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Milestones
- 2005: Starred opposite Nicole Kidman in "The Interpreter" directed by Sydney Pollack
- 2004: Starred opposite Naomi Watts, Don Cheadle and Jack Thompson in "The Assassination of Richard Nixon" based on a true story about a man who tried to hijack a jet and crash it into the White House during Nixon's second term
- 2003: Starred in the emotional drama feature "Mystic River", directed by Clint Eastwood; received a SAG nomination for Best Actor
- 2002: Had small role in the romance "It's All About Love"
- 2001: Narrated the documentary "Dogtown and Z-Boys"; screened at Sundance; released theatrically in USA in 2002
- 2001: Directed the feature film "The Pledge", starring Jack Nicholson
- 2001: Made several appearances in a recurring guest role on the NBC sitcom "Friends"
- 2001: Starred as a mentally challenged man fighting for custody of his daughter in the feature "I Am Sam"; earned third Best Actor Oscar nomination
- 2000: Starred with Kristin Scott Thomas in "Up in the Villa", Phillip Haas' adaptation of the Somerset Maugham novella set in the expatriate community of 1938 Florence
- 2000: Acted in Kathryn Bigelow's "The Weight of Water"; screened at film festivals; released theatrically in USA in 2002
- 2000: Made cameo appearance as a Cuban peasant in "Before Night Falls", directed by Julian Schnabel
- 2000: Returned to stage acting opposite Nick Nolte in Sam Shepard's play "The Late Henry Moss"; performed in San Francisco
- 1999: Had leading role of the world's second best guitar player in Woody Allen's period comedy "Sweet and Lowdown"; received second Academy Award nomination as Best Actor
- 1999: Made uncredited cameo appearance in "Being John Malkovich"
- 1998: Made a member of the Actors Studio to honor the passing of his father, an Actors Studio teacher
- 1998: Reprised his stage role of Eddie for the screen version of "Hurlyburly"; fifth film with wife
- 1998: Acted in Terrence Malick's return to directing after an absence of 20 years, "The Thin Red Line"
- 1997: Executive produced (in association with the Helicon Theatre Company) a Los Angeles stage production of Irish playwright Graham Reid's "Remembrance", starring his parents
- 1997: Co-starred in three major releases: "She's So Lovely" (for which he won the Cannes Best Actor Award), directed by Nick Cassavetes from a script by the late John Casavetes; Penn also served as an executive producer; David Fincher's "The Game"; and Oliver Stone's "U-Turn"
- 1995: Producing debut, "The Crossing Guard", starring Jack Nicholson and Anjelica Huston; also wrote and directed; mother, father and Wright were all in cast
- 1995: Received first Best Actor Oscar nomination for his portrayal of a killer on death row in "Dead Man Walking"
- 1993: Returned to the screen in a supporting role in De Palma's "Carlito's Way"
- 1991: Film directing and writing debut, "Indian Runner"; claimed to have retired from acting
- 1990: First film with future wife Robin Wright, "State of Grace"
- 1989: First film with director Brian De Palma, "Casualties of War", scripted by Rabe
- 1988: Acted in Los Angeles stage production of David Rabe's "Hurlyburly"
- 1988: Directed by father Leo in "Judgment in Berlin", shown on TV as "Escape to Freedom"
- 1988: Starred opposite Robert Duvall as L.A. street cops in "Colors", directed by Dennis Hopper
- 1987: Wound up in L.A. County jail for a month after violating probation in connection with an assault-and-battery charge when he punched an extra on the set of "Colors"
- 1986: Starred opposite then-wife Madonna in misfire, "Shanghai Surprise"
- 1986: Acted with brother Christopher in "At Close Range"; mother Eileen Ryan played their grandmother
- 1985: Delivered standout performance as a desperate, amoral, drugged-out kid in "The Falcon and the Snowman"
- 1983: Returned to Broadway to co-star with Val Kilmer, Jackie Earle Haley and Kevin Bacon in "The Slab Boys"; show closed in April after 48 performances
- 1983: First feature as star, "Bad Boys"
- 1982: Breakthrough feature role, Jeff Spicoli in "Fast Times at Ridgemont High"
- 1981: Made Broadway debut in "Heartland" (previews began in January; show closed in March)
- 1981: Film acting debut in "Taps"; played a rebellious cadet at a military school
- 1981: Had a supporting role in CBS movie, "The Killing of Randy Webster"
- 1980: Drove cross-country to NYC
- 1979: Made professional acting debut as guest star on TV's "Barnaby Jones"
- 1970: Family settled in Malibu, California; was friendly with the neighbor children, Emilio Estevez, Charlie Sheen and Rob Lowe
- Cast as Southern politician Willie Stark in the big-screen adaptation of the Robert Penn Warren novel "All the King's Men" (lensed 2005)
- Raised in the San Fernando Valley, California
- Apprenticed for two years with Group Repertory Theatre, Los Angeles; directed a one-act play, "Terrible Jim Fitch", while there; also worked as an assistant to actor-director Pat Hingle
- Formed Clyde Is Hungry Productions
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