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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. 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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  4. 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 and...

  5. Nov 13, 2022 · Sean Penn was married to Madonna for four years before their split in 1989. He divorced actress Leila George in 2022 after almost two years of marriage. By. Sophie Dodd. Updated on November...

    • Sophie Dodd
  6. 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.

  7. 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.

  8. Jul 2, 2021 · Unlike True Blue, however, Madonna’s marriage to Penn didnt endure. The relationship ended in divorce after four years, countless arguments, endless clashes with the paparazzi, and one ...