Resurfaced Clip of Sean Penn Talking About Madonna Marriage: ‘I’ve Never Met the Woman’
The actor's cheeky response on Letterman about his famous ex has fans buzzing decades later
A decades-old clip of Sean Penn making a cheeky joke about his marriage to Madonna has everyone talking all over again. In a 1995 appearance on Late Show with David Letterman, when the host asked about his famous ex-wife, Penn delivered a response that was equal parts witty and savage: ‘I’ve gone on record with you before, I’ve never met the woman.”
The Oscar winner, known for roles in Milk (2008) and Mystic River (2003), has had several high-profile relationships over the years, including his most recent relationship with actress Leila George and before that, screen icon Robin Wright. But it was his first marriage to the pop icon that really captured public attention—and apparently still makes for great late-night TV fodder decades later.
“We haven’t had a chance to chat since your ex-wife was here, Madonna,” remarked Letterman. “She was here about, I don’t know, a year and a half ago or something—and talk about all hell breaking loose. It was a crazy night,” the talk show host joked. “ Do you have a relationship with the woman now? Are you friends?” Thinking about his answer, Penn responded with a clever, “I’ve gone on record with you before, I’ve never met the woman.”
“Since that one evening, I’ve kind of gotten to know her a little bit better and I have a completely different impression of her. I think she’s a very nice, very smart young woman,” said Letterman, to which Penn replied, “I’m sure she is.” While their exchange could have been nothing more than playful back and forth, both Penn and Madonna have opened up about their past together in a positive light in recent years, claiming to maintain a close relationship.
Madonna and Sean Penn relationship
It was love at first sight when the two met on the set of Madonna’s “Material Girl” music video in 1985. Just six months later, they were husband and wife. But the whirlwind romance couldn’t withstand the pressures of two mega-careers in the spotlight, and they divorced in 1989 after four years together. In the time they were together, they appeared in the film Shanghai Surprise (1986). The two didn’t have any children together, but they remained friends over the years, speaking fondly about one another.
Back in 1991, in the documentary of Madonna’s life, Truth or Dare, the singer claimed that Penn was the love of her life. And in the 2025 documentary film Becoming Madonna, the director of the “Material Girl” music video, Sharon Oreck, stated that “She was genuinely in love with him, but it felt as if the attraction between the two of them was fueled by the public,” as reported by People. “He was the budding movie star, she was the budding rock star and the public demanded that they come together.”
Earlier this year, on The Louis Theroux Podcast, Penn reacted to Madonna’s 1991 commentary on their relationship. “Look, she’s been a good friend for a lot of years,” he said. “It didn’t take us long to realize that we had mistaken a good first date for a wedding partner,” the actor continued. “It didn’t take us long to recover after we got divorced, maybe a year, in a friendship. I have a lot of fond memories of it—it’s not all jail.”
The fact that both stars can look back on their relationship with humor and fondness shows that sometimes the greatest love stories aren’t the ones that last forever, but the ones that teach us about ourselves and leave us with cherished memories and lifelong friendship.
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