Sean Penn makes headlines as an outspoken activist, a paparazzi puncher, and a general pain in the behind. He’s also bedded some of Hollywood’s most glamorous stars. So, which is it? A colossal tool of a human being or the Don Juan of Hollywood? Let’s take a look at 50 truth-baring facts that will help you decide for yourself.
1. He Was An Uncredited Kid
Sean Penn got his rather unspectacular show business start as an extra on the family drama Little House On The Prairie—mainly because his father was the director. He was a Hollywood kid through and through, and he went to Santa Monica High school alongside other future stars like brothers Emilio Estevez and Charlie Sheen.
With all this star potential around him, it wasn’t long until he got his first big break.
2. He Popularized A Slang
After appearing in the star-studded film Taps with Tom Cruise, among others, Penn went on to act in the teen cult classic Fast Times At Ridgemont High. Because of this film, some say Penn’s stoner character, Jeff Spicoli, helped popularize the term “dude” in contemporary culture. Thanks Sean—I think.
Fast Times at Ridgemont High (1982), Universal Pictures
3. His First Love Left Him
While shooting coming-of-age drama Racing With The Moon, Penn met Elizabeth McGovern. The two fell in love almost immediately and even got engaged—but their union was doomed to a heartbreaking end. Penn was already getting started with his bad-boy ways and refused to do any press for the film. Maybe this was a clue for McGovern, who quickly broke off the engagement and headed to New York City.
4. He Met A Material Girl
In 1985, Sean Penn happened to be on a Hollywood set when he came across a young woman making a music video. He became intrigued and decided to pursue her. Of course, this Material Girl was Madonna, who was just becoming famous as a pop star. Something ignited between the two of them—and it would make headline-grabbing fodder for the next few years.
5. He Ruined His Wedding Day
Penn and Madonna got married on her 27th birthday. Instead of enjoying the lovely ceremony, Penn spent his time shooting at the press in helicopters that were circling their outdoor wedding. He later pinned down a journalist who had arrived without an invitation. Penn highly valued his privacy—and would even ruin his wedding day to get it.
6. He Was A Control Freak
When Penn got called a paranoid control freak—by Madonna no less—it must have been a wake-up call. I mean, isn’t Madonna known for demanding complete control over all aspects of her work? If she’s saying you're a control freak, you’ve got to take a good long look at yourself. However, she also said a lot of nice things about her guy.
7. He Was The Coolest Guy In The Universe
In spite of all Penn’s hijinx at the wedding, Madonna was completely smitten with him. She dedicated her album True Blue to Penn and in the liner notes called him the “coolest guy ever.” What was behind Madonna’s adoration and almost obsessive feelings toward Penn? Well, he was sort of part of her family.
8. He Was A Father Figure
Once Madonna’s brother Chris Ciccone got a good look at Penn, he made a disturbing realization. Penn looked just like Madonna’s father as a young man. Chris also noted that Penn’s bad boy rebel attitude was just like their brothers’ behavior. This led brother Chris to conclude the relationship would be a disaster…and the press seemed to share the sentiment.
9. He And Madonna Weren’t Exactly Adored As A Couple
With almost daily news about Penn and Madonna’s privileged and at times repugnant lifestyle, The Daily News saw fit to dub them the ''most offensive people on the entire planet.” Wow, that’s got to hurt even the most self-absorbed megastar. Years later, the press toned down the moniker to simply call them: “The Poison Penns.” There, is that better?
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10. He Had An Odd Hero
Sean Penn had two hobbies, drinking, and brawling. And his hero, writer Charles Bukowski, was certainly an inspiration for these. But it wasn’t just the writer’s literary talent that Penn adored. It was Bukowski’s liver and kidneys. You see, according to Penn, Bukowski could get intoxicated every night and still function. Regarding the brawling…well, that just came naturally.
11. He Punched A Lot Of People’s Lights Out
The years following Penn’s marriage to Madonna found Penn using his fists—a lot. He seemed to find the excitement his relationship created in the industry a tad annoying, so he proceeded to rough up paparazzi and journalists. He even punched out an extra on his film Colors when the poor guy tried to secretly take his picture. Well, hitting photographers is one thing, but then he went a step further.
12. He Hit A Co-Star
Sean Penn was on the set of the film Casualties of War with co-star John Leguizamo and the script called for Penn to knock some sense into Leguizamo’s character. Penn did not seem familiar with the skill of a stage hit, and proceeded to repeatedly slap Leguizamo in the face. After the 13th take, Leguizamo’s face was ballooning and no one could hear his lines. He was just short of quitting the film, when the director asked for one more take.
Casualties of War, Columbia Pictures
13. He Avoided Using His Fists, But It Ended up Being Worse
With all the punching around Penn was doing, it wasn’t surprising when he turned to other resources for his problems with photographers. After all, his knuckles must have started to hurt. Penn’s solution to his paparazzi problem was absolutely disgusting. He bought a water pistol and fill it with his own urine. Luckily he never had to spray anyone: just threatening the paparazzi with it did the trick.
14. He Went To Prison
Eventually all of Penn’s altercations—with pretty much anyone who angered him—came to a head. He struck a photographer and got a prison sentence of 60 days. Penn served half of his sentence and was set free to make a film in Germany. But if you think he got off too light, don’t forget that he had an angry wife waiting for him outside.
15. He Battered Madonna
When Madonna picked Penn up from prison, she was already in a state. You see, before Penn did his time in prison, he’d allegedly hit the pop star with a baseball bat. Madonna didn’t press charges, since Penn he was already headed behind bars. But when she picked him up, he was in for some more punishment. Once they got in the car they had a shouting match and Madonna kicked Penn out onto the street.
16. He Had A Strange Set Of Priorities
Throughout all the drama between Penn and Madonna, there was also much love. Penn has gotten himself involved in many political issues over his years in the spotlight and yet he said about Madonna: "No movie, nothing is as important as her. No whale, no nuclear war, no starving nation is more important.” Well, that’s a weird way of putting it…and he certainly had a strange way of showing it.
17. He Held His Wife Captive
When Madonna filed for divorce, Penn’s reaction was chilling. He lost it and broke into their Malibu home. Inside the home, Penn allegedly tied Madonna up, threatened to cut her hair, and generally roughed her up. This went on for many hours—with Penn only taking a break when he went out to buy more booze.
18. He Had Trouble Letting Go
Penn finally let Madonna go, but only after she promised to do something indecent. Sadly, her nightmare wasn’t over yet. When she was driving away, he tried to attack again. She finally drove to the safety of Lieutenant Bill McSweeny who later said, after seeing her: “I hardly recognized her as Madonna. She was weeping, her lip was bleeding and she had obviously been struck.”
This altercation should’ve ended with Penn back in prison—but sadly, that’s not what happened.
19. He Got Off Lightly
Madonna continued with her divorce proceedings, but dropped the assault charges. Even many years later, she claimed that none of the assault ever happened. So, what was it that sent the young pop star crying and with a bleeding lip out into the safety of Lieutenant Sweeny? I guess we’ll never know.
20. He Moved On From Madonna Quickly
Penn didn’t take any time to reflect on his behavior with Madonna. Instead, he hitched up with actor Robin Wright, who he met on the set of the thriller State of Grace. Maybe life with Penn would prepare her for work with disgraced actor Kevin Spacey in House of Cards years later. Or maybe Penn had turned over a new leaf…
21. He Became A Father Figure—For Real
Penn seemed determined to have a more traditional relationship with Wright than he’d had with Madonna—and that meant kids. Soon a girl named Dylan Francis was born, followed by a boy. They named their son Hopper Jack, after family friends Jack Nicolson and Dennis Hopper. Hmmm, does anyone think that name is sort of ominous?
22. He Was On A Break!
Two years after Penn’s son was born, Penn and Wright had a trial separation that sent Penn, like Friends’ Ross Gellar before him, into the arms of another woman. Penn saw Jewel on Conan O’Brien’s show and called her up to ask her to write a song for a movie he was working on. Jewel’s father thought it was a crank call but eventually put it through to Jewel, who was immediately smitten.
23. He’s A Fantastic Flirt
Jewel was very impressed with Penn’s flirting skills and described him as a persistent and inventive suitor. Even more impressive was his promise to quit drinking while dating Jewel—which must’ve been a herculean challenge for the heavy-drinking Penn. All evidence suggests that Penn was turning over a new leaf regarding his respect for women. What he did next for Jewel sealed the deal.
24. He Went On The Road For Love
During their relationship, Penn put his own life on hold and became a very unofficial roadie on Jewel’s tour. It was at a time when her career was uncertain and Penn helped her a lot. Jewel wisely didn’t want the press to know who her new boyfriend was, and kept it totally under wraps. With no paparazzi to antagonize Penn, the two had ample time to fall in love. But Jewel shouldn’t have got too comfortable with the bed-hopping Penn.
25. He Could Be Quite Chivalrous
Penn got himself dressed up to attend the Academy Awards where a certain statue was on offer for his work in Dead Man Walking with Susan Sarandon. Before Penn even got to the ceremony, he found out that Wright was in a hospital emergency room. His reaction was completely unexpected. Without a thought for his potential Oscar—or his girlfriend Jewel—Penn headed to the hospital to be at Wright's bedside.
26. He Made The Wright Decision
Penn had impressed Wright with his drop-everything hospital visit, and the two reconciled. Jewel was quickly dispatched and Penn and Wright decided to tie the knot. The kids would now have a married father and mother—with Wright even adding Penn to her last name—and life would be normal. But with Penn, this Princess Bride should never have expected a happy ever after.
27. He Relieved Himself In Front Of A Crowd
In an infamous anecdote, Penn was once being interviewed for Rolling Stone magazine. The venue was, some may say appropriately, a bar. Penn was drinking heavily and was just too lazy to get up and go to the washroom. Rolling Stone journalist Chris Mundy watched as Penn took two bottles from the table and filled them with his own urine. The crowd at the bar laughed, and the interview continued.
28. He Left A Fellow Actor Out In The Cold
Penn was shooting the star-studded WWII action drama The Thin Red Line in Australia and a prank battle broke out between Penn and Woody Harrelson. Penn sent out 2,500 flyers announcing Woody Harrelson Day in a nearby town where Harrelson would sign autographs for $10. Later in the prank feud, Penn left Harrelson 40 miles into the Australian outback with no food, water, or way to get home.
29. He’d Do Anything For His Kids Approval
When Penn appeared on TV’s Friends, it took his fans by surprise. The bad boy Hollywood star and the saccharine smiles of the Friends cast didn’t seem like a likely combination. So why did Penn do it? It was actually for a heartbreaking reason. He wanted to impress his kids. The whole Penn family were fans of the show and even visited the set on occasion. Penn wanted the kids to see their daddy on the small, and to their eyes, more important screen.
Friends (1994–2004), Warner Bros. Television
30. He Traded His Fists For A Pen
When the creators of the South Park franchise suggested, in their satirical movie Team America, that it was okay for Americans not to vote, Penn got angry. A younger Penn might’ve used his fists, but wiser Penn learned to use his words—albeit a strange collection of words. The former pugilist somehow managed to use the words “cross-dressers”, “disembowelment” and even “ alas” in the short letter that chastised Trey Parker and Matt Stone. Somehow the fists seem less offensive.
31. His Wife Got Car-Jacked
Penn was no stranger to danger on and off-screen, but when his wife Robin Wright Penn and their kids got carjacked in LA, Penn started to get nervous. A teenager had threatened Wright and the kids with a hidden weapon. Wright gave over her keys and the thief sped away. No one got hurt, but Penn and Wright decided to move out of the neighborhood where it happened, and into the Bay Area.
32. The Couple Waffled In The Bay Area
Penn and Wright were now living safely in the Bay Area. However, they weren’t safe from each other. For unknown reasons they jointly filed for divorce in December 2007—but the story didn’t end there. Several months later, however, they sought a court dismissal of their divorce case. Something wasn’t right in the household and, given his history, I’m inclined to blame Penn.
After all, he had some strange habits.
33. He Kept Fit In An Unhealthy Way
When asked about his exercise regimen, Penn gave a surprising answer. He said: ”There are times when I'll go eight months every day [to the gym]. And then there are times when I'll be down at the bar for a couple of hours every day for eight months; it depends.’” Okay, it’s not the best fitness routine I’ve heard of, but what about food? Surely, he was on task on diet.
34. It’s Not Exactly A Breakfast Of Champions
Penn doesn't talk much about what he eats, more about where he eats it. He likes bars “where they'll serve you breakfast at the bar.” First question: what are you doing at a bar at breakfast time? He goes on to say that his favorite line in the world to hear is: “'Mr. Penn will have his breakfast at the bar.' That was the moment when I felt successful in life.” So winning an Oscar? Not so much.
35. He Milked His Gay Role
Speaking of winning an Oscar, Penn probably knows that nothing impresses the Academy more than actors heading into uncomfortable territory. This could be the reason why macho Penn chose to appear in Milk as Harvey Milk, America’s first openly gay man elected into office. But what Penn had to do to get through an uncomfortable scene is beyond normal.
36. He Had An Issue With A Romantic Scene
Harvey Milk, Penn’s character in 2008’s Milk, had a boyfriend played by James Franco in the movie. Everyone agreed that it would seem a little unbelievable if they never kissed in the film. The only problem was that Penn had never kissed a guy before. Penn and Franco felt a lot of stress gearing up to the big kissing scene, but it was Penn who came up with a strange solution to soothe his nerves.
37. He Tensed Up Before A Very Public Kiss
Word got out in San Francisco that there was going to be a very public on-screen kiss between Hollywood hunks Penn and Franco. Thousands of excited onlookers filled the Castro—San Francisco’s gay neighborhood—all to watch these two stars lock lips. Penn, who’d punched photographers and shot at helicopters, was as nervous as a teenage girl for his first man-on-man kiss. So what did he do as Franco’s moist lips came toward his? He said a prayer and thought of Madonna.
38. He Popped His Cherry
Once he and James Franco had swapped saliva, Penn’s next move was…surprising. He took to his phone and immediately texted Madonna to tell her what had happened. He said: “I just popped my cherry kissing a guy. I thought of you. I don't know why.” That’s a hall of famer when it comes to unsolicited ex texts. But, as you can gather, Penn somehow always lands on his feet, and that’s just what happened here.
39. He Shouldn’t Have Played Gay At All
While Penn’s work on Gus Van Sant’s Milk was a huge critical success, some found offense in him playing a gay character at all. You see, Penn had previously been supportive of the communist regime on the island nation of Cuba, where the government’s policies toward the LGBT community had been particularly abusive. This fact didn’t deter the academy, who gave him a nod for Best Actor.
39. He Made A Glaring Omission At The Oscars
It turned out that kissing Franco equaled an Oscar nod for Penn. On awards night his nomination became a win, and Penn was soon at the podium where he mostly said all the right things. Mostly. In his three-minute speech he mentioned a lot of people, however, he forgot to acknowledge one very important person: his wife. Did I mention he’d even brought up a list?
But Penn wasn't finished with his night yet—there was still the after party.
40. He Was On An Oscar Insult Roll
After winning the Best Actor Award, Penn was holding court at the Vanity Fair after party. Madonna, who had just been through press purgatory for adopting an infant from Africa, was in attendance with her younger boyfriend-of-color Jesus Luz. When Madonna approached Penn to offer congratulations, he took one look at Luz and said: “Another kid already?” Bam!
41. He Filed For A Non-Divorce
When Penn didn’t mention his wife’s name in his Oscar thank yous, it was a big indication that something was wrong with the Penn-Wrights. Given Penn’s bad rep with women, I’d generally blame him—but not so fast. It wasn’t Wright Penn who filed for the next set of divorce proceedings, it was Penn himself. He did, however, in true Penn fashion, cancel them a few months later.
42. He Got Served
Later that same year, Robin Wright Penn did file for divorce and—surprise surprise—she actually went through with it. July 22, 2010, marked the day that Sean Penn and Robin Wright Penn were no longer married. If you think this wasn’t the end of this chapter, something Wright Penn did make sure that it was.
43. She Dropped His Name
When Robin Wright Penn was truly done with Penn, she did something to make it even more official than divorce. She dropped Penn from her name. Wright had taken it on when they’d gotten married and now wanted to strongly signify that they were absolutely over for good. Did this make Penn angry? Let’s say…maybe?
44. He Had To Deal With His Anger
Penn was soon back to his old ways. You know, the usual kicking photographers and breaking cameras. This time he got sentenced to 300 hours of community service and a 36 hours of training to deal with his anger. Something tells me that hosting an anger management course with Penn might appear on the “worst jobs ever” list. But Penn was soon over it, and continuing on his own version of the Blond Ambition Tour.
45. He Has More Fun With Blondes
Has anyone else noticed that, since dating Madonna way back when, all of Penn’s major romances have been with blondes? Maybe Penn was still a little hung up on the platinum Material Girl. Whatever the reason, right after ending a short relationship with Scarlett Johansson (also blonde), he went for fair-haired Charlize Theron next.
The two dated for a year before Theron decided that Penn wasn’t father material. Wait, it took a year?
46. He Made A Bad Green Card Joke
Meanwhile, back at the Oscars, Penn was brimming with insults. When handing over the statue to Alejandro Gonzalez Iñárritu, the Mexican director of Best Picture Oscar winner Birdman, Penn made an absolutely reprehensible “joke.” He wondered aloud who had given the director a Green Card. Both Penn and Iñárritu claimed it was an inside joke, but others called out Penn for his cultural insensitivity.
47. He Interviewed The World’s Most Wanted Man
Penn’s next culturally insensitive moment came when he had an interview with Mexico's most notorious gangster, El Chapo. Penn says it was to open the conversation on the war on drugs, and followed it up with an article in The Rolling Stone. But what happened after the article came out put Penn’s life in danger.
48. He Made A Very Dangerous Enemy
The same day that Penn’s article about El Chapo came out, Mexican authorities apprehended the cartel kingpin—but what they said about Penn must have made him sweat. The attorney general of Mexico said that Penn had helped them locate El Chapo and was essential in his capture. Yikes. Doesn’t that make Penn enemy number one to the leader of one of the biggest cartels in the world?
49. He’s Afraid For His Life
Penn’s lawyers tried to stop a Netflix documentary about his meeting with El Chapo, saying that it puts Penn’s life in danger. Penn and his lawyers are afraid that the documentary will further point to Penn as an accomplice with the Mexican authorities and their takedown of the notorious kingpin. Penn failed to stop the documentary, and it’s now available for viewing. But this didn’t steer Penn away from controversy.
50. He Called Out A Movement
So what does Penn do when he’s not aggravating drug lords? Why, he’s taking swipes at women. Penn calls the #MeToo movement “not intellectually honest” and “a movement led by mania.” This is a particularly unpopular position to take—even for Penn. But there’s something about Penn that feeds on negative publicity. That could be the only reason he wrote a book.
51. He Wrote Something Resembling A Book
Some may call it random words on a page, while others might even call it ”repellant and stupid on so many levels.” Either way, critics gave Penn’s satirical novel Bob Honey Who Just Do Stuff abysmal reviews, and others called it out for its sexism. The book ends with a poem defending #MeToo casualties Charlie Rose and Louis CK. How did this guy find two women to marry him? Oh wait, he didn’t stop there…
52. He Had A Covert COVID Wedding
Amid the tragedy that was 2020, Penn married his third (occasional) blonde, Leila George. She’s an Australian-American actor who’s the child of Greta Scacchi and Vincent D. Onofrio—which makes Penn’s father-in-law only one year older than he is. The two lovebirds tied the knot quietly over Zoom. But first, one assumes that his young bride had to teach her older groom how the app worked. Mazel?
Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24
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