4. Paris Hilton
Paris Hilton has always been a hot mess, and she generally wraps herself up with guys who plain suck. They usually have a lot of money and a drug problem; one cannot count how many times she has been pulled over and found with drugs and a bad boy. Her journey started with Rick Salomon and a sex tape, and has recently ended with Swiss businessman Thomas Gross, who looks to be an upstanding gentleman (but we’ll have to wait and see). SEE ALSO: Top 10 Male celebrities with the biggest penises (With Pictures)
As for her past indiscretions, they include Paris Latsis (remember the whole Paris and Paris phase?), Randy Spelling and Tom Sizemore.
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