10 Best Heels From WWE's Attitude Era, Ranked
Daniel Foster
Published Mar 28, 2026
The Attitude Era was a red-hot era for WWE at the end of the 1990s and start of the 2000s, and it featured some of the greatest professional wrestling acts and characters of all time. It featured some of the best babyfaces in history in “Stone Cold” Steve Austin, Mick Foley, The Undertaker, and many more, but they needed some all-time great heels to contend with.
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Some of the most entertaining, arrogant, cowardly, and evil characters emerged throughout the Attitude Era, many of whom became WWE legends because of it. Battles between heroes and villains is what professional wrestling is all about, and the Attitude Era did it in a great way. Of course, this will all be objective, but many will agree that these competitors are still among the greatest heels of the time.
10 William Regal
William Regal was an underrated part of the Attitude Era for sure, but he was one of the best heels of the era. It was his time as the WWE Commissioner where he really shone.
He was a brilliant authority figure, and whilst his humorous side did lead to a face turn, he would quickly turn heel once again. He was good at both being nasty and silly, showing a lot of range as a bad guy.
9 Mick Foley
As both Cactus Jack and Mankind, Mick Foley was an all-time great babyface in the Attitude Era, but his spell as a heel was also tremendous, and in truth it should have lasted for far longer.
His heel turn displayed the wonderful promo work he could do as a bad guy, and his run as a heel Dude Love made for a brilliant feud with “Stone Cold” Steve Austin. Even in a short space of time, Mick Foley was one of the best heels of the era.
8 Steve Austin
The Attitude Era was coming to an end by the time Steve Austin turned heel, and whilst it was nowhere close to the quality of his time as a babyface, he was tremendous in his heel role.
His promo work was top notch, his time teaming with Triple H in the Two-Man Power Trip provided some great content even though it was short-lived, and the way he continued being himself but with a meaner streak almost made him feel more dangerous. However, it was only a fairly short spell and fans just wanted to cheer him, so he is down the list a little.
7 The Undertaker
The Undertaker’s time as the “Lord of Darkness” and leader of The Ministry is one that was hit and miss for some fans, bordering on the line of being too spooky and goofy.
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However, when it worked, he was one of the most perfectly executed magical heel characters of all time. His sadistic and demonic side really shone during the Attitude Era, and he engaged in some unspeakable acts at times.
6 Chris Jericho
Chris Jericho’s Attitude Era heel work was fantastic. He played such a convincing whiny, slimy, and egotistical heel who would do anything to win - and complain if he didn’t.
He didn’t shy away from humiliation, getting his comeuppance in a satisfactory manner like all good chicken-poo heels. His involvement in the Attitude Era was a little understated at first due to his time in the midcard, but he gradually rose up the card. He was sometimes overshadowed though, and that means he isn’t higher ranked here.
5 Kurt Angle
Kurt Angle’s arrogance which was backed up with his flawless transition into the professional wrestling world made for one of the quickest ever ascents up the card for a new heel.
Angle’s ability to both be serious and funny made for a very fascinating character who could turn any content into absolute gold. Angle was a wonderful part of the Attitude Era and his heel work was certainly up there with the best, though perhaps others with more of a mean streak were even better than him.
4 Stephanie McMahon
Although Stephanie McMahon did step into the ring on occasion, she is a case of a mostly non-wrestling personality being among the very best heels of the Attitude Era.
She became the spoiled brat “daddy’s girl” who had a vicious streak inside of her. She wanted to have all the control and attention, and she played that role to absolute perfection, using family members and wrestlers alike to reach the top.
3 Triple H
Whether it be leading a heel version of D-Generation or joining up with The McMahon’s in various ways, Triple H was no doubt up there with the best heels of the Attitude Era.
He had such a way of coming across completely unlikable and vicious, with a powerhouse style and incredible mic skills too. His partnerships with Stephanie McMahon and Steve Austin were notable, and he was able to display a whole manner of different styles of heel work. His Ruthless Aggression Era heel work was arguably even better, and it may have allowed him to challenge for top spot, however he was a few steps below in this time frame.
2 The Rock
At Survivor Series 1998, The Rock turned heel and became the “Corporate Champion”, joining Vince McMahon as his poster child number one guy. He thrived in this role, showcasing a devastating mean streak along with undeniable charisma.
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He was cocky, arrogant, mean, and hilarious all at the same time, and there has perhaps never been quite a heel like him in the business. He was a wonderful foe for the likes of Mankind and Steve Austin during these years. If it weren’t for his superior, he would’ve been the best heel of the Attitude Era.
1 Mr. McMahon
Mr. McMahon is not only the best heel of the Attitude Era, but arguably the best heel in WWE history. The character revolutionized the concept of heel authority figures in a major way, and he helped to lead the charge in the Monday Night Wars.
He was the epitome of pure evil, and fans loved nothing more than to see him get his comeuppance. McMahon would put himself in a whole manner of humiliating circumstances which helped to balance the punishment he dished out on his wrestlers too. His feud with Steve Austin was the peak of the Attitude Era.
