The exposure soon won Penn the role of a military cadet opposite Timothy Hutton in Harold Becker’s Taps. His next role was in flamboyant contrast: Jeff Spicoli, the cheery pothead surfer in Amy Heckerling’s Fast Times at Ridgemont High, a role that made Penn a bonafide movie star.

Penn followed his breakout role in Fast Times with several diverse roles that showcased his depth and range including Bad Boys, Louis Malle’s Crackers, Richard Benjamin’s Racing with the Moon and John Schlesinger’s The Falcon and the Snowman, where he received strong critical recognition re-teaming with Taps co-star Timothy Hutton. He followed with James Foley’s At Close Range, opposite Christopher Walken and his brother, Christopher Penn.

Penn starred in “Hurlyburly,” the Los Angeles production written and directed by David Rabe.  In addition, he directed a one-act play, “The Kindness of Women” at the Pink Theater in Santa Monica. In yet another juxtaposition of high contrast roles, Penn co-starred with Robert DeNiro in We’re No Angels and with Gary Oldman in State of Grace, directed by Phil Joanau.  It was on State of Grace where Penn met his wife actress Robin Wright-Penn.

Sean Penn made his screenwriting and directorial debut with the Mount Film Group production of The Indian Runner.  For Penn, a long-time secret writer, The Indian Runner is both autobiographical and a personal vision.

In 1993, Penn returned to acting starring opposite Al Pacino in Brian De Palma’s Carlito’s Way.  His performance in that film garnered further critical acclaim including a Golden Globe Award for Best Supporting Actor.

The Crossing Guard, which starred Jack Nicholson, David Morse, Anjelica Huston and Robin Wright-Penn marked the second project which Penn wrote, directed and produced. 

  In Dead Man Walking Penn plays a convicted murderer awaiting execution who learns to trust and care for the nun who becomes his spiritual advisor. Critics worldwide championed this to be Penn’s finest work; he won Academy Award and Golden Globe nominations for Best Actor.

In the fall of 1997, Penn starred in three films including Nick Cassavetes’ She’s So Lovely (which he also produced) opposite Robin Wright-Penn and John Travolta, David Fincher’s The Game opposite Michael Douglas and Oliver Stone’s U-Turn opposite Nick Nolte.  Penn received the Best Actor Award at the 1997 Cannes Film Festival for She’s So Lovely.

In late 1998 Penn received critical acclaim for his performances in Terrence Malick’s The Thin Red Line and Anthony Drazen’s Hurlyburly, for which he won the Best Actor Award at the Venice Film Festival.

In 1999 Penn starred in Woody Allen’s Sweet and Lowdown, for which he received a Golden Globe and Academy Award Best Actor nomination.  The actor followed this performance with Up At the Villa, directed by Philip Haas, and along with Woody Harrelson starred in Sam Shepard’s new play, “The Late Henry Moss” at the Theater on the Square in San Francisco. 

Recently Penn was behind the camera, helming and producing the critically acclaimed film The Pledge, which stars Jack Nicholson, Vanessa Redgrave and Robin Wright-Penn. He will next be seen in the indie feature Weight of Water.