WWE’s 5 Best Career Heels

"Bad times don't last, bad guys do" - Scott Hall

Most wrestlers will fall into two categories: heel or face, the bad guy or the good guy. You get some that straddle the mark such as: Eddie Guerrero, CM Punk, Stone Cold or The Rock. You can also have the ones that are good at either, take Daniel Bryan for example.

The ones we look at today are the definitive heels, the ones who are bad guys through and through. The best of WWE’s despicable heels from their multi-decade spanning roster. While some may have had a run on the light side, they’ve not quite hit the mark in the way that they did on the dark.

For inclusion in this list they’ve had to have: spend a large chunk of their career in the WWE, have most of that time as a heel and they’ve not been made into a successful face. Let’s celebrate the ones who are the absolute worst in the best way.


5. The Miz

The Miz WWE

Mike Mizanin is one of WWE’s best promo guys of the PG Era, the man has talked his way to the top and has been there for a long time now. The character of a heel who believes he’s better than everybody else isn’t new, there’s a reason Flair gave him the figure-four leglock, but that doesn’t mean everybody can pull it off.

This position on the list was a difficult one, it could’ve gone to Edge, Roddy Piper, The Iron Sheik, Ted DiBiase, Charlotte Flair or one of the countless other excellent heels, though I believe The Miz has one thing above them all: you may want to boo the others for playing a great heel, but they have an underlying lovable side. You really can’t help but hate The Miz, masterful.

He may be a face these days, but it seems to be because of the focus on his reality TV show and his family, though he’s become more of a mid-carder showing up less and less. Hopefully he can break the record for most Intercontinental Title reigns before he heads fully into the Dwayne Johnson-esque Hollywood route.


4. Jake ‘The Snake’ Roberts

jake roberts
Source: WWE

Roberts is possibly my favourite talker of all time, he stood out from the shouting and bright colours of the ‘80s and ‘90s by simply talking with some semblance of calm. His smooth tone managed to captivate all who listened and had the ability to overpower his boisterous counterparts. ‘The Snake’ did something that few did at the time: every word was thought through, every word had meaning, every word was impactful, and every word made for must-see viewing.

Though the DDT may have become just another basic move in today’s wrestling scene, Jake managed to make it the deadliest finisher in wrestling at the time and do it by his aura alone. The DDT had a threat like few finishers do today, a more modern example being the RKO for context, and he made sure you knew its impact with his words.


3. Vince McMahon

vince mcmahon
The previously unknown owner of the then WWF was outed by Bret Hart after the infamous ‘Montreal Screwjob’ in which, I’ll keep it short because we’ve all heard the story enough times, Vince forced the proud Canadian Bret to drop the title to HBK in Canada via shenanigans. The now known chairman became an on-screen presence whose first target was Stone Cold Steve Austin.

The feud with Austin could be called the pinnacle of the ‘Mr McMahon’ character. It primarily fuelled the Attitude Era and regained the WWF’s foothold in the ratings war with WCW, you could argue that the WWE would not be where it is today if not for this feud; this is where Vince’s true genius can be seen.

What made the character work so well was the working-class fantasy of taking it to the authority, whether that is your boss, the government or the wealthy. The feud began in 1998 and culminated at 2001’s Wrestlemania X-7. Vince has remained a heel to this day, even if his appearances have become sporadic and his authoritarian legacy has been passed on to the younger generation of the McMahon clan.


2. Triple H

Triple H Chris Jericho
Triple H, Hunter Hirst Helmsley, ‘The Game’, ‘The King of Kings’, WWE COO, Terra Ryzing or whatever you choose to call him, Paul Levesque has been a mainstay in World Wrestling Entertainment for much of our collective wrestling memory. Triple H became the final boss of WWE during his fourteen World Championship reigns, the definitive heel that the ultimate babyface had to conquer. This becomes evermore clear when you discover that he has the record for the most Wrestlemania losses, doing the job for the likes of: The Undertaker (three times), Batista, John Cena, Danial Bryan, etc. on ‘The Grandest Stage of Them All’.

The thing that makes Triple H so hateable is how he can seemingly win all matches that he shouldn’t, the issue with that is that you don’t want him to win any matches; the proceeding issue is that he needed wins to legitimise his dominance, so either way it makes you hate him. Truly, he is the ultimate bad guy and he has the look and skill to back it up. The only thing keeping him from the top spot is his promo ability, even though he has come on over the years on the mic, he has always stood out alongside his main event peers such as The Rock and Stone Cold.


1. Ric Flair

Ric Flair
Image Source:

Ric Flair may have spent a lot of his illustrious career outside of WWE, but he’s also spent a lot of it in the WWE and has been a bad guy throughout the majority of it. Flair is arguably the greatest of all time and he has his longevity at the top to back it up. When a chop is hit the fabled Flair “Woo!” still echoes throughout the wrestling world, regardless of promotion. He may have had a couple of runs as a face, such as the 2001 co-owner of the WWF/E storyline, though they constitute a minor part of his five decade-spanning career.

Flair’s decades at the top can be contributed to two things: his ability to get people to hate him and his ability in the ring. If it wasn’t for his quality between the ropes, the character of ‘The Nature Boy’ could’ve simply gone stale, it has instead lasted a considerably long time which can be seen as a testament to Flair’s talent. He could be considered on a list such as this for multiple promotions, but i’d happily call him the best in WWE history for his performance in the ’92 Royal Rumble alone- the greatest heel display of all time.

So, there we have it, the best career heels in WWE history. I’m sure you all have your favourites, so let me know what they are in the comments below.

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