Madonna's Confessions II drops tomorrow, and from what's been released so far, it's clear she's not holding back musically or lyrically. She has a track titled "Bizarre," and all signs point to it being about her ex-husband, Sean Penn.
© Barry KingFor decades, Madonna and Penn's relationship has made headlines. It was explosive, emotionally charged, and layered. Nearly 40 years later, the Queen of Pop sings about a movie star with “deep blue eyes,” a man seemingly threatened by her power and fame.
She never says Penn’s name, but the clues are all there, including a specific reference to a Shelby Cobra. Madonna was famously rumored to have gifted Penn a Shelby when they married in 1985, making the lyric “He drove way too fast / Shelby Cobra, wasn’t meant to last” hold a lot of weight.
Their relationship has always been a part of Hollywood folklore. When they married in 1985, they were cultural symbols colliding.
© GettyYears later, she still describes the intensity. “The little things that you did that madе me want you / The fire was so intеnse," she sings.
Madonna and Penn met on the set of her “Material Girl” music video and were married just six months later, on August 16, 1985. It was Madonna’s 27th birthday and the day before Penn turned 25.
Even their wedding felt chaotic from the start. Helicopters swarmed overhead as paparazzi tried to capture every second, creating so much noise that Madonna later admitted she could barely hear the vows.
In the documentary Becoming Madonna, Sharon Oreck, who worked on her iconic “Material Girl” video, described Penn as America’s bad boy and Madonna as America’s bad girl.
© Ron Galella, Ltd.“She was genuinely in love with him, but it felt as if the attraction between the two of them was fueled by the public," she explained. "He was the budding movie star; she was the budding rock star, and the public demanded that they come together.”
The cracks in their marriage became public in December 1987, when Madonna filed for divorce after just over two years of marriage.
She briefly withdrew the filing less than two weeks later, but by January 1989, the split became permanent, marking the end of one of Hollywood’s most volatile unions.
Her reps told PEOPLE at the time, "There was no one direct incident leading up to this. "It was a series of cumulative pressures. There were many moments in their marriage when it was shaky, and Madonna was finally forced to face the reality of the situation — that they weren't happy together."
But despite the turbulence, neither has ever fully erased the other. In her 1991 documentary Truth or Dare, Madonna famously called Penn the love of her life.
In 2025, while on The Louis Theroux Podcast, Penn talked about her admission, calling her “a good friend for a lot of years” and admitting they had “mistaken a good first date for a wedding partner.” “It didn’t take us long to recover after we got divorced, maybe a year, in a friendship," he said, "I have a lot of fond memories of it – it’s not all jail.”
© L. CohenAnd she had his back in 2015, swearing in court that he never physically assaulted her. Madonna said, “While we certainly had more than one heated argument… Sean has never struck me, ‘tied me up,’ or physically assaulted me.” At the time, Lee Daniels had publicly called Sean Penn a “wife beater,” prompting Penn to sue him for defamation. The case was later settled, and Daniels apologized.
Their 2016 reunion
They sparked reconciliation rumors when they were spotted holding hands at the Help Haiti Home gala in 2016, and later made headlines in December 2016 when she hosted a charity gala at Art Basel in Miami.
© GettyPenn was in the audience, and the auction included three black and white photos from their wedding. She told Penn, "I'm still in love with you," and offered to remarry him if he bid $150,000.
While they didn't remarry, he did join her on stage and crawl through her legs to encourage people to bid higher. She ended up raising more than $7.5 million for the African nation of Malawi, per Associated Press.
Who are they dating now?
© GettyMadonna married filmmaker Guy Ritchie in 2000, and they divorced in 2008. She's been locked in with her boyfriend, Akeem Morris, since 2024.
© Arnold JerockiAs for Penn, he went on to marry actress Robin Wright from 1996- 2010, then Leila George from 2020–2022. He's been dating 30-year-old model and actress Valeria Nicov since September 2024.
