The art of the heel turn can change the future of a wrestler regardless of which promotion allows it. Most wrestlers have revealed in interviews that they prefer to play the traditional villain role of a heel over the babyface hero. It is an easier and fun experience to convince the audience to hate you rather than winning them over to love you. Despite the position typically leading to more success, not every talent to get a heel turn booked will find success with it.
A combination of poor execution, bad booking, the wrong talent and horrible timing can lead to the fans refusing to jeer the heel. Silence, confusion or even cheers have come from these moments that were meant to feature the next big villain act. Find out just how badly things turned out for these ideas. All ten of these wrestlers had heel turns that just did not work out as planned.
10 Steve Austin
The top historical instance of a great wrestler having a poor heel turn featured Steve Austin’s character change in the main event of WrestleMania 17. The aftermath of Austin uniting with former rival Vince McMahon after the win as a heel was a poor decision.
Austin admitted many times on his podcast that he wishes he stunned McMahon right after the match and considers the turn the second biggest regret of his career after walking out. The heel turn did not work out due to fans stil wanting to cheer Austin. He did get some boos, but the peak of his heel work mostly consisted of comedic backstage segments.
9 Sting
Sting is one of the few wrestlers that rarely went back and forth in the face and heel roles. Everyone remembers Sting for his face run since it was the role in which his greatest moments as a beloved iconic character in WCW, WWE and Impact Wrestling.
WCW tried to turn Sting heel in 1999 by having him align with Lex Luger to cheat Hulk Hogan out of the WCW Championship. A combination of the fans loving Sting and disliking Hogan’s stale recreation of the 80s face character led to Sting getting cheers when stealing the title. WCW turned Sting face weeks later.
8 Chavo Guerrero
The passing of Eddie Guerrero shocked the wrestling world and fans were heartbroken to lose the legend at such a young age. WWE tried to use that emotion to add to the story of his loved ones on the WWE roster. Rey Mysterio would win the World Heavyweight Championship at WrestleMania 22 in celebration of his best friend.
Things would escalate to a less honorable extent when Chavo Guerrero turned heel to cost Mysterio the title to Booker T. Chavo was portrayed as bitter and jealous of Rey honoring Eddie more than his own relative did. The angle came off poorly and fans did not care about Chavo moving forward.
7 Big Cass
The tag team of Enzo Amore and Big Cass had expectations to become the next hot act for the tag division. However, their limitations in the ring slowed down their momentum on the main roster. WWE started to have backstage issues with Enzo butting heads with others in the locker room.
A move was made to turn Cass heel and give him the big push moving forward. It just did not work to his advantage as fans had no interest in him without Enzo and vice versa. WWE gave Cass one final shot in a program with Daniel Bryan that culminated in him getting released.
6 Rob Van Dam
Rob Van Dam is the perfect example of a wrestler that was meant to be a face. Aside from a short run before becoming a top star, Van Dam was a face for almost the entirety of his time in pro wrestling. WWE tried to change this during the Invasion storyline.
RVD joined the company as a heel uniting with the WCW/ECW brand to take down WWE. Fans instead chose to cheer Van Dam as the one face from The Alliance group. WWE was forced to portray RVD as a face and would not change that for the rest of his run.
5 Jeff Hardy
TNA made many risky decisions to try to compete with WWE. The biggest mistake came when Hulk Hogan and Eric Bischoff tried to form a new version of the nWo known as Immortal.
Jeff Hardy played the role of 1996 Hogan by turning his back on the fans to win the TNA World Championship as a villain. The heel run did not work out and Immortal turned into a train wreck. This decision helped sink Impact further beyond the point of redemption.
4 Shawn Michaels
The second chapter of Shawn Michaels in WWE featured him returning from 2002 to 2010. Michaels closed the doors on prior issues that ended his first top run in disappointment. The return featured Michaels receiving huge support from fans. Michaels remained a face during this run aside from one heel turn.
A dream match with Hulk Hogan in 2005 forced Michaels to turn on Hogan for about three months. Michaels did receive jeers in Canada for referencing his issues with Bret Hart, but most fans supported Michaels over Hogan. The heel turn ended one night after the dream match.
3 Goldberg
WCW was criticized for turning wrestlers from faces to heels and vice versa during the Monday Night Wars. Vince Russo took it to the next level by having WCW hero Goldberg turn heel in 2000. Goldberg was only a few weeks into his return from an injury leading to the turn.
Fans did not enjoy losing out on their favorite superstar so quickly after he was back. Goldberg has admitted in multiple interviews that he disliked playing the heel character. WCW would turn his back face just a couple of months later.
2 Dean Ambrose
The most recent major instance of a heel run going poorly featured Dean Ambrose turning on Seth Rollins. Ambrose attacked Rollins right after they won the Raw Tag Team Championship on the night Roman Reigns announced his battle with leukemia.
The crushing nature of the turn led to the potential of a strongly disliked villain. WWE sadly took Ambrose’s character to more comedic levels. The feud between Ambrose and Rollins was viewed as a disaster and The Shield reunited again just a few months later when Reigns returned. Ambrose’s unhappiness with the turn was reportedly a major reason in his desire to leave WWE.
1 Rikishi
2000 was arguably the greatest year in WWE history with numerous superstars in the main event picture leading to amazing moments. Steve Austin returned from an injury with a red-hot storyline of trying to find his attacker to run him over with a car that wrote him off a television in late 1999.
WWE turned Rikishi heel as the big reveal to the mystery. It was a reward for Rikishi’s great run as a face, but fans did not buy him as a top heel. WWE gave up on the angle within a few weeks and wrote the cop out of Triple H hiring Rikishi to run over Austin. Triple H would replace Rikishi as the top heel against Austin to end the year.