The Life and Times of the Incorrigible Sean Penn

Comparisons of Sean Penn inevitably crop up, odious though they are. One can compare him to Errol Flynn, but Penn is in a class apart. He rose to stardom only for his career to nosedive. Then he resurrected like a phoenix, winning the Academy Award twice and reinventing himself as a character and an actor.

Sean Penn / Sean Penn / Madonna, Sean Penn / Sean Penn, Leila George.
Source: Getty Images

Penn was involved with many women over the years. He acted and directed and was also a well-known political activist and humanitarian as well as a writer. He found time to work for victims of Hurricane Katrina and founded the Haitian Relief Organization in 2010 after the Haiti earthquake. Penn then went on to visit flood-stricken villages in Pakistan. What drives him?

Sean Penn’s Childhood Years – a Peek into His Past

Penn was born on August 17, 1960, to Leo Penn and Eileen Ryan in Santa Monica, California. Chris Penn and Michael Penn were his brothers. Leo Penn was a director and Eileen Ryan was an actor.

A dated studio portrait of Sean Penn.
Photo by Images/Getty Images

Sean Penn went to Santa Monica High School. It was only natural that he should start making short films with his friends while still in school. This led to Penn taking part in an off-Broadway play. He learned acting from his parents, but his acting in the play earned him negative criticism from his mother.

Penn Learns Acting and Turns to Broadway

Penn had enrolled at the Santa Monica College to study auto mechanics but dropped out to apprentice with LA’s Group Repertory Theatre in the late 70s. He trained on the stage and that time was crucial in molding him as a multi-dimensional actor.

A photo of Sean Penn in a scene from Heartland.
Source: The New York Public Library

Penn made his debut in the Broadway production of “Heartland” in 1981. He was definitely making progress and would go on to become a star in his own right. He had help and support from his parents and friends and his own burning ambition to make it to the top.

Penn Acts in “Little House on the Prairie”

“Little House on the Prairie” is one of those TV shows that ran for an interminable length of time and saw various actors enter and exit as the show progressed. Penn’s father was a director of the television series and managed to land a role for his son as an extra in “Little House on the Prairie.”

A still of Sean Penn in Little House on the Prairie.
Source: YouTube

Penn did a few episodes that were directed by his father. Unfortunately, the script he was given and the storyline ensured that his role did not go further. Penn had to look for other work.

Penn Makes His First Film In 1981

Penn took his mother’s criticism to heart and set about improving his acting skills, looking for an outlet to showcase his talent. He got lucky and landed a role in a film in 1981. That film was “Taps,” followed by “Fast Times at Ridgemont High” in 1982.

A still of Sean Penn in Taps.
Source: YouTube

The next year, in 1983, he starred in another film, “Bad Boys,” in which he played the role of a teenage delinquent. His acting was appreciated, and he won the Los Angeles Film Critics Association Award. This was probably the steppingstone toward an illustrious career.

Penn Coins the Word ‘Dude,’ Which Passes Into Popular Lexicon

Today, no one gives much thought when using the term ‘dude,’ but one must know that it was his role as surfer-stoner Jeff Spicoli in “Fast Times at Ridgemont High” in which he used the word ‘dude.’ Eventually, it became a common word in popular culture.

A still of Sean Penn in a scene from Fast Times at Ridgemont High.
Source: Copyright: Universal Pictures

“Bad Boys,” released in 1983, also helped Penn to jumpstart his career as his work in the film earned him positive reviews. He played the role of a troubled young man in the drama “Bad Boys,” released in 1984, Penn played the role of a punk rocket burglar in “Cracker” and starred alongside Nicolas Cage in another film, “Racing with the Moon,” as a World War II marine.

Penn Falls for Elizabeth McGovern

Penn met Elizabeth McGovern, the “Downtown Abbey” star while filming “Racing with the Moon.” He fell for her, and the feeling was mutual, and they got engaged. They had a hectic time together as Penn actively pursued the relationship.

A promotional portrait of Elizabeth McGovern in Racing with the Moon.
Source: Copyright: Paramount Pictures

Penn proposed to McGovern when she was 23 years old. The relationship lasted for a couple of years but never culminated in marriage as McGovern opted out. She did not want to get married while he claimed he did. She found the relationship too exhausting, and they both wanted to do different things.

The Incorrigible Penn Weds the Inimitable Madonna

Not one to be put down or put off, Penn soon found another love, and this time it was Madonna, the great pop singer. They were married in 1985, and the marriage lasted just about four years until 1989. Surprisingly, Madonna claimed in 2016 at a charity gala at Art Basel that she still loved Penn.

A dated picture of Madonna and Penn walking the street.
Photo by Vinnie Zuffante/Michael Ochs Archives/Getty Images

There were rumors that Penn had allegedly assaulted Madonna in 1987 and 1989, possibly being the grounds for divorce. However, Madonna vehemently denied all such reports as being outrageous and false. The embers still smolder apparently.

A Turbulent Relationship Led to Divorce

It was not smooth sailing for Penn and Madonna. Penn was reportedly mentally unstable and had developed a drinking habit. He was sent to jail in 1987 for violating probation and assaulting an officer. He was also charged with reckless driving.

A dated photo of Madonna and Penn.
Photo by Ron Galella/Ron Galella Collection/Getty Images

Madonna later said in an interview with Rolling Stones that she had felt hostile towards him on account of her heart being broken by his behavior. However, in her heart of hearts, Penn was her one true love. Even to this day, she has a soft spot for Penn.

Flirting With Singer-songwriter Jewel

Penn saw a performance by singer-songwriter Jewel in 1995 on “Late Night with Conan O’Brien” and felt hugely attracted to her. Not one to let the grass grow under his feet, Penn phoned her at her family home to set up a date.

An image of Jewel performing during a festival.
Photo by Paul Natkin/Getty Images

Jewel’s dad told her that there was a prank caller on the line identifying himself as Sean Penn. Penn and Jewel did get together, but she was chary of becoming a star’s girlfriend. However, she liked the way he brought out the best in her and never ridiculed her.

Penn Finds Love in Robin Wright

Even as his Hollywood career took off, Penn found love in Robin Wright after he was divorced from Madonna. One thing led to another, and they got married in 1996. The marriage lasted a record 14 years before ending in divorce in 2010.

A photo of Sean Penn and Robin Wright attending an event.
Photo by Ron Galella, Ltd./Ron Galella Collection/Getty Images

Penn and Wright had a daughter, Dylan, in 1991, and a son, Hopper, in 1993, while they were married. Penn and Wright did not get along well as they held different views about parenting, and the divorce was not an amicable one. Still, Sean maintains a relationship with their kids. Penn is especially fond of his daughter, who would eventually go on to become an actress.

The Year Was 2011 and Scarlett Johansson Was the Flame of His Life

Barely a year after his divorce to Wright, Penn latched on to Scarlett Johansson. The couple was seen at a romantic getaway at Cabo San Lucas in Mexico, where they purportedly went after being spotted at lunch in Los Angeles. The question is: Would this be the start of a wonderful relationship?

A picture of Penn and Johansson during an event.
Photo by Dimitrios Kambouris/VF11/WireImage/Getty Images

The couple did put in a few public appearances, such as at the White House Correspondents’ Dinner Party in Washington DC in April 2011. They were sighted together a few times thereafter. However, by June 2011, it seemed the relationship was going nowhere, and it eventually fizzled out.

Penn Zeroes in On Charlize Theron

The incorrigible Sean Penn, though twice divorced, never gave up on romance. He started dating Charlize Theron in 2013. He even considered getting married to her, stating that it would a “first” marriage since the previous two were entered into when he was less informed. Really?

Sean Penn and Charlize Theron pose for the press.
Photo by Kevin Mazur/WireImage/Getty Images

The relationship, beautiful as it was, ended in 2015. Theron said that she was never going to marry him and that she got into a relationship when being directed by Penn in “The Last Face.” It was never serious, according to her. Poor Sean.

Then Came 2020, and Penn Ties the Knot with Leila George

Fast forward to July 2020, and Penn married the gorgeous Australian actress, Leila George, at an intimate ceremony at home. The marriage was the culmination of a long romantic association that started in 2016, a short while after Penn gave up on Theron.

A photo of Sean Penn and Leila George attending an event.
Photo by Kevin Winter/Getty Images

The stars held something different for these two stars. George filed for divorce from Penn in just a year’s time. Though divorced, they reunited later after a cooling-off period. It was a Covid-era marriage, a bright spot in an era of gloom.

Penn And George Spotted on Beach in Coney Island

Just one month after the divorce, Penn and George were spotted at a beach in Coney Island. They were in good spirits and Penn patted their pet dog, whom they had adopted in 2017. It seemed like they still enjoyed one another’s company.

A photo of Leila George and Sean Penn walking the street.
Photo by RB/Bauer-Griffin/GC Images/Getty Images

Penn was shooting his upcoming film “Black Flies.” George happened to be passing by, dressed in a gray sweat suit and light blue hoodie, a casual getup. George wore blue jeans and a navy-blue t-shirt. They had a good time with other members of the crew, including Jean Stephane Sauvaire and Tye Sheridan.

Sean Penn Admits His Mistake About Leila George

They married during the pandemic and had a lovely life for two years. However, the divorce took place due to irreconcilable differences. Penn blamed himself for the divorce. He should have known better at 61 years of age, but it seemed he was too busy with his professional life!

Leila George attends an event.
Photo by Gregg DeGuire/WireImage/Getty Images

He claimed he loved George and admitted that he had screwed up the marriage. Penn said that he had been neglectful, consumed with his obsession with alcohol, and was depressed. Perhaps George understood and forgave him, leading to a reconciliation. She is associated with Penn’s CORE non-profit organization.

Penn Turns to Directing and Makes His Directorial Debut

Does all this philandering mean that Penn wasn’t committed to his acting career? There certainly was a hiatus from 1985 to 1990. Penn then turned to directing, an area in which he would excel just as he had in acting.

A photo of Sean Penn behind the scenes.
Source: Copyright: MGM

Penn made his directorial debut in “The Indian Runner” in 1991. It was just the beginning of a successful career in directing. He followed that by continuing his acting career and starring in other great films, such as “Dead Man Walking” in 1994, and by playing a jazz guitarist in “Sweet and Lowdown” in 1999. He also starred in “I Am Sam,” where he portrayed a mentally challenged man.

“At Close Range,” a Watershed Moment for Penn

From 1981 to 1986, Penn had a pretty unbroken run as an actor, earning plaudits all the way. His 1986 film, “At Close Range,” earned him praise, but thereafter, there was a gradual decline in Penn’s acting career.

A promotional still of Christopher Walken and Sean Penn in the film.
Source: Copyright: Orion Pictures

“At Close Range” is a neo-noir crime drama based on the real-life crime family led by Bruce Johnston Sr. This film also featured Sean’s brother, Chris Penn, working alongside him. Penn was hailed as “probably the best of the younger actors” back then. However, Sean chose to lie low and, instead, forage into directorial territory.

More Directorial Successes for Sean Penn

A mercurial maverick and a non-conformist, Sean Penn directed eight films, each one a landmark, which was a testimony to his art and skills as an actor, screenwriter, and director. He debuted with “The Indian Runner” in 1991, followed by “The Crossing Guard” in 1995.

A photo of Emile Hirsch and Sean Penn behind the scenes of Into the Wild.
Source: Copyright: Paramount Vantage

That was just the start. It led to more films directed by Penn, including “The Pledge,” “Into the Wild,” “September 11,” “Flag Day,” and “The Last Face.” Some were lambasted; some acclaimed, but Penn had arrived on the directorial scene and made his mark. “The Pledge” earned critical acclaim, while “The Last Face” was trolled.

Penn Ups the Acting Ante

Even as he directed films from 1991 to 2016 and still considered new projects, Penn restarted work as an actor. He acted in “The Last Party” and “Carlito’s Way” in 1995, he starred in “Dead Man Walking,” a command performance by any means. “Dead Man Walking” was a particularly fine film showcasing Penn as Matthew Poncelet, a prisoner on death row in Louisiana.

A promotional still of Sean Penn in Dead Man Walking.
Source: Copyright: MGM

Susan Sarandon walked away with the Academy Award for Best Actress, and though Penn and Robbins were also nominated by the Academy for “Dead Man Walking,” they did not win those awards. However, Penn managed to win the Chlotrudis Award for best actor for this film.

More Films Starring Penn – Academy Award Nominations

The following years saw Penn mature as an actor and deliver some truly fine performances. 1997 saw the release of “Loved,” “She’s So Lovely,” “U Turn,” “The Game,” and “Hugo Pool.”

A still of Jennifer Lopez and Sean Penn in U Turn.
Source: Copyright: Sony Pictures

In 1999, Penn starred in Woody Allen’s “Sweet and Low Down” as Emmet Ray. His characterization of the role earned him an Academy Award Nomination. 2001 saw the release of “I am Sam” in which Penn portrayed a mentally challenged individual, a role that won him critical appreciation, firmly establishing him as a fine actor of his generation.

Penn Wins an Academy Award for “Mystic River”

Clint Eastwood directed the film “Mystic River,” released in 2003. Penn played the eponymous role of Jimmy Markum, an ex-con whose daughter is murdered and sets about planning his revenge. He brought to the fore all his acting talents in this film, depicting an individual torn between being a victim and a perpetrator.

A still of Sean Penn in Mystic River.
Source: Copyright: Warner Bros.

As he investigates the crime, Markum realizes his childhood friends may have played a role in the death of his daughter. Penn gave a powerful performance. He won the Academy Award for Best Actor for his role but was shy when it came to accepting it. However, he did and expressed thanks to everyone who made it possible.

Sean Penn Wins the Academy Award a Second Time for “Milk”

Penn portrayed Harvey Milk in “Milk,” a film directed by Gus Van Sant and released in 2008. Milk was an LBGTQ activist working for gays and lesbians in San Francisco’s Castro district in the early 1970s. This was a tour-de-force, stand-out performance by Penn.

A still of Sean Penn in a scene from Milk.
Source: Copyright: Focus features

The unparalleled performance by Penn as Milk led to his winning the Oscar for Best Actor for “Milk,” and he also received a 2009 Golden Globe nomination for the role. The film received Academy Award nominations in 8 categories and won two – one for best original screenplay and one for best actor in a leading role.

More Recognition for the Versatile Sean Penn

The success of “Milk” probably encouraged Penn to do even better. In 2010, he starred in “Fair Game.” Next was “Tree of Life,” released the next year, earning him awards at the Cannes Film Festival. Penn was not only a nationally acclaimed actor but also an internationally recognized one.

A promotional still of Sean Penn in Fair Game.
Source: Copyright: Summit Entertainment

Way back in 1985, Penn portrayed the role of Lee, a former drug dealer in the film “The Falcon and The Snowman.” He played the role of Andrew Daulton Lee. When Lee was rehabilitated, Penn hired him as his personal assistant to thank him for letting him play the role.

Penn’s Acting Work Continues

As they say, one thing leads to another. Penn saw a resurgence in demand and starred in “Gangster Squad” and “The Secret Life of Walter Lilly” in 2013. But his performances in these films were nowhere near what he delivered in the 2003 release “21 Grams.”

A still of Sean Penn in Gangster Squad.
Source: Copyright: Warner Bros.

In “21 Grams,” Penn played a critically ill mathematician, a role he portrayed with sensitive finesse in an understated way. Penn went on to act in the 2015 thriller, “The Gunman,” in which his performance was routine but still noteworthy. In 2016, he lent his voice to the animated film “The Angry Birds.”

Penn Arrives as an Author

Meanwhile, Penn was working on a novel, “Bob Honey Who Just Do Stuff,” which was published by Atria Books in 2018. This was a satirical novel telling the story of an international assassin working for a secret government program who goes about killing people with a mallet.

Sean Penn discusses his novel on stage.
Photo by Gilbert Carrasquillo/Getty Images

The book covers a broad canvas of spaces, from New Orleans to Sudan, and narrates the twists and turns in the life of Honey, a septic tank salesman turned assassin. Unfortunately for Penn, the book was not received well in some quarters, while writers like Salman Rushdie and Paul Theroux praised it.

The Humanist and Activist—Other Facets of Penn’s Personality

Most actors would be content to wallow in their fame and spend their spare time in lavish luxury. Not Penn. He was a vital activist right since the early days and as we will see, did more than what other actors do in these spheres.

Sean Penn speaks on stage.
Photo by C Flanigan/Getty Images

Since the early 2000 years, Penn was a vociferous activist. He was opposed to the election of George Bush. That did not deter him from engaging in quite a few humanitarian works, sparing time from his busy schedule. That trend continues and can be seen to this day.

Penn Rushes to New Orleans to Help Victims of Hurricane Katrina

Not one to just mouth words of sympathy, Penn rushed to New Orleans in the wake of Hurricane Katrina. He hired a boat and helped stranded people get to safety. He was hailed as a hero.

A photo of Sean Penn in New Orleans after the Hurricane.
Source: YouTube

Some decried it as a publicity stunt since he took along a team of photographers to document his efforts. Still, when all was said and done, he was waist-deep in muck, working tirelessly to help rescue people, which is more than what we can say about other people, let alone actors.

Penn Flies Off to Haiti to Help Earthquake Victims In 2010

When the 2010 earthquake devastated Haiti, Penn rose to the occasion, or, to be more precise, he flew to Haiti with supplies to help those afflicted by the disaster. He set up a plane, arranged supplies, and flew to Haiti to take part in relief efforts.

A picture of Sean Penn helping in Haiti.
Source: YouTube

There can be no doubt that even a plane load of supplies, woefully insufficient as it was, proved to be welcome for people who had no support. This is typical Sean Penn – a diehard do-gooder at heart. These humanitarian works showcase the warm side of Penn.

Penn Stays in Haiti for 9 Months in a Tent

While others would have been satisfied with delivering supplies a couple of times, Penn went even further. He stayed over in Haiti and coordinated with local authorities to set up relief camps and relief works. He was at it from morning to evening, day in and day out.

A photo of Sean Penn during an interview.
Photo by Liam Storrings

Penn remained unassuming and helpful, assisting authorities to commandeer the golf course to provide refuge to 60,000 displaced people. He worked tirelessly, handing out rations and coordinating with local authorities for relief activities, never proving to be overpowering, knowing full well that getting on the wrong side of authorities would have a negative impact.

Don Hardy Films Citizen Penn

Fortuitously, Penn came across Don Hardy, who was into directing documentaries sometime in 2005, and they found common ground based on social justice. Hardy was working on “Witch Hunt,” which had a theme similar to Penn’s “Dead Man Walking.” Penn helped Hardy and that turned around Hardy’s career. “Witch Hunt” premiered and brought fame to Hardy.

Don Hardy Jr. and Dana Nachman pose with Sean Penn at the Witch Hunt premiere.
Photo by Teresa Barbieri/Getty Images

Hardy approached Penn again in 2010, but this was when Penn rushed off to Haiti and Hardy saw Penn fly off in a chartered plane. Hardy asked Penn’s assistant if he would like to have his work documented, to which he said yes. Hardy followed Penn with his crew and started shooting.

Sean Penn Forms CORE

Hardy filmed Penn at work, coordinating a multitude of relief operations but always unassumingly and never overbearing in his relations with the authorities. He ran the Jenkins-Penn Haiti Relief Organization, which was later renamed CORE. Hardy conducted a marathon interview with Penn about his work in Haiti and that laid the foundation for “Citizen Penn.”

Sean Penn speaks onstage during a CORE Gala event.
Photo by Kevin Mazur/Getty Images

Hardy filmed Penn organizing relief with the 82nd Airborne, but the military people were suspicious of Penn’s motives. But he built trust. Hardy documented it on film. The film also shows Penn as not being focused as a hero. Hardy would continue to film Penn at work on various humanitarian activities right up to Covid 19.

Penn Tackles Covid 19 in Los Angeles

When Covid 19 struck and Los Angeles was badly affected, it was time for Penn to spring into action, which he did willingly. He focused on promoting testing and vaccination. In the meanwhile, he also worked to distribute masks through CORE, his organization.

Sean Penn attends an event.
Photo by Axelle/Bauer-Griffin/FilmMagic/Getty Images

However, Penn’s action, in this instance as in previous instances, always raised an outcry. Some volunteers complained that they had to work in substandard conditions, but Penn emphatically refuted such allegations. “Citizen Penn” eventually was featured on Discovery+. Penn deserves to have his life’s work, other than that of an actor, showcased before the world.

Penn in Ukraine During the War

Trust Penn to be where the action is. There were rumors of the impending invasion of Ukraine by Russia around February. Penn flew straight as an arrow to Ukraine and started filming a documentary in Kyiv when the invasion began. It was not opportunistic but born of a genuine desire to help.

A photo of Sean Penn during a press conference in Ukraine.
Photo by Ayhan Mehmet/Anadolu Agency/Getty Images

The inimitable and formidable Penn found himself, along with thousands of refugees, walking towards the Polish border, always at the risk of being attacked. Thankfully, he (along with others) crossed the border to safety. While in Ukraine, he visited Lviv where he met CORE co-founder and the city’s Governor, Maksym Kozytskyy.

CORE Working for Relief in Ukraine

Penn’s push and CORE’s feet on the ground helped to promote humanitarian efforts in Ukraine. He is also actively organizing donations for the Ukrainian people. At the same time, he is filming a documentary along with Vice Media. He went as far as to vow to “smelt” his Best Actor awards for “Milk” and “Mystic River.”

A picture of Sean Penn addressing the media at a conference.
Photo by Omar Marques/Getty Images

It seems Sean Penn is quite impressed by the Ukrainian President, Zelensky. On Fox News’ “Hannity,” Penn said, “In him, I saw something I’d never seen before.” He went so far as to say that Ukraine might win but at a great cost.

Penn’s Net Worth Gets a Boost

Penn can afford to be a philanthropist through his organization, CORE. His fame and riches allow him to indulge in humanitarian work. His net worth has been rising steadily since 2017.

A portrait of Sean Penn.
Photo by Samir Hussein/WireImage/Getty Images

In 2017, his net worth was estimated at $50 million. This climbed up to $55 million in 2018, and then $60 million by 2020, it was $65 million and by 2022, his net worth climbed to $70 million. Penn is not a billionaire by any means, but this is a man with a heart of gold.

Penn’s Property and Assets

Penn owns a few properties in Santa Monica, Los Angeles, Las Vegas, and New York. He has conveniently built a network of properties that suit his travel and work itinerary. Still, compared to what others own, his property can be termed as being reasonable for a multi-millionaire.

A photo of Sean Penn in his home.
Photo by Getty Images/Getty Images

Penn loves cars. He owns quite a few vehicles, including a Mercedes Benz, Mercedes GLX, Audi A4, Ford, and others like the Nissan Titan, Ford Mustang Shelby, and Aston Martin. As can be seen, Penn is not pretentious, not opting for a Maserati or Rolls or Bentley.

What Is Sean Penn up to These Days?

Penn’s recent production was the 2021 film, “Flag Day,” in which he starred alongside his daughter Dylan. Dylan, understandably, was nervous about working alongside her father, who had built up a reputation as a great actor. She was apprehensive and was hesitant to work, not knowing how it would go.

A photo of Sean Penn during an event.
Photo by Emma McIntyre/Getty Images

What made it all the more intimidating for Dylan was that Sean directed as well as acted in the film. Still, she found out that he was not quite as overbearing as she assumed he would be, and working with him turned out all right.

Sean Penn Stars with Julia Roberts in “Gaslit”

As stated above, Penn is actively filming a documentary in Ukraine these days. Prior to that, he worked on the “Gaslit” show along with Julia Roberts. This show is based on the Watergate story, but with a different take. It is a docudrama of sorts and is an 8-episode TV series created by Robbie Pickering.

A still of Sean Penn and Julia Roberts in Gaslit.
Source: Copyright: NBC Universal Television

Roberts wanted Penn as her TV husband partly because she claimed to have known him and because her husband Danny Moder, a cinematographer, had worked with Penn on “Flag Day.” Penn portrays the role of Nixon’s attorney general John Mitchell. Penn gave it his best shot, recreating the balding and overweight Mitchell look.