Gifted and versatile Sean Penn (1960) is an American actor and director. Penn is a powerhouse film performer capable of intensely moving work, who has gone from strength to strength during a colourful film career. He won an Oscar in 2004 for his leading role in Mystic River, after having been nominated three times before. In 2009, he won another Oscar for Milk. Penn is also the recipient of more than 45 other film awards, including a Silver Bear for Dead Man Walking (1995). Penn has also drawn much media attention for his stormy private life and political viewpoints.
![Sean Penn]()
French postcard by La Cinémathèque française. Photo: Dennis Hopper. Caption: Sean Penn, 1988.
![Madonna and Sean Penn in Shanghai Surprise (1986)]()
French postcard by Editions Humour à la Carte, Paris, no. A-C 1215. Photo: UGC Distribution. Madonna and Sean Penn in Shanghai Surprise (Jim Goddard, 1986).
Sean Justin Penn was born in Santa Monica, in 1960. Penn is the son of director Leo Penn, who was blacklisted during McCarthy's reign for refusing to testify, and actress Eileen Ryan (née Annucci). He has two brothers: actor Chris Penn (1965-2006) and musician Michael Penn.
He grew up in Santa Monica, in a neighborhood populated by future celebrities Charlie Sheen and Emilio Estevez, the sons of actor Martin Sheen. The children spent much of their free time together, making a number of amateur films shot with Super-8 cameras. Still, Penn's original intention was to attend law school, although he ultimately skipped college to join the Los Angeles Repertory Theater.
After making his professional debut on an episode of television's Barnaby Jones (1979), he relocated to New York, where he soon appeared in the play 'Heartland'. A TV movie, The Killing of Randy Webster (Sam Wanamaker, 1981), followed before he made his feature debut later that same year as the military cadet defending his academy against closure in Taps (Harold Becker, 1981).
He then had his breakthrough as fast-talking surfer stoner Jeff Spicoli in Fast Times at Ridgemont High (Amy Heckerling, 1982). Jason Ankeny at AllMovie: "He stole every scene in which he appeared, helping to elevate the picture into a classic of the teen comedy genre; however, the quirkiness which would define his career quickly surfaced as he turned down any number of Spicoli-like roles to star in the 1983 drama Bad Boys, followed a year later by the Louis Malle caper comedy Crackers and the period romance Racing With the Moon. While none of the pictures performed well at the box office, critics consistently praised Penn's depth as an actor."
He next contributed a stellar performance as a drug addict turned government spy alongside Timothy Hutton in the Cold War spy thriller The Falcon and the Snowman (John Schlesinger, 1985), followed by a teaming with icy Christopher Walken in the chilling At Close Range (James Foley, 1986). Penn's brother Chris played his brother in the film and their mother played the role of their grandmother.
The youthful Sean then paired up with his then-wife, pop diva Madonna in the woeful, and painful, Shanghai Surprise (Jim Goddard, 1986), which was savaged by the critics, but Sean bounced back with a great job as a hot-headed young cop in Colors (Dennis Hopper, 1988), gave another searing performance as a US soldier in Vietnam committing atrocities in Casualties of War (Brian De Palma, 1989) and appeared alongside Robert De Niro in the uneven comedy We're No Angels (Neil Jordan, 1989).
![Sean Penn in At Close Range (1986)]()
Dutch collectors card. Photo: Sean Penn in At Close Range (James Foley, 1986).
![Madonna and Sean Penn in Shanghai Surprise (1986)]()
French postcard by Editions Humour à la Carte, Paris, no. A-C 1217. Photo: UGC Distribution. Madonna and Sean Penn in Shanghai Surprise (Jim Goddard, 1986).
During the 1990s, Sean Penn really got noticed by critics as a mature, versatile, and accomplished actor, with a string of dynamic performances in first-class films. Almost unrecognisable with frizzy hair and thin-rimmed glasses, Penn was simply brilliant as corrupt lawyer David Kleinfeld in the gangster movie Carlito's Way (Brian De Palma, 1993) and he was still in trouble with authority as a Death Row inmate pleading with a caring nun (Susan Sarandon) to save his life in Dead Man Walking (Tim Robbins, 1995), for which he received his first Oscar nomination.
Penn had also moved into directing, with the quirky but interesting The Indian Runner (1991), about two brothers with vastly opposing views on life, and in 1995 he directed Jack Nicholson in The Crossing Guard (1995). Both films received overall positive reviews from critics.
Sean then played the brother of wealthy Michael Douglas, involving him in a mind-snapping scheme in The Game (David Fincher, 1997), and also landed the lead role of Sgt. Eddie Walsh in the star-studded anti-war film The Thin Red Line (Terrence Malick, 1998), before finishing the 1990s playing an offbeat 1930s jazz guitarist in Sweet and Lowdown (Woody Allen, 1999). For this part, he scored another Oscar nomination.
Sean Penn played a mentally disabled father fighting for custody of his seven-year-old daughter in I Am Sam (Jessie Nelson, 2001). He received his third Oscar nomination for this role, but in the following years, he finally won the Oscar for the best male lead of the year. He won the first for his part as an anguished father seeking revenge for his daughter's murder in the gut-wrenching Mystic River (Clint Eastwood, 2003), and the second six years later for his role as the gay politician and civil rights activist Harvey Milk in Milk (Gus Van Sant, 2008).
Jason Ankeny at AllMovie: "The Oscar (for Mystic River), coupled with a standing ovation by the audience, showed once and for all that Penn's unorthodox approach to his acting career hadn't had an adverse effect on his popularity"
In between, he played a mortally ill college professor in 21 Grams (Alejandro G. Iñárritu, 2003) and a possessed businessman in The Assassination of Richard Nixon (Niels Mueller, 2004) with Naomi Watts. Penn was a militant opponent of the Iraq war. He also supports Sea Shepherd and is on the advisory board of this organisation. Singer Eddie Vedder of Pearl Jam, who is friends with Penn, wrote soundtracks for several films in which Penn acted or which were directed by him, including Dead Man Walking (Tim Robbins, 1995), I Am Sam (Jessie Nelson, 2001), and Into the Wild (Sean Penn, 2007).
Sean Penn also appeared in The Tree of Life (Terrence Malick, 2011) with Brad Pitt, and The Professor and the Madman (Farhad Safinia, 2019) opposite Mel Gibson. In March 2018, he published the novel 'Bob Honey Who Just Do Stuff'.
Penn was engaged to actress Elizabeth McGovern, who played him in Racing with the Moon (Richard Benjamin, 1984). He married singer Madonna in 1985 and divorced her in 1989. He then began a relationship with actress Robin Wright, with whom he had a daughter Dylan in 1991 and a son Hopper in 1993, and married in 1996. A divorce petition followed in December 2007, and became final in 2009, since then Penn has had relationships with actresses Scarlett Johansson and Charlize Theron, among others. In 2016, he began a relationship with Australian actress Leila George, whom he married in July 2020. She filed for divorce in late 2021.
![Madonna and Sean Penn in Shanghai Surprise (1986)]()
French postcard by Editions Humour à la Carte, Paris, no. A-C 1218. Photo: UGC Distribution. Madonna and Sean Penn in Shanghai Surprise (Jim Goddard, 1986).
![Sean Penn]()
French postcard, no. AB 2104. Caption: Sean Penn beard.
Sources: Jason Ankeny (AllMovie), Wikipedia (Dutch), and IMDb.
French postcard by La Cinémathèque française. Photo: Dennis Hopper. Caption: Sean Penn, 1988.
French postcard by Editions Humour à la Carte, Paris, no. A-C 1215. Photo: UGC Distribution. Madonna and Sean Penn in Shanghai Surprise (Jim Goddard, 1986).
He stole every scene in which he appeared
Sean Justin Penn was born in Santa Monica, in 1960. Penn is the son of director Leo Penn, who was blacklisted during McCarthy's reign for refusing to testify, and actress Eileen Ryan (née Annucci). He has two brothers: actor Chris Penn (1965-2006) and musician Michael Penn.
He grew up in Santa Monica, in a neighborhood populated by future celebrities Charlie Sheen and Emilio Estevez, the sons of actor Martin Sheen. The children spent much of their free time together, making a number of amateur films shot with Super-8 cameras. Still, Penn's original intention was to attend law school, although he ultimately skipped college to join the Los Angeles Repertory Theater.
After making his professional debut on an episode of television's Barnaby Jones (1979), he relocated to New York, where he soon appeared in the play 'Heartland'. A TV movie, The Killing of Randy Webster (Sam Wanamaker, 1981), followed before he made his feature debut later that same year as the military cadet defending his academy against closure in Taps (Harold Becker, 1981).
He then had his breakthrough as fast-talking surfer stoner Jeff Spicoli in Fast Times at Ridgemont High (Amy Heckerling, 1982). Jason Ankeny at AllMovie: "He stole every scene in which he appeared, helping to elevate the picture into a classic of the teen comedy genre; however, the quirkiness which would define his career quickly surfaced as he turned down any number of Spicoli-like roles to star in the 1983 drama Bad Boys, followed a year later by the Louis Malle caper comedy Crackers and the period romance Racing With the Moon. While none of the pictures performed well at the box office, critics consistently praised Penn's depth as an actor."
He next contributed a stellar performance as a drug addict turned government spy alongside Timothy Hutton in the Cold War spy thriller The Falcon and the Snowman (John Schlesinger, 1985), followed by a teaming with icy Christopher Walken in the chilling At Close Range (James Foley, 1986). Penn's brother Chris played his brother in the film and their mother played the role of their grandmother.
The youthful Sean then paired up with his then-wife, pop diva Madonna in the woeful, and painful, Shanghai Surprise (Jim Goddard, 1986), which was savaged by the critics, but Sean bounced back with a great job as a hot-headed young cop in Colors (Dennis Hopper, 1988), gave another searing performance as a US soldier in Vietnam committing atrocities in Casualties of War (Brian De Palma, 1989) and appeared alongside Robert De Niro in the uneven comedy We're No Angels (Neil Jordan, 1989).
Dutch collectors card. Photo: Sean Penn in At Close Range (James Foley, 1986).
French postcard by Editions Humour à la Carte, Paris, no. A-C 1217. Photo: UGC Distribution. Madonna and Sean Penn in Shanghai Surprise (Jim Goddard, 1986).
An unorthodox approach to his acting career
During the 1990s, Sean Penn really got noticed by critics as a mature, versatile, and accomplished actor, with a string of dynamic performances in first-class films. Almost unrecognisable with frizzy hair and thin-rimmed glasses, Penn was simply brilliant as corrupt lawyer David Kleinfeld in the gangster movie Carlito's Way (Brian De Palma, 1993) and he was still in trouble with authority as a Death Row inmate pleading with a caring nun (Susan Sarandon) to save his life in Dead Man Walking (Tim Robbins, 1995), for which he received his first Oscar nomination.
Penn had also moved into directing, with the quirky but interesting The Indian Runner (1991), about two brothers with vastly opposing views on life, and in 1995 he directed Jack Nicholson in The Crossing Guard (1995). Both films received overall positive reviews from critics.
Sean then played the brother of wealthy Michael Douglas, involving him in a mind-snapping scheme in The Game (David Fincher, 1997), and also landed the lead role of Sgt. Eddie Walsh in the star-studded anti-war film The Thin Red Line (Terrence Malick, 1998), before finishing the 1990s playing an offbeat 1930s jazz guitarist in Sweet and Lowdown (Woody Allen, 1999). For this part, he scored another Oscar nomination.
Sean Penn played a mentally disabled father fighting for custody of his seven-year-old daughter in I Am Sam (Jessie Nelson, 2001). He received his third Oscar nomination for this role, but in the following years, he finally won the Oscar for the best male lead of the year. He won the first for his part as an anguished father seeking revenge for his daughter's murder in the gut-wrenching Mystic River (Clint Eastwood, 2003), and the second six years later for his role as the gay politician and civil rights activist Harvey Milk in Milk (Gus Van Sant, 2008).
Jason Ankeny at AllMovie: "The Oscar (for Mystic River), coupled with a standing ovation by the audience, showed once and for all that Penn's unorthodox approach to his acting career hadn't had an adverse effect on his popularity"
In between, he played a mortally ill college professor in 21 Grams (Alejandro G. Iñárritu, 2003) and a possessed businessman in The Assassination of Richard Nixon (Niels Mueller, 2004) with Naomi Watts. Penn was a militant opponent of the Iraq war. He also supports Sea Shepherd and is on the advisory board of this organisation. Singer Eddie Vedder of Pearl Jam, who is friends with Penn, wrote soundtracks for several films in which Penn acted or which were directed by him, including Dead Man Walking (Tim Robbins, 1995), I Am Sam (Jessie Nelson, 2001), and Into the Wild (Sean Penn, 2007).
Sean Penn also appeared in The Tree of Life (Terrence Malick, 2011) with Brad Pitt, and The Professor and the Madman (Farhad Safinia, 2019) opposite Mel Gibson. In March 2018, he published the novel 'Bob Honey Who Just Do Stuff'.
Penn was engaged to actress Elizabeth McGovern, who played him in Racing with the Moon (Richard Benjamin, 1984). He married singer Madonna in 1985 and divorced her in 1989. He then began a relationship with actress Robin Wright, with whom he had a daughter Dylan in 1991 and a son Hopper in 1993, and married in 1996. A divorce petition followed in December 2007, and became final in 2009, since then Penn has had relationships with actresses Scarlett Johansson and Charlize Theron, among others. In 2016, he began a relationship with Australian actress Leila George, whom he married in July 2020. She filed for divorce in late 2021.
French postcard by Editions Humour à la Carte, Paris, no. A-C 1218. Photo: UGC Distribution. Madonna and Sean Penn in Shanghai Surprise (Jim Goddard, 1986).
French postcard, no. AB 2104. Caption: Sean Penn beard.
Sources: Jason Ankeny (AllMovie), Wikipedia (Dutch), and IMDb.