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Sean Penn reveals what really happened with arrest involving Madonna and paparazzi


The One Battle After Another actor was married to the "Like a Virgin" singer from 1985-89, and was involved in legal issues involving paparazzi multiple times


Sean Penn attends the "One Battle After Another" London Premiere at Odeon Luxe Leicester Square on September 16, 2025 in London, England© Getty Images
Ahad Sanwari
Ahad SanwariSenior Writer - New York
Updated: 3 days ago
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Sean Penn may be considered one of the industry's most respected and outspoken actors now, but back in the 1980s, soon after making his film debut, he was also considered one of its troublemakers. While earning major credit for films like Fast Times at Ridgemont High and At Close Range, he was also involved in a very highly-publicized relationship with Madonna, who he was married to from 1985 to 1989, plus a string of legal issues during that decade often involving the paparazzi.

The actor, now 65, who stars in the new acclaimed Paul Thomas Anderson film One Battle After Another, spoke with the New York Times about some of his troubles then as part of their "The Interview" series, specifically honing in on an incident in 1986, when he allegedly dangled a photographer off a hotel balcony in Macau, where he was staying with Madonna.

Further referenced in his biography Sean Penn: His Life and Times, Sean was asked about whether he'd apparently broken out of jail after being charged over the incident and "escaped" the country via a jetfoil. At first, he simply quipped: "It's like the ferry. They go back and forth all day," before diving into the whole situation further.

"We were passengers on the jetfoil," the two-time Oscar winner continued. "We got on like normal passengers and then had to go to a house on the Kowloon side and wait until something got settled," and then went on to explain whether he did actually dangle the photographer over a hotel balcony, believed to be a correspondent for the Hong Kong Standard

Sean Penn attends the World Premiere of Warner Bros. "One Battle After Another" at TCL Chinese Theatre on September 08, 2025 in Hollywood, California© Getty Images
Sean Penn looked back on his life and career, specifically even honing in on an incident in 1986

"But the guy, first of all, we didn't put him past his waistline over that balcony. There was never an intent to drop him off of it," Sean detailed. "My friend at the time, who was my kickboxing trainer, needed a job, so I got him a job as security. He overreacted. This guy was holding something when he jumped out at us, and my friend responded instinctively; I responded instinctively." 

Musician Madonna and actor Sean Penn attend the 5th Annual Sean Penn & Friends HELP HAITI HOME Gala benefiting J/P Haitian Relief Organization at Montage Hotel on January 9, 2016 in Beverly Hills, California.© Getty Images
The actor was married to Madonna from 1985-89, although they remain friends to this day

"About halfway to the balcony, I saw it was a camera and not a weapon. So I was marching him through the room, also through what was an open balcony, and yeah, we got him down across it and I'm yelling at my friend, 'It's a camera,' and we didn't have time to pull him back before the hotel security turned on us and grabbed us."

Actor Sean Penn and singer Madonna leave the Mitzi E Newhouse at Lincoln Center, New York, New York, August 13, 1986. They were on a break during rehearsals for the Lincoln Center Workshop's production of 'Goose and Tomtom.'© Getty Images
The couple were often followed by the paparazzi, and their turbulent relationship was highly publicized

He joked: "We never got to show we weren't gonna kill him, and that's when 'Midnight Express' happens and we just blew out of there and ran to the jetfoil, and that's the whole story," clarifying that there wasn't any "James Bond" element to the story. Sean channels that anger into his current role in One Battle After Another as well, playing Colonel Steven J. Lockjaw.

"We never got to show we weren't gonna kill him, and that's when 'Midnight Express' happens and we just blew out of there and ran to the jetfoil."© Getty Images
"We never got to show we weren't gonna kill him, and that's when 'Midnight Express' happens and we just blew out of there and ran to the jetfoil."

The film revolves around Bob Ferguson (Leonardo DiCaprio), a father and ex-revolutionary struggling to protect his daughter Willa (Chase Infinity) from Colonel Lockjaw, who is hell bent on wiping out revolutionary and racial idealism. Other characters include Willa's mother Perfidia (Teyana Taylor), and some of Bob's accomplices, sensei Sergio (Benicio del Toro) and Deandra (Regina Hall).

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