3. The Undertaker (2001)
In early 1992 The Undertaker saved Miss Elizabeth from a Jake Roberts chair shot and catapulted his way to a spot as one of the most popular babyfaces in the WWE. Not only did fans respect his character and his matches, they also respected his loyalty to WWE, as he never wavered from the company like so many others did. The Phenom finally turned heel in late 1998, and became an excellent rival for Stone Cold Steve Austin. Taker disappeared from the WWE in September of 1999, and when he re-emerged in May of 2000 he was an entirely different character than the Deadman of years before. Rather than coming to the ring to "The Funeral March" and complete darkness, he rode to the ring on a motorcycle to music by Kid Rock and Limp Bizkit. The fans were happy to have The Undertaker back, and embraced his new character direction. Yet the Undertaker's time as a face was cut short when he turned heel in November of 2001 by attacking beloved announcer Jim Ross. The problem with The Undertaker's heel turn was that continued to be a trash talker who backed it up by taking on all comers. Sure, he made some nefarious moves like beating WWE rookie Maven all over the arena at Royal Rumble '02, and attacking Ric Flair's son, but he never had the vulnerability associated with an effective heel. WWE instead tried to get fans on board the heel turn by having Undertaker do such dastardly things as...walk to the ring instead or riding his motorcycle, and...coming out to a generic instrumental rock theme instead of "Rollin'". Needless to say, it didn't work. The Undertaker was a face again by the Summer of 2002, and to this day has remained a fan favourite.