2. Charlie Sheen
While many would think of celebrity bad boy Charlie Sheen as the “criminal” in his relationships (he recently revealed that he is HIV positive), he actually dated someone who did jail time. Sheen was in a relationship with adult film star Ginger Lynn, who did four years for tax evasion. However, if being erratic and saying hurtful things to exes were crimes, Charlie would definitely have to do some time of his own. These days, Sheen is living a more quiet life, and has been discussing his health diagnosis. One of his ex wives, actress Denise Richards, and is also supporting him, and helping him raise his children, including his twin boys with ex-wife Brooke Mueller.
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