WWE’s Greatest Heels: Attitude Era Edition

The Attitude Era of WWE (fka WWF) will always be looked back on fondly. For many wrestling fans, it is when they fell in love with the company. It contained some of the best characters in company history. Characters like The Rock and Stone Cold Steve Austin had us believing in wrestling again, and the money and ratings came rolling in.

Babyfaces of the Attitude Era were great, but they wouldn’t have achieved such greatness were it not for some fantastic heels that stood across from them. These heels were so hated that the fans came out in droves to see that they finally got what was coming to them. They were the greatest of their era, and they are described below.

WWE’s Greatest Heels for the Attitude Era

Stephanie McMahon

The Billion Dollar Princess is not only one of the greatest heels of this era, but one of the best in the company. There might be no other woman who is as hated as she was.

The second she moved her way through the curtain the chorus of boos rained down upon here. It became hard for her to get any words in when she hit the ring, as the crowd would drown her out.

The eldest McMahon’s power and money were what made her hated. She was born with a silver spoon, and she leaned into this character. She abused every ounce of power she had and was rarely put in her place.

When she was it was a special occasion and that made her comeuppance that much more important. Stephanie McMahon was the epitome of the spoiled rich kid, and there was no woman who came close to her level of heat.

The Undertaker

The Undertaker was always a character who struck fear into the hearts and minds of the audience. His black garb and pale skin were a terrifying sight for anyone, but it was during the Attitude Era that he amped everything up to 11.

Forming his gothic group, the Ministry of Darkness, The Undertaker became the thing of nightmares. He became the Lord of Darkness. His entrance was darker, his character was darker, and he had no problem sacrificing anyone who opposed him.

Some of his most famous segments, during this time, resembled something out of a horror movie. We were both terrified and in awe of everything he did during the Attitude Era. He was the villain that every hero needed and the one we couldn’t take our eyes off of.

Bret Hart

Sometimes the best heels are the ones who are justified in what they are thinking. A perfect example of this is the path that Bret Hart took towards being one of the heels that jump-started the Attitude Era.

Bret Hart had been disenfranchised by WWE. He had been screwed in many matches, and he felt as if the company he worked so hard to hold up had passed him by.

The management and fans were going in a different, more edgy direction, and Hart couldn’t stand it. His vicious promos were great and checked all the boxes one needed to get heat from the fans.

Hart waged a war on the top face stars. They represented everything he hated about wrestling, and he continued to take the fight to them up until his timely departure. It wasn’t a long heel run for The Excellence of Execution, but it was an effective one.

The Rock

Before he was electrifying the crowd every week, The Rock had to work through the “Die, Rocky, Die” chants. But they were chants that turned him into what would become an iconic character.

Following his failed baby face run, Rocky Mavia reinvented himself as The Rock. A cocky, talented man who would use every advantage given to him to get over his opponents. Throughout his heel run, he would be intertwined with either Steve Austin or Triple H.

He was the perfect heel champion for the baby face to chase. He was arrogant enough to lord his wins over everyone, and when he would lose, it was a huge deal for everyone involved. It wasn’t too long before the fans forced a baby face turn with The Rock, but that was a testament to how great he was as a heel.

 Triple H

Triple H was the type of heel that many would aspire to be. He turned because he was obsessed with becoming World Champion, and it was this feeling that made him one of the most hated men of the Attitude Era.

There wasn’t anyone who got more hate than Triple H did. He did whatever he could to become the champion, including marrying the boss’s daughter. It gave him the power necessary to maintain a stranglehold on the main event, and he would use his clout to constantly tip the scales in his favour.

It got to the point that the fans were spewing hatred at the man who was always the champion. Even when HHH lost his title, it wasn’t long before he got it back. He was the man who didn’t care about fan perception as he rose to the top of WWE.

Kurt Angle

When introduced, Kurt Angle was supposed to be a baby face. He was a legitimate Olympic Gold Medalist and should have gotten a hero’s welcome.

Too bad that his wholesome gimmick was going to fly in the Attitude Era and he was soon hearing more boos than cheers. Luckily, WWE was smart enough to pivot off this, and thus, one of the best Attitude Era heels was born.

Angle’s wholesome gimmick turned into a better-than-everyone gimmick. Kurt would play off his real-life accomplishments, trying to be the hero that no one wanted. His exasperation at the fan’s rejection was perfect and moved towards a justified heel turn, in his mind anyway.

The Olympic medalist was the hero that no one wanted, but he kept tugging at that thread. He was better than all of us and would take every opportunity to remind the world of it.

Mr. McMahon

There is no other man who embodied what it was like to be a heel than Mr. McMahon. As owner of the company, Mr. McMahon predominantly stayed behind the scenes but, during the Attitude Era, he moved front in center as the most detestable boss that any of us can imagine.

Mr. McMahon’s war on Steve Austin made him the most hated man in the world. There was no level that he would stoop to to make sure Austin wouldn’t capture the WWE Championship. McMahon would screw over anyone he could, including his own family.

It was this level of commitment that had the fans hating everything he did. There was no line he wouldn’t cross, and no person he wouldn’t sacrifice. It was the worst human quality, and an evil that made him the worst of the worst.