The Secret Illegal Life Of Sean Penn

Actor Sean Penn loves giving the impression that he's a peaceful humanitarian and diplomat. He leads the Help Haiti Home organization and befriended former Venezuelan president Hugo Chavez, but the two-time Oscar winner's actions also suggest he can be a potentially violent outlaw. Let's examine Penn's often overlooked criminal side.

That time he assaulted some photographers

In July 1985, Penn was arrested after he allegedly attacked two freelance journalists with a rock for having the nerve to try taking a picture of him and then-fiancée Madonna. "He went for us like a madman," reporter Ian Markham-Smith told the Los Angeles Times. "He just went for us straight off. He went berserk, like a whirlwind." He pleaded no contest to the charges, served a suspended sentence, and paid $50 in fines, according to the Associated Press.

That time he punched a guy for talking to Madonna

Penn allegedly punched a songwriter named David James Wolinski in a nightclub in April 1986 because he thought the man was kissing Madonna. (People reports that Wolinski was simply saying goodbye to Penn's then-wife.) Penn hit Wolinski so hard and so many times that Wolinski was knocked out of his seat. Penn was fined $1,700 and given one year of probation.

That time he was accused of attempted murder

Penn was also accused of attempted murder in 1986. In the biography Sean Penn: His Life and Times (via The Sydney Morning Herald), author Richard Kelly claims Penn dangled a photographer off his 9th floor balcony in Macau (then a Portuguese colony) while filming Shanghai Surprise (1986). Penn was reportedly arrested and jailed, with his assistant in tow, but the pair escaped when their cell door was left open. They hopped on a flight to Hong Kong, and Penn was eventually pardoned by Portuguese authorities.

That time he assaulted an extra and failed a sobriety test

In June 1987, Penn was sentenced to 60 days in jail and two years of probation for two separate offenses. The Los Angeles Times reports that Penn punched and spit on an extra on the set of Colors (1988) for allegedly photographing him and co-star Robert Duvall. The extra had to be hospitalized for his injuries. Penn had also been pulled over days before under suspicion of drunk driving after he sped through a red light. Penn reportedly failed field sobriety tests, but pleaded his DUI down to reckless driving.

That time he may or may not have beat up Madonna

Penn was also accused of assaulting Madonna in 1987. The Daily Mail reports, "In June 1987, Madonna went to the Cedars Sinai hospital [in Los Angeles] for an X-ray after Penn apparently hit her across the head with a baseball bat." Penn was rumored to have bound and gagged the queen of pop, who was rendered "unrecognizable" from the alleged beating.

There isn't much evidence to corroborate the claim, though Gawker compiled a slew of articles and sources indicating that the horrific episode did, in fact, go down. Penn and Madonna would later fiercely deny the allegations (even though Madge was cagey when asked if she filed an incident report about it), and Penn even filed a $10 million lawsuit against Empire creator Lee Daniels for defamation of character for having the nerve to bring it up.

Still, Penn admitted to Playboy in 1991 that authorities were, in fact, called to the residence. "A SWAT team surrounded my house and came in every door. But it happened because on the day that we split up, she developed a concern that if she were to return to the house, she would get a very severe haircut....So she took this concern to the local authorities, who came back up to the house. She felt the responsible thing to do would be to inform them—since they were coming up there ostensibly to keep her from getting a haircut and to let her gather some personal effects—that there were firearms in the house." Even then, Penn was quick to add, "No charges were ever filed."

That other time he attacked a photographer

In October 2009, a photographer filed a police report against Penn after the actor was caught on camera kicking and hitting him multiple times and breaking his camera in the process. TMZ reported that Penn was charged with misdemeanor vandalism and misdemeanor battery for the violent tantrum, which left the paparazzo needing surgery for his injuries. Penn faced up to a year and a half in jail for the offenses, but pled down to 36 months of probation, 300 hours of community service, and 36 hours of anger management classes.

That time he met with an international drug kingpin

Penn's Rolling Stone article on infamous Mexican drug lord Joaquín Archivaldo Guzmán Loera (aka El Chapo) was portrayed by the magazine as a glorious journalistic endeavor, but Penn may face charges for the meeting with the escaped king pin.

A Fox News report suggests Penn may have been gunning to play El Chapo in a movie and met with him to master the role...under the guise of a story for the magazine. If he was there purely for the story, it's all kosher under freedom of the press, but if evidence of any other motive comes out, Penn could be in big trouble.

"Sean Penn seems to be bending over backward to say it was purely journalistic, but the info we were given about the trip, there was never any reference to an interview for a Rolling Stone article until he met with El Chapo," a government source told Fox News. "I think this was a very calculated move on the part of Sean Penn based on legal counsel to try and hide behind the freedom of the press and the First Amendment to avoid prosecution." The insider explains, "Meeting with El Chapo about making a movie about him would have been violating U.S. law, which prohibits dealings with a 'significant foreign narcotics trafficker.' Penn said his story was a 'failure' because the real objective was to ignite the debate on how the war on drugs is a failure, but it is not a failure if he lands in the role of a lifetime."