23. Bret Michaels

Cowboy Hat, $27
Affliction T-shirt, $58
Wig, $19 
Leather Cuff, $24 
Metal Bracelet, $20
Rock of Love DVDs, $20
Ray-Ban RB3471, $110

To us, this balding dude is just the lead singer of a one-hit wonder hair metal band. But have you seen the chicks he pulls on VH1's "Rock of Love?" To them, he's a god. The girls are all trashy, tattooed, stripping trainwrecks, but that's exactly what we want on Halloween. Give us that damn wig and bandanna, we'll practice singing "Every Rose Has Its Thorn" and wake up with new venereal diseases.