Sean Penn first came into Hollywood’s radar with his performance in the 1981 movie Taps. He followed this up with the role that would follow him the rest of his career when he played the goofy stoner Jeff Spicoli in the 1982 movie Fast Times At Ridgemont High. Fast Times went on to become a hit comedy and Penn started to get looked at as a potential stereotypical stoner actor but his performance in both movies showed Hollywood producers a potential star and the roles he started to get would help him leave Jeff Spicoli way behind.
In 1985 Sean Penn appeared in the hit movie The Falcon And The Snowman and was given a chance to show his real acting ability. People could not believe that this was the same person that just played Jeff Spicoli a few years earlier and his performance was critically hailed. But his personal life was overshadowing his professional life as his marriage to pop diva Madonna, and his continuous run ins with the law for punching people in the face, was starting to grab more headlines than his movie roles. In 1989 he divorced Madonna and set himself up to make a huge impact in the 1990’s.
In 1993 he had a excellent performance in the hit movie Carlito’s Way and in 1995 he received his first Oscar nomination for his work in the movie Dead Man Walking. In 1998 he once again wowed the critics with his performance in The Thin Red Line and for his work in the 1999 movie Sweet And Lowdown he was once again nominated for an Oscar. In 2001 he played a mentally challenged father trying to win his daughter’s custody in the court system and again he was nominated for an Oscar for his performance. Finally Sean Penn won the Oscar for best leading actor with his performance in the 2003 Clint Eastwood movie Mystic River. Did I mention that he is also a director, writer, and producer?