You know the phrase "In like Flynn?" Yeah, this dude was Flynn. The rakish charmer best remembered as the original tights-wearing Robin Hood had the kind of boyish good looks that could help you get away with anything. Scratch that. It turns out he could get away with almost anything, but first a little background. Flynn started out using his charms for no good early on. He was expelled numerous times from school, including once for "bedding a laundress." Fame only fueled his taste for booze and women. Once he hit the big time, he snuck around on his wife like it was his job. The MGM PR department had that on lock though, even going as far as to have Flynn pen an essay on Hollywood morality.

Flynn was ultimately too much of a bad boy for even the best in the PR game. Things started to go downhill for Flynn and fast in the 1940s. He slapped a gossip columnist, began taking mysterious trips to Mexico, and developed an alleged taste for underage girls. A trial for two counts of statutory rape didn't stop Flynn (he beat the charges, though the evidence looks pretty grim), who continued to debauch himself so much that he is rumored to have been unfit for military service due to his raging alcoholism and collection of venereal diseases.

Eventually, Flynn's actions took a toll on him. He aged into a life of hepatitis, liver failure, and acting on television. Remember, back then they didn't make shows like Breaking Bad; television was where you went if your career broke bad.