The Attitude Era offered up arguably the best period in professional wrestling history – at least the most exciting in WWE history for sure. Throughout the years of 1997 to 2002 when it officially ended, there were several massive babyface and heel turns – sometimes even multiple turns for certain individuals.
This will look at the best heel turns of that era, and it will take multiple factors into account. The moment itself will be judged on how well executed it was, and the aftermath of a heel turn will also be taken into account as well. Sometimes the moment outweighs the booking and vice versa.
10 Kurt Angle
Kurt Angle’s heel turn was one of many turns during the Invasion angle and battles between Team WWE and The Alliance, and whilst many of these moments and turns were meaningless, Angle’s was one of the better ones.
In one of the many multi-man brawls during this feud, Angle ran down to the ring to seemingly help his allies, only to nail them all over the head with a steel chair. The fans were shocked, booing him out of the arena, in what was a great moment during what was ultimately a poor storyline.
9 Edge & Christian
After breaking away from The Brood and The Ministry of Darkness, Edge & Christian began wrestling as babyfaces. However, over time they began showcasing arrogant tendencies, bringing in annoying humor and goofy personalities that fans loved to hate.
There wasn’t a huge moment for their heel turn, but the development of it was fantastic, and the way they built up this new gimmick was well done. They helped to lead the tag team division during this era, becoming one of the most celebrated teams of all time following their heel turn.
X-Pac’s tag team with Kane was a fun act, but all ultimately turned out to be a ruse when X-Pac gave him a low blow during a tag team match, prompting D-Generation X to beat the big man down.
It was a shocking moment as all signs pointed towards Kane being a unique addition to the group. X-Pac shouting insults down the mic as he led a devastating attack on Kane. The monster became sympathetic here, which is testament to the well done heel turn from X-Pac.
7 Triple H
Speaking of X-Pac, he was also on the receiving end of a strong heel turn during the Attitude Era, as Triple H attacked him and sparked the fall of D-Generation X.
At WrestleMania 15, Triple H helped Shane McMahon win the European Championship from X-Pac, joining The Corporation faction in a game-changing moment. The turn itself wasn’t necessarily the most high profile due to Triple H not yet being a main eventer, but it would lead to him becoming a huge star in WWE, becoming WWE Champion over the next few months, so that elevates it.
6 The Undertaker
The Undertaker gradually became darker throughout 1998, and eventually became a lackey of Vince McMahon. His defined heel turn came when he was revealed to be the one behind the death of his and Kane’s parents. The formation of the Ministry of Darkness sparked a heel Undertaker for the first time in years.
It was a great turn, with him truly coming across as an evil entity. He was darker, smarter, and more sadistic than ever. Some of the details and soap opera style drama with Kane perhaps brings it down a few places, but it was still strong nonetheless.
5 Stephanie McMahon
Prior to turning heel, Stephanie McMahon was presented as the innocent daughter of Vince McMahon. At Armageddon 1999 show, Stephanie turned on her father and revealed that she and Triple H had been in cahoots all along.
This opened up a whole new side to her, and she showcased the abilities of being an all-time heel. The McMahon-Helmsley reign over WWE was very entertaining, and it sparked from this well-executed heel turn which was among the best of the Attitude Era.
4 Mick Foley
Mick Foley’s 1998 heel turn is one of the more underrated of the Attitude Era, but it was no doubt among the very best. He came out battered and bruised, and cut a tremendously authentic promo in which he displayed his frustrations with the fans. While this an overdone trope nowadays, Foley came across real and true with his words.
Foley would damn the crowd and leave, saying that they weren’t seeing Cactus Jack again. He would later emerge as Dude Love, targeting Steve Austin as a heel. This turn should be held in far higher regard.
3 “Stone Cold” Steve Austin
Steve Austin turning heel and shaking hands with his sworn enemy at WrestleMania 17 is one of the biggest heel turns of all time. The moment was huge, shocking, and it broke the hearts of fans.
Austin’s time as a heel was up and down, which robs it of the number one spot, but the moment itself brings it high up this list as it was an industry-changing moment.
2 The Rock
After his expulsion from the Nation of Domination, The Rock briefly became a babyface. However, this was short-lived as he pulled off one of the better heel turns of the Attitude Era.
The Rock and Mankind were part of a great double turn as The McMahon’s aligned with The Rock and issued a brutal and vicious beatdown of Mankind. The Rock became WWE Champion and was the Corporation’s poster boy. His face run was going well, but he went on to reach dizzying heights as a heel following this.
1 Mr. McMahon
Following the Montreal Screwjob, Vince McMahon brought himself into the picture as a full-time on-screen character, turning heel in a wonderful promo as he claimed “Bret screwed Bret”. His delivery was fantastic and it unlocked one of the greatest heel personas ever.
This was arguably the best heel turn of the Attitude Era, and it was certainly one of the most important.