17. Madonna & Sean Penn
Rumor has it that Sean Penn is an absolute jerkface, so of course Madonna would marry him. Let us set the scene: Sean has been accused of being violent, angry, and having an affinity for alcohol. All of that adds up to bad news for any woman who chooses to be his girlfriend or even worse, wife. And that is just what Madge did. Back in 1987, Sean was in the headlines for hitting Madonna with a baseball bat. Around that time, he was also facing charges for acting violently toward an extra on the set of a film. In another instance, Sean reportedly bound Madonna to a chair for 9 hours. Gross.
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