#1 Sting - The Crow & The Joker
Sting was one of WCW's biggest, most popular and best superstars of the early 90's. As WCW and the times changed, however, so would Sting.
Sting had been playing the same colorful face paint wearing happy and always smiling superstar for a long time. When WCW turned Hulk Hogan heel, ditched the red and yellow and embraced the NWO, it to was time for a big change to Sting. After the NWO brought in a 'fake Sting', whom many believed was the real Sting, the Stinger felt betrayed by everyone and teased leaving WCW in a promo.
Sting returned the following month, dressed in all black and wearing a black trench coat, with black painted around his eyes, and white face paint being added weeks later. It would be a look that would remain with him for the next near 20 years.
Sting revealed that the look was originally thought of by Scott Hall, and Scott described it as a 'Marilyn Manson look'. Due to the coincidental similarities to what Sting wanted in the character, however, WCW took a direction that was more of an inspiration of the Brandon Lee's role in the critically acclaimed 1994 epic The Crow.
After playing this role for over 4 years in WCW and over 6 years in TNA Wrestling, Sting changed up the gimmick in 2011, dubbing himself 'Joker Sting', with his character now being a tribute of sorts to the clown prince of crime, particularly the version played by the late Heath Ledger in the ultra-successful 2008 epic The Dark Knight. He played this version for the better part of his final 3 years with TNA, before joining WWE as 'Crow Sting' in 2014.