Sean Penn is known for being a brilliant actor, but is he talented enough for both the public and his colleagues to ignore his pattern of violent and eyebrow-raising behavior? Apparently the answer to this question is yes, because Penn’s numerous arrests and other counts of strange conduct have flown under the radar for years. Here’s a timeline of the actor’s questionable background.
1985: Assault
In 1985, at the age of 24, Penn was arrested for allegedly attacking two freelance journalists with a rock, according to the Los Angeles Times. “He went for us like a madman,” one of the journalists said. “He went berserk, like a whirlwind.”
1986: Attempted murder
Penn was charged with attempted murder for dangling a paparazzi photographer over the side of a 9th-floor hotel balcony on the Chinese island of Macao, according to AskMen. He later told a biographer that he was taken to jail, but escaped through an ajar door and fled the colony.
1986: Assault
The same year Penn escaped from jail, he was arrested stateside for hitting a man he accused of trying to kiss his wife. He pleaded guilty and was placed on parole.
1987: Assault
Penn served 30 days in jail for violating his parole by punching an extra on the set of his film Colors because he tried to take a photo of him.
1987: Felony assault
Penn found himself in trouble again and was arrested for felony domestic assault after reportedly beating his then-wife, Madonna, for nine hours. Penn tied Madonna to a chair, hit her across the head with a baseball bat and threatened to shave her head.
1998: Assault
Penn was accused of attacking — you guessed it — a photographer with a rock again, but he denied it and said that the photographer attacked the rock that was in Penn’s hand and injured himself. No arrest was made.
2008: Cheating rumors
After Penn and then-wife Robin Wright separated, reports that their divorce was caused by Penn’s love of Russian hookers began to surface.
2009: Assault
Penn was caught on camera assaulting yet another photographer, a crime for which he got 36 months’ probation, 300 hours of community service and was ordered to pay a sizable settlement to his victim, according to TMZ.
2010: Politics
Penn came under criticism after he backed Venezuelan president Hugo Chavez, a figure widely known to be a socialist-near-autocrat accused of driving the Venezuelan economy into the ground.
2010: Slams Britain
Members of British parliament called Penn “moronic” after the actor said sending Prince William to the Falkland Islands is an act of “colonialism” at its worst.
2011: Name calling
When actress Maria Conchita Alonso, a native Venezuelan, calmly confronted Penn about his politics involving her home country, Penn allegedly refused to speak to her and called her a pig.
2013: Verbal with fan
Penn was caught on a TMZ camera screaming at a fan who tried to take a picture of him outside of a San Francisco Hotel. “I’ll make you eat the phone… Get the f*** out of here. Get out of here!” Penn yelled before throwing the man’s phone to the ground.
2014: Alleged abuse
Police were called on Penn and his fiancée, Charlize Theron, by a hiker who said she was concerned for the safety of Theron’s son, who appeared to be extremely upset while the trio was picnicking in a public park. Police deemed the boy to be fine and no arrests were made.
2015: Racist joke
Penn offended more than a few people when he said “Who gave this son of a bitch his green card?” in reference to Mexican-born director Alejandro González Iñárritu, causing Twitter to light up with reminders of all of Penn’s past transgressions.
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