Jordan Karlesson
After three decades and two divorce filings, it appears Madonna and Sean Penn will always share a romantic connection.
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The Material Girl’s marriage to Penn lasted less than four years and ended with litigation. But love can transcend courtroom disputes.
Madonna called Penn the love of her life in her 1991 documentary In Bed with Madonna, as U.K. tabloid The Sun notes. Almost 25 years later, she still seemed to be his (possibly) when he showed up at two of her concerts.
But in 2022, even though neither celebrity is currently married, the chances of seeing them tie the knot again are slim to none. Their messy divorce is likely to blame for that.
Madonna and Sean Penn: Mad About — and at — Each Other
Madonna and Sean Penn’s tumultuous relationship is still the stuff of legend. Few marriages equaled theirs in terms of tabloid attention, especially in the pre-TMZ era.
They married in August 1985, when Madonna was 27 and Penn was 25.
“We have so much in common that he’s almost like my brother,” Madonna said before the wedding, People reported. “His temperament is also similar to mine. That doesn’t always make for ideal relationships, but I don’t know what will happen.”
But as dreamy as starry-eyed Madonna considered Penn, their split was nightmarish.
People featured its report in a December 1987 issue, the cover of which had a photo of Madonna and Sean Penn along with the title Diary of a Mad Marriage.
“Jealousy, booze and brawling sink Hollywood’s most outrageous couple,” People breathlessly reported.
In particular, Madonna and Sean Penn’s dramatic relationship played out in public thanks to their starring turns in the flop Shanghai Surprise. As reported by 20th Century Danny Boy, a blog covering the entertainment industry, their fights became a distraction from shooting the movie.
“Sadly the production was dogged by problems, rumors and innuendo, with reports of fights,” the blog said. “Penn giving orders to the director, Madonna being petulant, theft of property and more. The more work that was done, the more intense the media scrutiny and more problems became apparent.”
The Divorce and the Aftermath
They divorced in 1989 but, surprisingly, kept supporting each other’s careers in the subsequent decades.
Perhaps most poignantly, Penn popped up at two Madonna concerts in 2015. A few years later, he said on The Late Show with Stephen Colbert that he still loved Madonna “I love my first wife very much. … I’m a Madonna guy.”
For her own part, Madonna commented on Penn showing up at the shows.
“I did a show at Madison Square Garden the other night if you heard about it. And my ex-husband was there! Could you imagine?” Madonna told the crowd, according to Us Weekly.
“He had been at my show 30 years earlier when I was at Madison Square Garden, and he was very upset with me for wearing a costume that was too revealing. That’s not a lie!” she reportedly said about Penn. “Anyway, after the show he wrote me a letter and said he finally appreciates my art. And that is what I have to say about marriage, okay!? Thirty f–king years later.”
And that pretty much sums it all up.
