Kid Rock. (12/15)

The musician has dated his fair share of adult film stars and at times it seems that may be the main characteristic he looks for in women. There was Jesse Jane (real name Cindy Taylor), whom he allegedly dated for around a year in 2004, and, in 2006, there was Briana Banks (real name Briana Bany). And, if you believe his songs, there have been countless others.