3. Charlie Sheen
Back in the day it seemed like Charlie Sheen was actually “winning’ – at least to him. Now after his public humiliation and his HIV diagnosis, I don’t think even he could claim that he has not lost. It has been rumored that he had well over 500 paid sex workers as partners over his run, as well as with adult stars such as Capri Anderson, Bree Olson, and Ginger Lynn. If anyone could possibly be the poster boy for the typical dude that dates adult stars it would be Charlie Sheen except for the fact that he is not the typical anything… No one has lost so much because of horrific behavior, except perhaps Tiger Woods, who not so shockingly is also on this list. Here is hoping that Charlie has got it a bit more together as of late.
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