8. Kid Rock

True to the rock-star stereotype, Kid Rock has had his share of blond actresses, pornographic actresses and lingerie models, with Pamela Anderson leading the pack, even though he’s far from physically attractive.

The list of pornographic actresses who have been linked to Kid Rock over the past 20 years includes Midori, Briana Banks and Jesse Jane.

When Rock wasn’t dating adult-film stars, he enjoyed the company of actresses Conchita Leeflang, Erin Naas, and models Krista Ayne and Alyssa Lipsky.

Needless to say, the most famous of all Rock’s ladies are Pamela Anderson and Paris Hilton. Yep, we know you forgot about that fling!

Kid Rock’s looks could hardly have been a factor in his hook-ups. Mind you, Kid Rock gained his celebrity status by being a singer, which certainly helped, but as for the wealth part, he was born rich anyway.