Show: The Pickup Artist, VH1
While the two seasons of VH1's The Pickup Artist definitely had their fair share of herbs and creepers passing through, none ever really held a candle to the sensei himself, Mystery. To this day, we still can’t wrap our heads around why the eye-lining ladykiller managed to bag so many girls, despite his palpably date-rapey vibe and preference for fuzzy Jamiroquai hats. Watch him here as he and his faithful wingman, Matador, hug it out with a series of unsuspecting dames.