Sean Penn is no stranger to drama, both on and off the screen.
In addition to his career as an Oscar-winning actor and his relationships with A-listers including Madonna, Robin Wright and Charlize Theron, Penn has made headlines through the years for controversial behavior and comments.
Keep scrolling to for a look back at Penn’s biggest controversies over the years:
Alleged Abuse of Madonna
Penn was married to the “Queen of Pop” from 1985 to 1989. Madonna first filed for divorce in December 1987 but withdrew the papers two weeks later. In January 1989, she filed for divorce again.
Reports surfaced in 1987 — and again in 1989 — alleging that Penn had physically assaulted Madonna. The musician later shut down the claims in 2015 when she testified on Penn’s behalf amid his defamation lawsuit against director and screenwriter Lee Daniels.
According to court documents obtained by The Hollywood Reporter, Madonna’s statement denied reports that Penn allegedly struck her with a baseball bat in 1987 and physically assaulted her in 1989.
“While we certainly had more than one heated argument during our marriage, Sean has never struck me, ‘tied me up,’ or physically assaulted me, and any report to the contrary is completely outrageous, malicious, reckless, and false,’” Madonna’s statement read.
After Penn’s divorce from Madonna, he was later married to Wright from 1996 to 2010 and to Leila George from 2020 to 2022. He and Wright share daughter Dylan, born in 1991, and son Hopper, born in 1993.
Incident With David Wolinski
In 1986, Penn was charged with misdemeanor battery for allegedly assaulting Wolinski, a songwriter best known for his work with the band Rufus, at Helena’s nightclub in Los Angeles. Wolinski claimed that the incident began when Penn accused him of trying to kiss Madonna.
Penn pleaded not guilty to the charge and was sentenced to one year of probation.
Stint in Jail
In 1987, Penn was arrested for punching Jeffrey Klein, an extra on the set of his film Colors. Penn was already on probation at the time and was sentenced to 60 days in jail for the assault and for reckless driving. He served 33 days of the 60-day sentence.
Altercation With Photographer
In May 2010, the actor pleaded no contest to a misdemeanor charge stemming from an October 2009 altercation with photographer Frank Mateljan. He was sentenced to perform 300 hours of community service and to undergo 36 hours of anger management counseling.
Footage of the incident obtained by TMZ showed Penn kicking toward the photographer. “Get out, get out,” Penn said as he kicked.
Lawsuit Against Lee Daniels
Daniels mentioned Penn during a September 2015 interview with The Hollywood Reporter when asked about Terrence Howard’s continued career in show business despite his ex-wife Michelle Ghent obtaining two restraining orders against him for alleged domestic abuse in 2011 and 2013.
“[Terrence] ain’t done nothing different than Marlon Brando or Sean Penn, and all of a sudden he’s some f—king demon,” Daniels claimed during the interview.
In response, Penn sued Daniels for defamation, seeking $10 million in damages. He dropped the lawsuit in May 2016 after Daniels issued a public apology retracting his statement.
“I am so sorry that I have hurt you, Sean, and I apologize and retract my reckless statements about you. How thoughtless of me. You are someone I consider a friend, a brilliant actor and true Hollywood legend and humanitarian,” Daniels’ statement began.
Daniels also called his previous remarks about Penn “cavalier” and said he made them to “express a view regarding the disparate treatment of men of color in our national conversation.”
Comments About Masculinity
Penn raised eyebrows for comments he made about masculinity during a January 2022 interview with the British newspaper i.
“I am in the club that believes that men in American culture have become wildly feminized,” he told the outlet at the time. “I don’t think that being a brute or having insensitivity or disrespect for women is anything to do with masculinity, or ever did. But I don’t think that [in order] to be fair to women, we should become them.”
Later that month, he doubled down on his remarks while speaking with the Independent.
“I think that men have, in my view, become quite feminized. I have these very strong women in my life who do not take masculinity as a sign of oppression toward them,” he said. “There are a lot of, I think, cowardly genes that lead to people surrendering their jeans and putting on a skirt.”
Actress Thandiwe Newton was among those who took issue with Penn’s statements.
“Dude what are you saying?” she wrote via Twitter in response to the Independent interview. “Like for real? You’re a jibbering fool … you used to be sexy but now you’re just tragic.”
Comments About Will Smith
“I don’t know Will Smith. I met him once. He seemed very nice when I met him. He was so f—king good in King Richard,” Penn said during a September 2023 interview with Variety.
He continued, referencing the jail time he served for punching Klein in 1987: “So, why the f—k did you just spit on yourself and everybody else with this stupid f—king thing? Why did I go to f—king jail for what you just did? And you’re still sitting there? Why are you guys standing and applauding his worst moment as a person?”