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Madonna · S4 E1
Sean Penn
The marriage that moved faster than anyone could track, and the volatility that came with it
Point Dume, Malibu, August 16, 1985. Five media helicopters circle the clifftop as Madonna walks toward an altar in a strapless gown, marrying Sean Penn on her twenty-seventh birthday while rotor wash turns her veil into a flag of surrender.
"The Power of Good-Bye" (1998). Thirteen years after marrying Sean Penn, Madonna releases a song about the strength it takes to walk away from something destroying you. Directed by Matthew Rolston, the video moves through a dreamlike sequence of intimacy and separation, with chess pieces standing in for the power games inside a relationship.
The Courtship
Sean Penn first sees Madonna on the set of the "Material Girl" video in January 1985. He walks onto the lot at A&M Studios in Hollywood, watches her perform the Marilyn Monroe routine, and decides he will pursue her. Within weeks they are inseparable, and within six months they are engaged.
“He was like nobody I had ever met. He was not afraid of me, and that was incredibly exciting. Most men were.”
— Madonna, on meeting Sean Penn
TAP TO REVEAL: What did Sean Penn do about the paparazzi helicopters at his wedding?
Point Dume, Malibu
The clifftop estate where Madonna and Penn marry on August 16, 1985. The Pacific Ocean spreads out below, but nobody at the ceremony is looking at the view. The sky is full of helicopters, and tabloid outlets have paid upward of $100,000 for aerial access to the most famous wedding of the year.
The Penn Years
White Heat
From True Blue (1986). Named after the 1949 James Cagney gangster film, this is Madonna's love letter to her husband's world: method acting, explosive characters, the romanticization of outlaws. It opens with a spoken Cagney sample and never slows down. The closest she comes to a rock song in the 1980s, and the most direct sonic portrait of life with Sean Penn.
How many times has Madonna been married in total?
The marriage is volatile, but it is also creatively electric. Next episode: the making of True Blue, the record she dedicates to Penn and the album that transforms her from an American pop star into a global phenomenon.
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