Madonna, now 66, and Penn, 64, first met on the set of her iconic "Material Girl" music video in February 1985. Sharon Oreck, the producer of the video, revealed in archival audio featured in the documentary that Madonna was "genuinely in love" with Penn. However, Oreck noted that their relationship was fueled, in part, by public fascination. "He was the budding movie star, she was the budding rock star, and the public demanded that they come together," Oreck said.
The couple married just six months later on Madonna’s 27th birthday, August 16, 1985, which also marked the eve of Penn’s 25th birthday. The ceremony in Malibu, California, drew massive media attention, with helicopters hovering overhead. Madonna later admitted in the documentary that she “couldn’t hear the vows” due to the noise. Her brother, Christopher Ciccone, shared that the intrusion frustrated Penn, who reportedly wrote an expletive in the sand for the helicopters to capture.
Ciccone, who passed away in October 2024 at age 63, reflected on the chaotic wedding day, calling it a "bad omen" for their future. The marriage faced significant challenges, including frequent media scrutiny and personal conflicts.
By December 1987, Madonna filed for divorce, citing "cumulative pressures" and acknowledging that the marriage was not making them happy. Although she briefly withdrew the filing, she finalized the divorce in January 1989.
Despite their turbulent past, Madonna and Penn have remained on good terms. In 2016, Madonna publicly declared she was "still in love" with Penn during a charity gala, even jokingly offering to remarry him if he placed a $150,000 bid. The event raised over $7.5 million for Malawi, reflecting Madonna's ongoing philanthropic efforts.
Becoming Madonna, now streaming on Sky Documentaries, explores not only the artist's rise to fame but also the personal relationships that shaped her journey.
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