Raised in the San Fernando Valley, California

Family settled in Malibu, California; was friendly with the neighbor children, Emilio Estevez, Charlie Sheen and Rob Lowe

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

Made professional acting debut as guest star on TV's "Barnaby Jones"

Drove cross-country to NYC

Made Broadway debut in "Heartland" (previews began in January; show closed in March)

Had a supporting role in CBS movie, "The Killing of Randy Webster"

Film acting debut in "Taps"; played a rebellious cadet at a military school

Breakthrough feature role, Jeff Spicoli in "Fast Times at Ridgemont High"

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

First feature as star, "Bad Boys"

Delivered standout performance as a desperate, amoral, drugged-out kid in "The Falcon and the Snowman"

Starred opposite then-wife Madonna in misfire, "Shanghai Surprise"

Acted with brother Christopher in "At Close Range"; mother Eileen Ryan played their grandmother

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"

Starred opposite Robert Duvall as L.A. street cops in "Colors", directed by Dennis Hopper

Directed by father Leo in "Judgment in Berlin", shown on TV as "Escape to Freedom"

Acted in Los Angeles stage production of David Rabe's "Hurlyburly"

First film with director Brian De Palma, "Casualties of War", scripted by Rabe

First film with future wife Robin Wright, "State of Grace"

Film directing and writing debut, "Indian Runner"; claimed to have retired from acting

Returned to the screen in a supporting role in De Palma's "Carlito's Way"

Formed Clyde Is Hungry Productions

Received first Best Actor Oscar nomination for his portrayal of a killer on death row in "Dead Man Walking"

Producing debut, "The Crossing Guard", starring Jack Nicholson and Anjelica Huston; also wrote and directed; mother, father and Wright were all in cast

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"

Executive produced (in association with the Helicon Theatre Company) a Los Angeles stage production of Irish playwright Graham Reid's "Remembrance", starring his parents

Made a member of the Actors Studio to honor the passing of his father, an Actors Studio teacher

Reprised his stage role of Eddie for the screen version of "Hurlyburly"; fifth film with wife

Acted in Terrence Malick's return to directing after an absence of 20 years, "The Thin Red Line"

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

Made uncredited cameo appearance in "Being John Malkovich"

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

Acted in Kathryn Bigelow's "The Weight of Water"; screened at film festivals; released theatrically in USA in 2002

Made cameo appearance as a Cuban peasant in "Before Night Falls", directed by Julian Schnabel

Returned to stage acting opposite Nick Nolte in Sam Shepard's play "The Late Henry Moss"; performed in San Francisco

Narrated the documentary "Dogtown and Z-Boys"; screened at Sundance; released theatrically in USA in 2002

Directed the feature film "The Pledge", starring Jack Nicholson

Made several appearances in a recurring guest role on the NBC sitcom "Friends"

Starred as a mentally challenged man fighting for custody of his daughter in the feature "I Am Sam"; earned third Best Actor Oscar nomination

Had small role in the romance "It's All About Love"

Starred in the emotional drama feature "Mystic River", directed by Clint Eastwood; received a SAG nomination for Best Actor

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

Starred opposite Nicole Kidman in "The Interpreter" directed by Sydney Pollack

Played corrupt politician Willie Stark in the big-screen adaptation of the Robert Penn Warren novel "All the King's Men"

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