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Actor, writer, director, producer. Born August 17, 1960, in
Burbank, California. Penn grew up in Los Angeles and attended
Santa Monica High School, along with fellow students and future
actors Emilio Estevez, Charlie Sheen, and Rob Lowe. An early
interest in filmmaking, specifically directing, led to a passion
for acting, and Penn moved to New York City when he was 19 to
pursue a career as an actor. He soon landed a part in a Broadway
play, Heartland. In 1981, he made his film debut, in the
military school drama Taps, alongside star Timothy Hutton
(already an Oscar-winner for 1980’s Ordinary People) and fellow
up-and-comer Tom Cruise.
Penn’s breakthrough role came a year later, when he played
perpetually stoned surfer Jeff Spicoli in the high school comedy
Fast Times at Ridgemont High. He garnered acclaim for his first
starring role, in 1983’s Bad Boys and for The Falcon and the
Snowman (1985), also starring Hutton. In 1985, Penn gained a
whole new measure of fame when he married pop goddess Madonna.
Their tumultuous four year marriage produced one dismal movie,
1986’s Shanghai Surprise, and a barrage of tabloid headlines.
Penn’s “bad boy” image only increased with his continued
hostility towards the aggressive paparazzi—he served 34 days in
prison in 1987 for punching an extra who had tried to take his
picture on the set of the film Colors, co-starring Robert Duvall
and directed by Dennis Hopper. Penn and Madonna divorced in
1989.
In 1991, two years after earning rave reviews for his
performance in Casualties of War (1989), directed by Brian De
Palma and co-starring Michael J.
Fox, Penn directed his first film, the little seen feature The
Indian Runner. Though he had claimed he was quitting acting,
Penn was back in front of the camera in 1993, playing a
coke-addled criminal lawyer in De Palma’s Carlito’s Way,
co-starring Al Pacino. In 1995, he starred as a death row inmate
searching for salvation in the critical and popular success Dead
Man Walking, directed by Tim Robbins and co-starring Susan
Sarandon. Penn’s powerful performance earned him his first
Academy Award nomination, for Best Actor. That same year, he
wrote, produced, and directed The Crossing Guard, a dark drama
starring his boyhood idol, Jack Nicholson.
Penn’s edgy good looks and undeniable talent might have secured
him a place among Hollywood’s A-list leading men; instead, he
has largely neglected headline roles in big-budget films in
favor of decidedly unheroic roles in darker, more understated
films, with varying degrees of success. He starred as a
lovesick, jealous husband in Nick Cassavetes's She’s So Lovely
(1997), co-starring John Travolta and Penn’s real-life (second)
wife, Robin Wright Penn (whom he fell in love with while filming
State of Grace in 1990 and married in 1996 after a turbulent
five-year romance). Although Penn (who also served as executive
producer) won the Best Actor Award at the Cannes Film Festival,
She's So Lovely did not attract a wide audience. Penn appeared
in two other major films in 1997: the poorly received U-Turn,
directed by Oliver Stone and co-starring Nick Nolte and Jennifer
Lopez, and the hit action-thriller The Game, starring Michael
Douglas.
In Hurlyburly (1998), Penn reprised a role he had played on the
Los Angeles stage in 1988, co-starring with Kevin Spacey as a
brutal, misogynistic Hollywood agent. In 1998, Penn also starred
in the critically acclaimed World War II drama, The Thin Red
Line, directed by Terrence Malick.
In 1999, the unpredictable Penn took Hollywood by surprise when
he garnered a second Academy Award nomination for Best Actor,
turning in another searing, darkly complex performance as the
dissolute jazz guitarist at the center of Woody Allen's Sweet
and Lowdown, alongside fellow Oscar-nominee Samantha Morton. In
2000, he starred in the romantic Up in the Villa, with Kristen
Scott Thomas, and The Weight of Water. His third directorial
feature, the thriller The Pledge, starred Nicholson and Robin
Wright Penn. In 2002, Penn starred opposite Michelle Pfeiffer in
I Am Sam, playing a mentally disabled man who fights to regain
custody of his young daughter. The following year, he starred in
Clint Eastwood's small town drama Mystic River, for which he
earned an Academy Award for Best Actor.
Penn and Robin Wright Penn live in Marin County, California,
with their daughter, Dylan, and son, Hopper. Wright Penn, best
known for her roles in The Princess Bride (1987), Forrest Gump
(1993), and Message in a Bottle (1999), also appeared in
Hurlyburly and The Crossing Guard. Penn’s mother, Eileen Ryan,
is an actress who appeared in Magnolia, released in late 1999.
His father, Leo Penn, who died in 1998, was an
actor-turned-director who was blacklisted during the 1940s and
1950s when he refused to name names of Communist sympathizers in
Hollywood. Penn has two brothers: Christopher, an actor who
appeared with his brother in At Close Range (1986), and Michael,
a rock musician.
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