How Many Times Has Sean Penn Been Married?

Sean Penn was first married in August 1985, a few years after he broke out in the Hollywood scene. His wife was none other than the global popstar Madonna. According to Song Facts, Penn met Madonna while she was shooting the music video for "Material Girl." Penn was originally there to visit his former assistant

Sean Penn was first married in August 1985, a few years after he broke out in the Hollywood scene. His wife was none other than the global popstar Madonna. According to Song Facts, Penn met Madonna while she was shooting the music video for "Material Girl." Penn was originally there to visit his former assistant Meegan Lee Ochs, who was working on the set at the time. Penn reportedly locked eyes with Madonna, and it was love at first sight for both of them. The two dated for six months and tied the knot on Madonna's 27th birthday (via Showbiz Cheat Sheet). However, their relationship showed cracks a year into their marriage.

Jealousy supposedly became a major source of tension in their relationship, with Penn reportedly breaking out in random fits of rage. Penn also reportedly manhandled songwriter David Wolinski because he thought he saw the songwriter kiss Madonna, according to Showbiz Cheat Sheet. Penn's jealousy issues reportedly got so bad that he thought Madonna cheated on him with singer Nick Kamen, People reported. The "Like A Virgin" singer denied any accusations of infidelity and filed for divorce from Penn for the second time in 1989, per The New York Times.

Their divorce was made nastier with accusations of domestic abuse, which Madonna denied and defended Penn against (via Marie Claire). Despite their drama-filled divorce, Penn and Madonna remain close friends to this day.

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