Two-time Academy Award winner Sean Penn is a Hollywood icon, having appeared in over 50 films across an incredible 46-year career.

Among his more unusual exploits are secret journalist missions, an on-set brawl over a mere photograph, and a foreign jailbreak. Here are ten facts you may not know about Penn.

20. He once interviewed El Chapo in the depths of the Mexican jungle

In 2016, the intrepid Penn sought out an interview with Joaquín ‘El Chapo’ Guzmán, a fugitive at the time, through his connection with Mexican actress Kate del Castillo.


Unbeknownst to authorities, Penn travelled through remote jungle in Mexico for a seven-hour chat with the drug lord.

Penn spoke to El Chapo about drug culture and jail breaks. When Penn asked El Chapo about violence, El Chapo denied that he was a violent man.


“All I do is defend myself, nothing more,” El Chapo told Penn. “But do I start trouble? Never.”

The story made a splash in Rolling Stone, which described El Chapo as “the most wanted man in the world.”


Penn described the interview as an “otherworldly experience of sitting with a man so seemingly serene, despite his living a reality so surreal.”

19. He once escaped a Macau prison on a jetfoil

When Penn and his then-wife Madonna travelled to Macau to film Shanghai Surprise, they attracted a massive media presence.


At one point, Penn even discovered a paparazzo hiding in their hotel room to catch shots of the couple.

Enraged, Penn dangled the man over their ninth-floor balcony, with the help of his personal assistant.


Penn and his assistant were promptly arrested for attempted murder, and thrown in a jail cell.

Bizarrely, the jailer momentarily left their cell door open, at which point the pair slipped out.


Penn and his assistant fled further arrest by taking a jetfoil to Hong Kong. The actor later received a pardon from the Portuguese Government.

18. After playing a real-life drug dealer in The Falcon and the Snowman, Penn hired the dealer as his personal assistant

Andrew Daulton Lee was a drug dealer who stole US state secrets and passed them on to the USSR in the 1970s.


His life and arrest formed the plot of The Falcon and the Snowman, with Penn portraying Lee.

After Lee was released on parole, Penn hired the former dealer for a short while as his personal assistant.


Penn has long been outspoken about how important it is to rehabilitate prisoners.

In 2013, Penn successfully pleaded for the release of businessman Jacob Ostreicher, who had been jailed in Bolivia without charge during a money-laundering investigation.


Ostreicher later said to the Associated Press: “If it weren’t for Sean Penn, I would be another statistic in Bolivia and I would die in prison.”

17. He once went to jail for punching an extra

Penn was filming Colors at Venice Beach in 1987 when movie extra Jeffrey Klein took a photo of him.


Penn swore and spat at Klein, who spat back. The star then punched Klein, leading to a 60-day prison sentence. Penn served 32 days in Mono County Jail.


This wasn’t Penn’s first visit to jail – he actually previously spent time in prison for a film role.


Bad Boys, a movie about juvenile delinquents, was the first film for which Penn received top billing – and the film’s realism was exactly what enticed the actor.

Penn spent a week filming his incarcerated scenes in a maximum-security youth reformatory in Chicago.


Among the actors and extras were around 30 real-life inmates, as well as their real-life supervisors.

16. He was once engaged to Bruce Springsteen’s sister

The Indian Runner, the first film written, directed and produced by Penn, is based on the Bruce Springsteen hit Highway Patrolman.


Penn was briefly engaged to Springsteen’s sister Pamela, with whom he starred in Fast Times at Ridgemont High.

Springsteen’s song follows the tale of two brothers – one hot-headed, the other conciliatory and caring.


Penn’s crime drama is set in Nebraska and follows the lives of a sheriff and his criminal brother.

During production, Penn felt that Viggo Mortensen, who was playing the criminal brother, was not quite intimidating enough – so he arranged for Mortensen to spend time with a Hells Angels member to develop a tougher persona.


In a review for the New York Times, critic Janet Maslin said that “loose, rambling and sometimes rudderless as it is, The Indian Runner has a fundamental honesty that gives it real substance.”

15. Robert De Niro inspired him to act – and now they share birthday parties

Penn credits Robert De Niro, 17 years his senior, with inspiring him to pursue a career in acting.


“It can be fairly said that Robert De Niro is the reason I became an actor,” Penn said at the AFI Lifetime Achievement Awards in 2003. “As was the case with almost every other actor of my generation, I was inspired by his invention, his discipline and the strength of his personal character as it transposed into those he played.”

While co-starring in We’re No Angels in 1989, De Niro and Penn actually developed a close friendship.


In this comedy, Penn and De Niro sport identical haircuts as two runaway convicts who disguise themselves as priests.

Funnily enough, the Hollywood pair share the same birthday – 17 August, in 1943 and 1960 respectively – and the two have since been known to enjoy shared birthday parties.


In 2001, their shared birthday party saw the pair blowing out candles together – but when a photographer allegedly “snuck into” the party to capture the moment, De Niro started a $1 million lawsuit against the photo agency.

14. He used to smoke four packs a day

Penn was famously a heavy smoker in his youth and has long struggled to quit.


On his 40th birthday, Penn pledged to stop smoking in an effort to protect his health.

Again, he tried to kick the habit while dating Charlize Theron, who reportedly asked him to not smoke around her young son.


Theron herself quit smoking following her three-pack-a-day habit, after she worked with a hypnotist.

But Penn later lapsed and shocked audiences by smoking during his live appearance on the Late Late Show with Steven Colbert in 2018.


In this interview about Penn’s new book Bob Honey Just Do Stuff, Penn smoked two cigarettes, and also spoke in praise of the recent Parkland shooting survivors.

13. His father was blacklisted during the Red Scare

Leo Penn, celebrated actor and director, felt the wrath of the McCarthy era when he expressed his support for unions.


Paramount ended his contract, ruining his career as a movie actor in the late 1940s.

Leo found work in television acting but was forced out after CBS heard an anonymous tip-off that he had spoken at a political meeting.


In 1974, Leo Penn directed several episodes of the TV series Little House on the Prairie.

Joining his father on-set, the teenage Sean Penn appeared as an extra in one episode, marking one of his earliest screen performances.


Sean’s late older brother Chris Penn was also an actor, with starring roles in Reservoir Dogs and True Romance, while his eldest sibling Michael Penn is a musician.

12. He was the top choice to play Superman in the early 90s

Jon Peters owned the rights to the Superman film franchise in the early 1990s, and he envisioned Penn taking the star role – but the character would be drastically different from past iterations.


Peters reportedly planned to strip away many classic elements: his Superman, for example, would lose the famous costume and wouldn’t fly.

Peters’ plans fell through, and the next film in the franchise was Superman Returns, starring Brandon Routh.


Penn has since said there are too many superhero films in Hollywood, and has shied from committing to such a project.

“There are some good movies made on that [superhero] stuff, let a few of them be made a year,” he said in a 2015 interview with Reuters.


“But I’d like to see this business not drown itself in superhero movies,” he added. When pressed on whether he’d play one in future, Penn said, “Maybe, if there’s a very funny one.”

11. He helped to rescue Katrina victims

During Hurricane Katrina in 2005, Penn travelled to New Orleans to support emergency relief work.


He personally took part in rescue missions, and according to Esquire Magazine he pulled “dozens” of victims from the floodwaters.

However, Penn met with criticism among the press that his assistance in the time of crisis was just a PR stunt.


He denied this, claiming to the press that he only travelled to the city to do “whatever I can do to help.”

Five years later, Penn founded a relief fund for victims of the Haiti earthquake, creating a refugee camp for 55,000 people.


Penn had never visited Haiti before the disaster – and in honour of his work, the President of Haiti named him the nation’s first ever non-citizen Ambassador-at-Large.


10. He lost his home to a wildfire in 1993

In 1993, a wildfire ravaged Malibu and set alight the affluent Carbon Mesa Road.


Among the properties that caught fire was Penn’s $4 million home, built in a decorative Spanish style.

The home previously belonged to the actress Olivia Newton-John, and was completely destroyed in the fire.


Penn, however, was philosophical about the loss of his family’s home, and said it was actually a freeing experience.

“Everything in life burned, except my family, and it was so liberating,” he said in an interview with the LA Times.


“I didn’t have a bad moment about it. It sort of reinvigorated my interest in a lot of things.”

9. He learned Krav Maga for The Gunman

Penn undertook a gruelling physical regimen to prepare for the 2015 action thriller The Gunman.


This film sees Penn star as a black-ops mercenary undercover in the Democratic Republic of Congo.

For this role, Penn trained in Krav Maga. This fighting system borrows from karate, boxing and wrestling.


It was created by Imi Lichtenfeld, a Hungarian wrestler who taught street fighting to young Jews in Czechoslovakia during the rise of the Nazis.

At a press event, Penn noted, “The Krav Maga style of fighting is something that I was interested in because I had seen it applied and knew that philosophically it was different. There was no root in sport. It was much more martial than art.”


Brad Pitt, Angelina Jolie and Daniel Craig are among the other stars to train in Krav Maga for their movies.

8. He once owned a Parisian restaurant with Johnny Depp and Mick Hucknall

Penn used to have part ownership of a fancy Parisian restaurant not far from the Champs-Élysées, shared with several other stars.


His co-owners included Hollywood stars Johnny Depp and John Malkovich, and British musician Mick Hucknall.

The restaurant was named Man Ray, named after the American artist known for his influence in Dadaism and Surrealism.


It was founded and managed by the French film producer Thierry Klemeniuk, at 34 Rue Marbeuf.

The site was formerly a cinema, and the restaurant was later renamed World Place and then Mandalay.


The restaurant enjoyed great success, and was known for bizarre menu combinations like tomato ice cream.

7. Madonna’s True Blue is about Penn

A popular indie band in the Netherlands left no room for confusion over their favourite actor when they named themselves simply Seanpenn.


The band performed at the de-Affaire Music Festival in the Netherlands in 2006 and released the EP Lilium in 2005.

Penn also provided musical inspiration to his then-wife Madonna in 1986, as she dedicated her album True Blue to him.


The album broke records as the first to ever reach number one in 28 countries worldwide.

It featured the song True Blue, in which Madonna sings about her feelings for Penn: “Your heart fits me like a glove.”


Penn and Madonna continue to support each other’s careers past their divorce, with Penn sitting front-row at his ex-wife’s Madison Square Garden concert in 2015.

6. He once disguised himself as a journalist in order to take a trip to Iran

In 2005, Penn visited Iran incognito to report for the San Francisco Chronicle on an upcoming election campaign.


He made notes while attending Friday prayers, and stayed in Tehran in a room looking out to the Elburz Mountains.

Credit: Telluride 749

Two years previously, Penn went to Baghdad, Iraq to visit a water treatment facility that was bombed in the Gulf War.


He met with hospitalized children and spoke with Saddam Hussein’s deputy advisor Tariq Aziz.

However, following his visit Penn complained that his words had been twisted by the Iraqi media, who reported Penn had “condemned the US-British threats to wage war against Iraq” on his trip.


His spokeswomen commented that this reporting was “specifically propaganda” and “a twisted interpretation of what he said.”

5. He has described the Academy Awards as ‘petty’ and ’embarrassing’

Penn has won two Academy Awards for Best Actor: in Mystic River and Milk.


But he has low opinion of the event itself and the press coverage of it.

“The horror of the Academy Awards is what the press does leading up to it, to make it a popular TV show,” he said in an interview with the Associated Press.


“They’ll actually make it like it’s an arm-wrestling event between two actors.”

“That becomes very petty,” he noted, “and that’s something that’s embarrassing to follow up with accepting the invitation to the party.”


While accepting his award for Mystic River, Penn opened his speech with a joke about the search for Weapons of Mass Destruction in Iraq – and was met with stony silence.

4. He loves to surf

Penn is an accomplished surfer – and has shown off his moves in two of his films to date.


In Fast Times at Ridgemont High, he plays Jeff Spicoli, a surfer with dreams of stardom.

To sink his teeth into this role, Penn pushed the other actors with his wild improvisations, and wouldn’t answer to any name other than Spicoli on-set.


At one point in The Gunman, his character lets off steam as he goes to surf.

In 2010, Penn was hoping to produce and star in a biopic about the surfing legend Dorian ‘Doc’ Paskowitz, and even met with him to run through his story – but the plans never reached fruition.


The star is also reportedly a big fan of paddle boarding and jet skiing.

3. He struggles to socialise since quitting alcohol

Despite his prolific Hollywood career, Penn says – perhaps surprisingly – that he is fundamentally a “shy” person.


Since quitting alcohol, Penn says he finds it harder to socialise at parties, and is often uncomfortable in big groups.

“This might be the last thing anybody would see, but I’m probably shy,” he said in an interview with Oprah in 2005. “I’ve never gone to a party where I didn’t drink alcohol. I have a great time, but I’m not comfortable.”


“I think I’ve learnt how to carry on a short time as though I’m not shy, based on remembering how I behave when I’ve got a lot of alcohol in me,” he noted to The Times in 2005. “But it’s never been comfortable.”

“I still can’t go into a crowd sober. You know that saying, ‘You are always loneliest in a crowd?'”


“Well, I would call a crowd anything but my six closest surfing buddies, my family.”

2. He directed music videos for Shania Twain and Jewel

For Shania Twain’s song Dance with the One That Brought You, Sean Penn was hired as the director of the music video.


Filmed in Los Angeles in 1993, the film follows a narrative about a couple dancing in a bar over the decades, and features flashbacks in black-and-white contrasting with “modern” scenes in full colour.

Charles Durning stars in the video as the male love interest, while the dancer Lois Kaplan plays his wife.


Penn talent-spotted Kaplan while she was performing at the Californian dance hall In Cahoots.

Jewel similarly hired Penn to work on a music video, for the folk-pop song Juan Patino Radio Mix, a version of the song You Were Meant for Me.


Penn and Jewel were in a relationship from 1995, and he even accompanied the singer on tour.

1. He’s worked with eight Oscar-winning directors

Among the Oscar-winning directors Penn has worked with are John Schlesinger and Oliver Stone, in the Falcon and the Snowman and U-Turn respectively.


Penn has also been directed by Woody Allen in Sweet and Lowdown, for which Penn was nominated for Best Actor.

Kathryn Bigelow, who made history by being the first woman to take the Best Director Oscar, also directed Penn in The Weight of Water, a French-American mystery film.


Clint Eastwood, Alejandro Iñárritu, Sydney Pollack and Barry Levinson take Penn’s total Oscar-winning directors to a total of eight.

When Penn’s friend Bradley Cooper missed out on a nomination for Best Director for A Star Is Born, Penn expressed his frustration in an article for Deadline.

“In a fair world, A Star is Born sweeps the awards,” he wrote. “It’s just such a gift. Clear minds and hearts cannot possibly deny it its due. It’s over and over again one of my favourite films of all time.”