20. Bret Michaels
Appeared on: Rock of Love with Bret Michaels (2007-2009)
The guy from Poison managed to score a dating game show in which 25 women competed for his affections. "Shockingly," the winner said she didn't actually have any real feelings for the rocker-leading to him taking a second and third shot. Not surprisingly, those efforts proved just as fruitless. Still, it could've been worse. He could be still known as that guy from Poison.