Sean Penn Has Always Been Hollywood's Biggest Psycho

Jonathan Sherman
Updated April 22, 2024 49.0K views 12 items

Sean Penn is one of Hollywood's most admired actors when it comes to his talent, but when his personal life is called into question it is quite a different story. Throughout his career, Penn has made news for all of the wrong reasons - particularly for being a totalĀ ass. In 2018, he was widely condemned for smoking on a Late NightĀ appearance. However, considering the actor's track record of violent behavior, that's pretty mild. PennĀ is known to be an actor and director who can be a nightmare to work with, and some of these true Sean Penn stories are simply terrifying.Ā 

From his infamous run-ins with the lawĀ to his history of violent behavior, these nightmarishĀ stories about theĀ infamous Hollywood bad-boyĀ cannot be missed.

  • He Allegedly Beat His Ex-Wife, Madonna, Nearly To Death

    He Allegedly Beat His Ex-Wife, Madonna, Nearly To Death
    Video: YouTube

    For many, this 1988 incident is when Penn went from being a bad boy to just being a bad person.

    The story was first brought to the public eye after Penn filed a defamation lawsuit against director Lee Daniels. Daniels mentioned Penn when he was defending actor Terrence Howard, stating, ā€œ[Terrence] ain't done nothing different than Marlon Brando or Sean Penn, and all of a sudden he's some f*ckin' demon.ā€

    While Madonna defended her ex-husband saying, ā€œSean never struck me, ā€˜tied me up,ā€™ or physically assaulted me, and any report to the contrary is completely outrageous, malicious, reckless, and false,ā€ skeptics point to the fact that reports do in fact exist stating that Madonna called the police on Penn in 1988. Lt. Bill McSweeney of the LAPD even admitted, ā€œI hardly recognized her as Madonna. She was weeping, her lip was bleeding, and she had obviously been struck.ā€

  • He Hit John Leguizamo On The Set Of Casualties Of War

    He Hit John Leguizamo On The Set Of Casualties Of War
    Photo: Columbia Pictures

    Penn is known to take his roles very seriously, but in his 1989 Vietnam War flick, Penn took his methods a bit too far, almost forcing actor John Leguizamo to quit. As Leguizamo told Hollywood.com:

    ā€œ[When] my character refuses and Seanā€™s gotta slap me into submission, and of course, Sean doesnā€™t believe in stage combat because heā€™s too method for that sh*t, so heā€™s slapping me for realā€¦ Weā€™re on the 13th take and my face [is] out to here and you canā€™t even understand the dialogue Iā€™m saying and [director] Brian de Palmaā€™s going, ā€˜We have to do it one more time, John, it was out of focus.ā€™ So itā€™s ā€˜whackā€™ and ā€˜whackā€™ and Iā€™m about to quit and then they cut the scene out of the movie.ā€

  • He Blew Up On A Fan Who Took A Picture Of Him

    He Blew Up On A Fan Who Took A Picture Of Him
    Video: YouTube

    Throughout his career, Penn has been an A-list star who apparently hates the spotlight, which is always a rather strange mindset for a world-renowned celebrity to have. And that state of mind was on full-display when he caught a fan snapping an unapproved pic of him. Apparently, catching Penn off guard is a terrible idea, as this fan learned when Penn turned to him and aggressively exclaimed, "Do we look like f*cking zoo animals?... I'll make you eat the phone... Get the f*ck out of here. Get out of here!" Alright, Sean, message received.

  • He Urinated In Front Of A Rolling Stone Journalist

    He Urinated In Front Of A Rolling Stone Journalist
    Photo: YouTube

    In a 1996 Rolling Stone article titled, ā€œSean Penn: Cool Jerk,ā€ journalist Chris Mundy describes how he was witness to some very strange behavior when Penn decided it was unnecessary for him to go to the bathroom to, well, go to the bathroom.

    Mundy recounts the strange interaction:

    ā€œHe recites jokes, he tells stories, he finishes urinating. Almost. ā€˜I need another bottle,ā€™ says Penn. He sets the brimming vessel in front of him, and the room erupts with laughter. He of the enormous bladder grins, and a second bottle is placed in his left hand before it quickly disappears under the tablecloth... Relief.ā€

  • He Pulled A Horrible Prank On Woody Harrelson

    He Pulled A Horrible Prank On Woody Harrelson
    Photo: 20th Century Fox

    Woody Harrelson and Sean Penn have been engaged in a legendary prank war, but Penn put that to an end when his prank on the set of You're Only as Good as the Next One could have easily left Harrelson dead. According to IMDb:

    "After driving 40 miles into the rustic outback of Australia, where their movie was being filmed, Penn pretended to get stuck and Harrelson got out to push. Medavoy says, 'Sean slammed it into four-wheel drive and literally left Woody in the dust, stranded, in the middle of the night, with no food, no water, and no way home except on foot. Woody was eventually picked up by an extra on his way to work.'"

  • He Attacked A Film Extra

    He Attacked A Film Extra
    Photo: Orion Pictures Corporation

    In 1987, Penn was working on the set of Colors when background actor Jeffrey Klein tried to sneak some photographs of Penn and co-star Robert Duvall. Unfortunately for Klein, his attempts did not get past Penn, who proceeded to punch him several times and only stopped when he was physically pulled off of Klein. Penn was sentenced to 60 days in prison, but ended up only serving a little over 30 days for his violent outburst.

  • He Was Caught Driving Drunk

    He Was Caught Driving Drunk
    Photo: Rita MolnƔr / Wikimedia Commons

    In 1987, Penn was pulled over while driving erratically and was found to have a blood alcohol content of .11 - that's .03 over the legal limit. And to make matters worse, thanks to Pennā€™s wealth and fame, his blatant DUI was reduced to reckless driving.

  • He Assaulted A Paparazzo

    Given his violent reputation, itā€™s no surprise that Penn would overreact when suddenly confronted by a professional celebrity photographer. In 2009, Penn agreed to 36 hours of anger management and 300 hours of community service after pleading no contest to assaulting paparazzo John Dawes.

    Dawes also received an undisclosed settlement, to which his lawyer said, "All of the net proceeds of the settlement will be donated to charities that support victims of domestic violence and victims of the earthquake in Haiti." This statement was seen as Dawes thumbing his nose at Penn, who had been an outspoken advocate for the crisis in Haiti.

  • He Interviewed A Murderous Drug Kingpin

    He Interviewed A Murderous Drug Kingpin
    Video: YouTube

    Pennā€™s 2016 interview with Mexican cartel boss, El Chapo, was the subject of a lot of criticism despite the fact that this was far from the first time that Penn had interviewed a controversial person. Still, when you consider the fact that Penn was willing to sit down and speak with someone who has claimed responsibility for thousands of deaths truly shows how out of whack Pennā€™s sense of morality truly is.

  • He Declared That American Journalists Should Be Arrested For Lying

    He Declared That American Journalists Should Be Arrested For Lying
    Photo: YouTube

    One person that Penn had a positive relationship with was the former Venezuelan president Hugo Chavez. Chavez was criticized heavily during his two-decade presidency for being a socialist dictator, and while opinions of Chavez vary, Penn was very clear about his support and admiration for the man. In 2010, Penn said, ā€œEvery day this elected leader is called a dictator here, and we just accept it, and accept it. And this is mainstream media. There should be a bar by which one goes to prison for these kinds of lies." Thatā€™s right, Penn called for the imprisonment of American journalists for criticizing a foreign leader.

  • He Freaked Out When Charlize Theron Dumped Him After Starring In His Film

    He Freaked Out When Charlize Theron Dumped Him After Starring In His Film
    Photo: YouTube

    In 2016, Charlize Theron and Sean Penn made news at the Cannes Film Festival after they noticeably kept a distance from one another despite the fact that they were both promoting The Last Face and had been dating a year earlier when the film went into production. While Theron has been tightlipped about what lead her to ghost him, sources close to the couple explained that ā€œCharlize refuses to tell anyone the specifics, but they had a fight that left her completely shaken... Sean later blamed alcohol and begged her not to leave him.ā€ Given his past, this explanation seems to check out.

  • His Son Proved That The Apple Doesnā€™t Fall Far From The Tree

    His Son Proved That The Apple Doesnā€™t Fall Far From The Tree
    Video: YouTube

    In 2013, Pennā€™s son Hopper proved that parents' actions really can rub off on their kids. During an outing with his good ol' dad, Hopper dealt with a paparazzi in true Sean Penn 1980s style. As the camera was rolling, Hopper pushed the photographer and began cussing him out, saying, "F*ck you...you're a f*cking f*ggot...shut up you f*cking n*****." The photographer did not press charges, and Hopper publicly apologized saying, "I deeply regret my choice of words,ā€ but not before he slightly defended his response, saying, ā€œI was accosted by paparazzi and made to feel like an animal - threatened and under attack.ā€ Sounds familiar.