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  2. Jul 31, 2021 · On January 5, 1989, Madonna filed for divorce (via The Things) for the second time from actor Sean Penn after less than four years of marriage. Citing irreconcilable differences, the Material Girl put an end to a marriage that ran rife with insecurity, jealousy and even jail time (via Cheat Sheet). Advertisement.

    • Jesse Gormley
  3. Jun 24, 2024 · While it may be old news now, Sean Penn and Madonna were once married from 1985 to 1989. And while their relationship had Hollywood’s attention at the time, rumors of their rocky marriage...

  4. Aug 16, 2023 · As the queen of pop Madonna celebrates turning 65 today, Express.co.uk takes a look back at her marriage to actor Sean Penn, who she wed on her 27th birthday back in 1985.

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    • Fran Winston
  5. May 23, 2024 · Madonna and Penn were married for four years from 1985 to 1989. They first met on the set of the movie Shanghai Surprise. Their relationship was known for its ups and downs, and Penn...

  6. Jul 25, 2022 · Madonna and Sean Penn's marriage and ultimate divorce has come and gone, but their love story is full of twists and turns. Here's how it all went down.

  7. Sep 1, 2022 · If fans recall, Madonna's been married two times, first to Oscar-winning actor Sean Penn, to whom she was married from 1985 to 1989, and then to director Guy Ritchie, in 2000. The pair,...

  8. Aug 31, 2022 · Madonna was previously married to Oscar-winning actor Sean Penn between 1985 and 1989, before she tied the knot with film director Guy Ritchie in 2000. The former couple – who share two sons,...