-con whose daughter is murdered and he sets out to seek vengeance against the man who did it. Kevin Bacon stars as a childhood friend who now works as a police detective and Tim Robbins is their third friend who was sexually abused as a young boy. The movie is a devastating look at childhood friendship’s corrupted over time and has a gut-wrenching climax.

“Milk” Sean Penn's work in this movie earned the actor another Oscar as he portrayed the true-life political gay rights activist Harvey Milk. The film, directed by Gus Van Sant, follows the life and career of Milk as he became the first openly gay individual elected to California public office. The movie earned a total of eight Oscar nominations, winning two.