9. Sean Penn And Madonna
Ridgemont High’s “Spicoli” and 1980’s Material Girl. This relationship should have worked. To no one’s surprise, it didn’t. The two celebrities married in 1985. They were head over heels for each other. They even starred in the terrible Shanghai Surprise and Madonna dedicated True Blue, her third album, to her husband. Not unlike other relationships covered by this list.
Around this time, Penn had some unfortunate run-ins with photographers which cost him a 60-day jail sentence. He only served 33 days. Penn was also accused of striking Madonna. In 2015, Madonna denied the allegations once and for all. It only took two decades…
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