Do You Remember: The Paparazzi Invasion of Madonna and Sean Penn’s Wedding

CONTENT WARNING: This piece discusses domestic violence and abuse against women.

The upcoming release and promotional rollout for Confessions 2 has this Madonna fan in a tizzy. Longtime readers of my work will know that I love Madonna. I was so determined to see her greatest hits tour in 2023 that I flew out to Copenhagen to make it happen. No other star aside from Elizabeth Taylor has done more to shape my fascination with celebrity studies and the narratives they, the media, and their fans craft around them. Madonna is the queen of reinvention, after all, a woman who, for a period, was arguably the most famous person alive. Now in her imperial era, Madonna largely surrounds herself with gorgeous boytoys and brags about how great John F. Kennedy Jr. was in bed (I buy it.) 41 years ago, she tied the knot under a sea of helicopters, further cementing her status as an idol. Her husband at the time was less thrilled.

In late 1984, Madonna was filming the music video for the song "Material Girl." Forever a cinephile, she used the video as a chance to flex her status as a star, recreating the "Diamonds Are a Girl's Best Friend" scene from Gentlemen Prefer Blondes with herself in the Marilyn Monroe role. During the shoot, she met Sean Penn, a rising star from an acting family who was earning a reputation as an intense performer. He was probably best known at the time for his turn as the stoner Spicoli in Fast Times at Ridgemont High, but Penn fancied himself to be the next James Dean or Dennis Hopper, and he took himself extremely seriously. When he met Madonna, he thought it was kind of arrogant of her to dress like Marilyn, but he also liked her, so he basically negged her. Madonna chewed him out for his rudeness, but he was also the exact kind of guy she had a soft spot for.

They were both young (she was 2 years older than him), on the rise in their respective careers, and the chemistry was undeniable. Together, they became even more famous, almost as symbols of '80s-era stardom. She was the self-aware and nakedly ambitious pop queen, and he was a son of Brando, a man who thought acting was a life-or-death matter. She loved the attention and knew how to wield it. Penn basically wanted every photographer who crossed his path to die in a fire.

It was something of a whirlwind romance, and the pair were quickly engaged. Penn asked Madonna to keep it secret, which she sort of did. She only told her Desperately Seeking Susan co-star Rosanne Arquette the happy news. And then she told someone. And they told someone. Then everyone in Hollywood knew, and so did the press. They had always been aggressive in their pursuit of the pair, and this only exacerbated things.

In June 1985, Penn and Madonna were in Nashville while Sean worked on the film At Close Range. Two freelance photographers working for the British Murdoch-owned tabloid The Sun were camping outside the hotel the pair were staring at, hoping for a few good shots. “We wanted to find out if we could get Sean Penn and Madonna quotes about their forthcoming marriage and, if possible, get a picture of them together,” said Lawrence Cottrell to The Los Angeles Times. “We hadn’t taken a picture, but Penn spotted us and figured out who we were.” The journalists said they approached the couple when Madonna returned from jogging, but Penn grabbed a rock and threatened the men, yelling, "No pictures—you take my picture and I’ll break your back with this rock." He then threw the rock and hit one of them in the back. Penn was arrested and later pleaded no contest to assault charges. This wouldn’t be the first time he’d face legal trouble relating to his paparazzi rage. It probably just made the press’s hunger for access to the upcoming Penn wedding even worse.

The date and location of the big day were meant to be a secret kept among the pair’s closest family and friends. The plan was for it to be a surprise, with guests thinking they were there for a joint birthday party (their birthdays are one day apart.) But as with the engagement itself, people soon discovered the truth. The location was Point Dume, Malibu. Dan Unger, a friend and property tycoon, had given the pair use of his home for the ceremony and party. Guards were throughout the location, checking IDs and weeding out intruders. They found an Italian photographer in full camo gear hiding in the shrubbery thanks to some infrared binoculars.

The guest list included Tom Cruise, a purple-haired Cher, and Christopher Walken. Keith Haring, a longtime friend of Madonna's, was also there. So was Andy Warhol. Debi Mazer, her other BFF, wore a green and black two-piece top and skirt with a matching bandana. Photographers waited outside to snap photos of the guests, but couldn’t get into the compound itself.

But there are these things called helicopters.

They got so close to the building that it drowned out the couple's vows and threatened to blow away Madonna's veil and black bowler hat. The copters and paparazzi, which included the famous Zoey Tur, got a lot of juicy shots, including one of Sean with his head under Madonna’s skirt trying to remove her garter, and one of the bride flipping them the bird. On the beach beneath the cliffs, the words “FUCK OFF” were spelt out on the sand.

These were large airborne vehicles that were loud, aggressive, and tough to control, and several of them were fighting for airspace to get footage of a singer marrying an actor. Celebrity weddings have always attracted outsized attention. The rumoured Madison Square Garden nuptials of Taylor and Travis are recent proof of that. It's no surprise why People or Vanity Fair or CNN (?) would be so desperate for photographs of a party full of famous people cutting loose, but it must have been a surreal moment for the couple. Imagine having to organise your wedding with the privacy of a military operation and having it conclude with a scene right out of Apocalypse Now. To add to the carnage, Penn opened fire on the copters with a handgun.

Andy Warhol called it “the most exciting weekend of my life.”

Famously, the Ciccone-Penn marriage was a volatile one. Sean got jealous easily. He couldn’t handle Madonna’s fame or courting of attention, and he hated hearing about her past partners. She dedicated her album True Blue to him, and they made a truly awful film together, Shanghai Surprise. Penn kept attacking photographers. In January 1986, he was arrested for assaulting a man while in Macau. Five months later, he was charged with misdemeanour battery for assaulting songwriter David Wolinski, who he accused of trying to kiss Madonna. In 1987, he violated his probation by punching an extra on the set of the film Colors and served 33 days of prison time. Penn claims he was in the same jail as Richard Ramirez, the Night Stalker.

Madonna filed for divorce from Penn on December 4, 1987, though she later withdrew the petition. She filed again in January 1989. That month, she had an assault report with the Sheriff's Department of Malibu over an incident in their home over the New Year. The contents of that report were never disclosed, but a British tabloid claimed that Madonna was beaten, gagged and left strapped to an armchair for nine hours. Columnist Liz Smith also reported the alleged incident, saying Madonna was ″trussed up like a turkey.″ Madonna later withdrew her report.

It’s tough to talk about this incident because so many versions of the story have floated around for decades, and because both Penn and Madonna have said she was never physically abused. A lot of articles that talk about it are no longer online. An unauthorised biography from 1991, published only in the UK at that time, claims that Penn beat her and sexually assaulted her. That book quotes from Lieutenant Bill McSweeney, one of the Malibu sheriffs who witnessed Madonna approach the station to file her report. He would usually be bound by privacy laws, but in the book, he’s quoted as saying, “It was a unique, specific type of violence […] It was a serious matter. It was something that if prosecuted would have had great implications.”

It is true that law enforcement was summoned to their home. Penn told Playboy in 1991 that it was because Madonna “developed a concern that if she were to return to the house, she would get a very severe haircut.” He had threatened to cut off her hair during an argument. Penn claimed the tabloids made up the story, but he also confirmed that at least a couple of parts, like the haircut threat, were true. In July 2001, another unauthorised biography of Madonna, this one by J. Randy Taraborrelli, claimed to have obtained the police report from that evening. It, they claimed, detailed how Penn had “tried to bind her hands with an electric lamp and cord.” She tried to flee, and Penn allegedly managed to tie her to an easy chair with twine. “As per the police report, Penn was ‘drinking liquor straight from the bottle,’ and his abuse of her went on for several hours, during which time he allegedly smacked her and roughed her up.” The book also quotes Lt. McSweeney as saying, “I hardly recognized her as Madonna, the singer. She was weeping, her lip was bleeding and she was all marked up. This was a woman in big trouble, no doubt about it.”

In 2015, Penn sued director Lee Daniels for libel after he used Penn as an example of double standards in America regarding accusations of violence against women. While defending Terrence Howard, who has been repeatedly accused of assaulting women, Daniels said, “[Terrence] ain’t done nothing different than Marlon Brando or Sean Penn, and all of a sudden he’s some fuckin’ demon. That’s a sign of the time, of race, of where we are right now in America.” Penn’s lawyer would tell Gawker, “As both Sean Penn and Madonna indicated on the public record more than 25 years ago, the notion that Mr. Penn ‘struck’, ‘tied up,’ or ‘beat up’ Madonna is false, outrageous, malicious, and defamatory.” 

There’s an extremely thorough article from Gawker that gives a detailed timeline of the abuse allegations. It offers an intriguing insight into how Penn has responded to these claims in some pretty careful language, and how this story has evolved in the ensuing decades. When I first heard the story, it involved Penn beating Madonna with a baseball bat, but as Gawker notes, there’s zero mention of a bat from the reporting of this time. Yet it is now part of the myth.

Madonna herself has spoken out in support of Penn many times over the years following their divorce. She has never lost her fondness for her first husband and has appeared alongside him at several events. In 2015, while Penn was suing Daniels, she signed a sworn affidavit that declared, “Sean has never struck me, ‘tied me up,’ or physically assaulted me, and any report to the contrary is malicious, reckless, and false.” Penn dropped the lawsuit in May 2016 after Daniels retracted his statement and issued an apology.

Sean Penn has more than proven himself to be a dick. He’s gotten into enough on-camera fights and demonstrated his unbearable ego with frequency during his long and storied career. The man has unresolved issues he’s never felt the need to fix because three Academy Awards and a slew of young girlfriends mean he’ll never have to. They are the only people who will never know what happened between him and Madonna, and the stories told about their marriage stuck around for a long time because… well, because the image of Madonna tied to a chair by her husband was too potent to ignore.

They never entirely made sense as a couple, but every article I’ve read from people who knew them said their love was real, intense, and kind of overwhelming to be around. Her affidavit probably didn’t quash every person’s theories about that arrest. The Gawker piece showed why the story stuck around, thanks to just enough ambiguity around Penn’s statements to add fuel to the fire. If she says he never beat her, we have no reason to deride or deny her experiences. Regardless, the Penn marriage was and remains a topic of endless media fascination.

Dancer: Madonna, truth or dare?

Madonna: Truth.

Dancer: Who has been the love of your life?

Madonna: My whole life? Sean. Sean. (Madonna: Truth of Dare.)