Born August 17, 1960 in Santa Monica, California, the second son of actor-director Leo Penn and actress Eileen Ryan, Sean Penn is the fourth actor to receive three Oscars and the first since Walter Brennan to win all three on successive nominations.

The actor’s older brother is composer Michael Penn (born 1958).  His younger brother was actor Chris Penn (1965-2006).

Penn made his acting debut as an extra on a 1974 episode of Little House on the Prairie directed by his father.  He did not make his film debut until 1981’s Taps in which he played a military cadet.  His next film, 1982’s Fast Times at Ridgemont High, made him a star.  1984’s Racing with the Moon and 1985’s The Falcon and the Snowman brought him critical acclaim.  That same year he met and married pop icon Madonna with whom he had a rocky relationship until their 1989 divorce.

Despite being a tabloid bad boy during his marriage to Madonna, Penn received acclaim for his on-screen performances in 1985’s At Close Range, 1986’s Colors, and 1989’s Casualties of War.

The actor then began a relationship with actress Robin Wright in 1989 that resulted in the births of their children, future actress Dylan Penn in 1991 and future actor Hopper Penn in 1992.  During this period, he continued to receive strong notices for his performances in 1990’s State of Grace and 1993’s Carlito’s Way as well as for his direction of 1991’s The Indian Runner.

In 1995 Penn directed Jack Nicholson and Anjelica Huston in The Crossing Guard and starred opposite Susan Sarandon in Dead Man Walking directed by Sarandon’s longtime partner, fellow actor Tim Robbins.  Penn was nominated for an Oscar for his portrayal of a prisoner on death row while Sarandon won an Oscar for playing the nun he comforts him.  He and Wright married in 1996 and were divorced in 2010.

Penn won the prestigious Best Actor award at the 1997 Cannes Film Festival for She’s So Lovely opposite Wright.  That same year he had a major success in The Game opposite Michael Douglas.  Other hits followed including 1999’s Sweet and Lowdown and 2001’s I Am Sam. Both of which earned him Oscar nominations.  In 2003, he received awards recognition for both Mystic River and 21 Grams, earning his fourth Oscar nomination and first win for the former.  His Dead Man Walking director also won for his supporting role in the film which was directed by Clint Eastwood.

In 2007 Penn was in Oscar speculation for his direction of Into the Wild but failed to make the cut.  Returning to acting the following year, he not only made the cut but won his second Oscar for Milk.

Since winning his second Oscar, Penn has been in the news for his many social causes including founding the J/P Haitian Relief Organization following the devastating 2010 Haitian earthquake. He married third wife Leila George in 2020.  They divorced in 2022.

Penn visited Ukraine for the first time in 2022 at the start the Russia-Ukraine War and returned several times, most recently on March 15, 2026 the day he won his third Oscar for his supporting role in 2025’s One Battle After Another, his best role in years.  Few have ever had a better excuse for missing a big Oscar win.

Sean Penn is busier than ever at 65.

ESSENTIAL FILMS

DEAD MAN WALKING (1995), directed by Tim Robbins

Based on Sister Helen Prejean’s book of the same name, Penn received his first Oscar nomination for playing the title role, that of a convict on death row who is comforted by Sister Helen who empathizes with both killer and victims.  She’s played by Susan Sarandon who won her only Oscar on her fifth nomination for her performance.  Also nominat4ed were Tim Robbins for his direction and Bruce Springsteen for the film’s title song.  Robbins, who also wrote the film’s screenplay, would go on to win an Oscar for supporting Penn in Mystic River for which Penn also won.  Springsteen won an Oscar two years earlier for “Streets of Philadelphia” from Philadelphia.

MYSTIC RIVER (2003), directed by Clint Eastwood

Nominated for 6 Oscars including Best Picture, Director, Adapted Screenplay by Brian Helgeland, Actor (Penn), Supporting Actor (Tim Robbins), and Supporting Actress (Marcia Gay Harden), with both Penn and Robbins winning.  Penn, Robbins, and Kevin Bacon are lifelong friends.  The tale revolves around a traumatic childhood incident and in the present time the murder of Penn’s 19-year-old daughter being investigated by detective Bacon.  Harden plays Robbins’ wife.  Laura Linney plays Penn’s second wife and Laurence Fishburne plays Bacon’s detective partner.  The film’s ending left audiences gasping.

INTO THE WILD (2007), directed by Sean Penn

Nominated for 7 Critics Choice awards including Best Picture, Director, Adapted Screenplay (by Penn), Actor (Emile Hirsch), Supporting Actor (Hal Halbrook), Supporting Actress (Catherine Keener), and song “Guaranteed” by Eddie Vedder, this true story about a recent Emory University graduate, a top student and athlete Christopher McCandless abandons his possessions, gives his entire $24,000 savings account to charity and hitchhikes to Alaska to live in the wilderness, was unfairly whittled down to just two Oscar nominations for Holbrook and the film’s editing.  Penn also served as a producer on the film, his fourth as a director.

MILK (2008), directed by Gus Van Sant

Nominated for 8 Oscars including Best Picture, Director, Original Screenplay (Dustin Lance Black), Actor (Penn), Supporting Actor (Josh Brolin), Film Editing, Costume Design, and Score, this story of American gay activist Harvey Milk, who fought for gay rights and was elected as California’s first openly gay official, won for Penn’s portrayal of Milk and Black’s screenplay.  Brolin played Milk’s assassin.  The film also featured strong support from Emile Hirsch, James Franco, Diego Luna, Allison Pill, and Victor Garber as San Francisco Mayor Moscone who was assassinated along with Milk in 1978.

ONE BATTLE AFTER ANOTHER (2025), directed by Paul Thomas Anderson

Anderson’s anti-Fascist action film received 13 Oscar nominations for Best Picture, Director, Adapted Screenplay (written by Anderson), Actor (Leonardo DiCaprio), Supporting Actor (Penn and Benicio Del Toro), Supporting Actress (Teyana Taylor), Casting, Cinematography, Film Editing, Production Design, Score, and Sound.  It won six including Picture, Director, Adapted Screenplay, Casting, Film Editing, and Supporting Actor for no-show Penn who was making one of his frequent trips to war-torn Ukraine.  Penn was given a special Oscar by Ukraine made from metal from the country’s railroad tracks destroyed by Russia during the ongoing war.

SEAN PENN AND OSCAR

Dead Man Walking (1995) – nominated – Best Actor

Sweet and Lowdown (1999) – nominated – Best Actor

I Am Sam (2001) – nominated – Best Actor

Mystic River (2003) – Oscar– Best Actor

Milk (2008) – Oscar – Best Actor

One Battle After Another (2008) – Oscar – Best Actor