- 2009: Nominated for the 2008 Academy Award for Best Performance by an Actor in a Leading Role (“Milk”)
- 2008: Portrayed San Francisco city supervisor and gay rights activist, Harvey Milk in the Gus Van Sant directed "Milk"
- 2008: Nominated for the 2008 Golden Globe Award for Best Performance by an Actor in a Motion Picture – Drama (“Milk”)
- 2008: Nominated for the 2008 Screen Actors Guild Award for Outstanding Performance by a Male Actor in a Leading Role (“Milk”)
- 2008: Nominated for the 2008 Independent Spirit Award for Best Male Lead (“Milk”)
- 2007: Directed "Into the Wild," a drama based on the 1996 non-fiction book of the same name by Jon Krakauer about the life and death of Christopher McCandless; also adapted the screenplay; earned a DGA nomination for Outstanding Directorial Achievement in Feature Film
- 2006: Played corrupt politician Willie Stark in the big-screen adaptation of the Robert Penn Warren novel, "All the King's Men"
- 2005: Starred opposite Nicole Kidman in Sydney Pollack's "The Interpreter"
- 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 "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: Had a recurring guest role on the NBC sitcom "Friends"
- 2001: Narrated the documentary "Dogtown and Z-Boys"; screened at Sundance (released theatrically in US in 2002)
- 2001: Starred as a mentally challenged man fighting for custody of his daughter in "I Am Sam"; earned third Best Actor Oscar nomination
- 2001: Directed the feature film "The Pledge" starring Jack Nicholson
- 2000: Acted in Kathryn Bigelow's "The Weight of Water"
- 2000: Made a cameo appearance as a Cuban peasant in Julian Schnabel's "Before Night Falls"
- 2000: Returned to stage acting opposite Nick Nolte in Sam Shepard's play "The Late Henry Moss"
- 1999: Cast as the world's second best guitar player in Woody Allen's "Sweet and Lowdown"; received second Best Actor Academy Award nomination
- 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 the Los Angeles stage production of "Remembrance" starring his parents
- 1997: Co-starred with Robin Wright Penn in "She's So Lovely"; directed by Nick Cassavetes from a script by the late John Casavetes
- 1995: Portrayed a killer on death row in "Dead Man Walking"; received first Best Actor Academy Award nomination
- 1995: Producing debut, "The Crossing Guard"; starred Jack Nicholson and Anjelica Huston; Penn also wrote and directed
- 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 the Los Angeles stage production of David Rabe's "Hurlyburly"
- 1988: Starred opposite Robert Duvall as L.A. street cops in "Colors"; film directed by Dennis Hopper
- 1988: Directed by father Leo in "Judgment in Berlin" (shown on TV as "Escape to Freedom")
- 1986: Acted with brother Christopher in "At Close Range"; mother Eileen Ryan played their grandmother
- 1986: Starred opposite then-wife Madonna in the misfire, "Shanghai Surprise"
- 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"
- 1983: Earned favorable reviews as a troubled youth in "Bad Boys"
- 1982: Breakthrough feature role, playing stoner Jeff Spicoli in "Fast Times at Ridgemont High"
- 1981: Film acting debut in "Taps"; played a rebellious cadet at a military school
- 1981: Made Broadway debut in "Heartland" (show closed after two months)
- 1981: Had a supporting role in the CBS movie, "The Killing of Randy Webster"
- 1979: Made professional acting debut in the CBS series "Barnaby Jones"
- 1970: Family settled in Malibu, CA and he became friendly with Emilio Estevez, Charlie Sheen and Rob Lowe
- Apprenticed for two years with the Group Repertory Theatre in Los Angeles
- Raised in the San Fernando Valley, CA
- Formed Clyde Is Hungry Productions
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