Sean Penn biography, net worth, young, Madonna`s marriage, age, height, awards 2025

Sean Penn Biography

Sean Penn is an actor and director, one of the most compelling and fascinating artists of the '80s and '90s generation. A two-time Oscar winner for his performances in the dramas "Mystic River" and "Milk". Among his landmark films are "Fast Times at Ridgemont High", "Carlito's Way", "Dead Man Walking", "21 Grams", and "I Am Sam".

Sean Penn in a denim shirt against a backdrop of green ivy — Sean Penn

Childhood and Family

Sean Justin Penn was born August 17, 1960, in Santa Monica, California, into a creative family. Both his parents, Leo Penn and Eileen Ryan, were actors. His father had Lithuanian-Jewish roots, while his mother was a Catholic of Irish and Italian descent. They raised their children in a secular household, though.

Sean idolized his father, who instilled in him a sense of pride in serving society and a desire to do something meaningful for the world. Leo Penn served in World War II, then became an actor but landed on the blacklist after being accused of communist sympathies when he refused to testify before the House Un-American Activities Committee. After that, he shifted to directing, eventually working on iconic TV series: "Columbo", "Star Trek", and "Little House on the Prairie".

Collage: Sean Penn as a child with his parents and siblings; Sean Penn's school portrait — Sean Penn as a child with his family

The boy grew up alongside his older brother, Michael, who became a musician, and his younger brother, Chris, who also became an actor (he died in 2006).

Sean grew up in Malibu and attended the local high school, where he shot short films with childhood friends Emilio Estevez and Charlie Sheen. The future star's first screen appearance came in 1974—a small role in an episode of "Little House on the Prairie", which his father was working on.

Young Sean Penn in a plaid shirt next to a boy in a gray cap — Sean Penn in "Little House on the Prairie"

More TV roles followed, including an episode of "Barnaby Jones" in 1979. At 19, Sean Penn moved to New York. The young actor decided to skip college and join the Los Angeles Repertory Theater instead, committing himself fully to his craft.

Career

First Taste of Fame

Strong performances in the Off-Broadway production of "Heartland" and the film "Taps" (both in 1981) put Penn on the map. Taps marked his big-screen debut, with Penn playing a military school cadet in this war drama.

The role that made him famous came a year later – his portrayal of perpetually stoned surfer Jeff Spicoli in the comedy "Fast Times at Ridgemont High" (1982). His character helped popularize the word "dude" in mainstream culture. It's funny how this lightweight role became the launching pad for an actor who'd later become known for incredibly serious and profound dramatic work.

Young Sean Penn with long hair, wearing a blue turtleneck and a blue beanie — Sean Penn in "Fast Times at Ridgemont High"

After that, he showed his range with a series of diverse roles: a troubled teen in the critically acclaimed drama "Bad Boys" (1983).

That same year, he shined on Broadway, starring in John Byrne's play "Slab Boys" alongside Kevin Bacon and Val Kilmer.

In 1985, Penn played Andrew Daulton Lee in "The Falcon and the Snowman", based on the true story of Americans who spied for the Soviet Union.

Marriage to Madonna and Turbulent Years

In 1985, Penn married pop icon Madonna with all the chaos that entailed. They'd met on the set of her "Material Girl" music video. By the time they tied the knot, she'd already released "Like a Virgin" and become a phenomenon.

Wedding photo of Sean Penn and Madonna — Sean Penn and Madonna

Years later, in an interview with Oprah Winfrey, Penn called the marriage "loud" and admitted: "Frankly, I don't remember one conversation in four years of marriage."

This period was rough for the actor's career. The couple starred in the critically panned "Shanghai Surprise" (1986), which bombed spectacularly. Their marriage was constantly plagued by Penn's aggressive confrontations with the press. In December 1987, Madonna filed for divorce but withdrew the petition two weeks later. Still, the split was inevitable, and by January 1989, they'd gone their separate ways.

Comeback and Recognition

Penn bounced back quickly from the divorce. In "Colors" (1988), he delivered a powerful performance as a hot-headed young cop. A year later, he played an American soldier in Vietnam in "Casualties of War".

The '90s finally saw Penn recognized as a mature, multifaceted, and talented actor. With disheveled hair and wire-rimmed glasses, he was brilliant as corrupt lawyer David Kleinfeld in Brian De Palma's gangster film "Carlito's Way" (1993).

Sean Penn with curly hair and round glasses sitting in a chair — Sean Penn in "Carlito's Way"

For his role as a death row inmate in the drama "Dead Man Walking" (1995), he earned his first Oscar nomination. Critic Roger Ebert wrote: "Penn once again proves he's the most powerful actor of his generation."

2000s Triumph

Penn continued to surprise audiences in the new millennium. In the drama "I Am Sam" (2001), he played a single father with an intellectual disability fighting for custody of his seven-year-old daughter (the role earned him another Oscar nomination). In Clint Eastwood's heartbreaking "Mystic River" (2003), he portrayed a grief-stricken father seeking revenge for his daughter's death. This performance won him the Oscar for Best Actor.

An enraged Sean Penn being restrained by five uniformed police officers — Sean Penn in "Mystic River"

In 2003, Penn received the Best Actor prize at the Venice Film Festival for his work in the existential drama "21 Grams".

In November 2008, audiences gave Penn a standing ovation for his portrayal of Harvey Milk in Gus Van Sant's biopic. His performance as the politician and gay rights activist earned him his second Best Actor Oscar.

After that, Penn's involvement in a film became something of a quality stamp: he appeared in "This Must Be the Place" (2011), "Gangster Squad" and "The Secret Life of Walter Mitty" (2013), the action thriller "The Gunman" (2017), the biographical drama "The Professor and the Madman" (2018), and Paul Thomas Anderson's "Licorice Pizza" (2021).

In 2022, Penn teamed up with Julia Roberts for the miniseries "Gaslit", about the Watergate scandal. In 2023, he starred in Christy Hall's directorial debut "Daddio" as a taxi driver, with Dakota Johnson as his co-star.

Sean Penn in a green vest leaning against a yellow taxi cab — Sean Penn in "Daddio"

Directorial Work

Sean Penn's directorial debut came with "The Indian Runner" (1991) – a raw, authentic film, according to critics, about two brothers with completely opposite views on life. The movie starred David Morse and Viggo Mortensen.

In 1995, he delivered "The Crossing Guard" with Jack Nicholson in the lead role. After the premiere, The New York Times critic Janet Maslin wrote: "Mr. Penn is a heavyweight director, whether battering viewers with the obvious or hammering home the heartfelt and true."

In 2001, Penn released another impressive directorial effort – the drama "The Pledge". Once again, Jack Nicholson took the lead, this time playing a detective who vows to find a child's killer.

But Penn's real breakthrough as a director came with the biographical drama "Into the Wild" (2007). The protagonist – a promising graduate played by Emile Hirsch – rejects opportunity and sets off on a dangerous journey. The film earned Penn a Directors Guild nomination.

Sean Penn sitting on the ground filming a young man on a broken-down couch with a movie camera — Sean Penn on the set of Into the Wild

In 2023, Penn premiered his first documentary, "Superpower", at the Berlin Film Festival, centered on Ukrainian President Volodymyr Zelenskyy.

Sean Penn's Personal Life

After divorcing Madonna in 1989, Penn started dating actress Robin Wright. Their first child, daughter Dylan Frances, was born on April 13, 1991. Their second child, son Hopper Jack, arrived on August 6, 1993. The couple tied the knot in 1996.

Their marriage lasted until 2010. Later, Robin Wright told The Telegraph that she and Sean broke up and got back together multiple times, trying to keep the family intact for the kids. Penn was the stricter parent, but his demanding schedule kept him constantly away from home. "He'd come back and be the bad cop, and then leave, making me deal with the aftermath. I tried to soften the blow. We were two extremes," Robin recalled.

Sean Penn, Robin Wright and their children — Sean Penn and Robin Wright with their children

Both kids followed in their parents' footsteps. Dylan and Hopper appeared alongside their father in his film "Flag Day" (2021). Dylan shared that her mother convinced her to join the project with one simple argument: "I've never worked with a better director than your father." Penn himself called working with his children one of life's greatest moments: "I'm incredibly proud of her."

But it wasn't all smooth sailing. In a 2017 interview with ES Magazine, Hopper opened up about his struggle with methamphetamine addiction.

From 2013 to 2015, Penn dated actress Charlize Theron. In 2016, he got involved with Australian actress Leila George. They married in summer 2020, but the marriage lasted less than two years.

Sean Penn in a black jacket and Leila George in a beige sweater — Sean Penn and Leila George

In June 2023, Sean Penn started dating Ukrainian Olga Korotyayeva. She's from Cherkasy, 17 years younger than the actor, trained in acting in France, and performed at Paris's Théâtre de Paris.

Penn also tried his hand at literature. In 2018, he published a satirical novel about a hitman called "Bob Honey Who Just Do Stuff."

Sean Penn and Olga Korotyayeva walking down the street holding hands — Sean Penn and Olga Korotyayeva

Activism and Humanitarian Work

In October 2002, Sean Penn spent $56,000 to publish an open letter in The Washington Post to President George W. Bush, calling for an end to the Iraq War. Two months later, he personally visited Iraq to protest Bush's policies.

In September 2005, Penn headed to New Orleans to help victims of Hurricane Katrina.

In 2010, after a devastating earthquake hit Haiti, Penn and activist Ann Lee founded the humanitarian organization CORE (Community Organized Relief Effort).

Penn doesn't like calling himself an activist:

I feel more like a plumber. I don't want to talk to babies or sick kids or their parents, just tell me what's broken and we'll see if we can fix it.

Sean Penn

Since 2022, CORE has been operating in Poland, Romania, and Ukraine, helping Ukrainian refugees.

Sean Penn Now

One of 2025's major projects was Paul Thomas Anderson's "One Battle After Another", inspired by Thomas Pynchon's novel "Vineland". The film hit theaters on September 26, 2025.

In the film, Penn played the antagonist, Colonel Stephen Lockjaw. Critics called his performance outstanding: "His Lockjaw is simultaneously a terrifying monster and a pitiful fool, with an affected military gait that tells you everything about this man's bottomless inner insecurity."

Sean Penn in military uniform — Sean Penn in "One Battle After Another"

Penn's documentary about journalist Jamal Khashoggi was in production in 2025. According to him, it won't be just a retelling of events, but "a heartfelt tribute to the indomitable spirit of journalism, the relentless pursuit of truth, and the inevitable sacrifices."

Penn also appeared in "Gonzo Girl", directed by Patricia Arquette, based on Cheryl Della Pietra's semi-autobiographical novel about her experience working as writer Hunter S. Thompson's assistant.

Sean Penn: latest news and articles

Adam Bryan Johnson

I think Sean Penn is good to play the bad guys. His path is action movies and thrillers, definitely.

2021-05-18 18:36:44
Tara Wright

Sean Penn`s children are very beautiful!!! I wish him new achievements and heights in the acting field.

2021-05-12 10:12:35
Zachary Hayden Jackson

«Mystic River» is the case when everything is perfect. And the director, and the script, and the actors, and the idea itself! Sean Penn famously got used to the role of Jimmy Markum.

2021-03-29 11:20:27
Patricia Robbins

Sean Penn is not handsome, but in Hollywood films all kinds of actors are needed, right?

2021-03-28 22:50:26
Harold Edwards

A punchy man, I am inspired by his tenacity. I almost never miss a single film with him. My favorite roles are «I Am Sam», «21 Grams» and «The Secret Life of Walter Mitty».

2021-03-09 19:49:23

Sean Penn

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