#9 Goldberg: 2000
'It's not just WWE who have had failed heel turns. In 1996, WCW Vince President Eric Bischoff made the incredible decision to turn the then most popular superstar of all time, Hulk Hogan, heel. And it worked!
By 2000, WCW's most popular Superstar was Goldberg. WCW were in a ratings slump and new head of creative Vince Russo looked at the Hogan heel turn as inspiration for something big, turning Goldberg heel. Hoping it will have the same reaction and ratings boost as Hogan's did, they made a wrong move.
Clearly, the heel turn just didn't click. At The Great American Bash, Goldberg turned on Kevin Nash during Nash's World Championship match against Jeff Jarrett and turned into a villain for the first time in his career, aligning himself with Russo's New Blood faction.
This didn't last long as fans just couldn't accept Goldberg as a heel. Although his initial turn received boos, he was still cheered during matches and segments. WCW realized this and turned him face, less than three months after the Bash.