Top 10 Iconic WWE Heels of All Time

Wrestlers either turn fan favorites or heel. That’s the reality of the wrestling business. Floating in between heel and face most likely means a short lived career in need of rebranding. Thanks to iconic WWE heels, wrestling fans have witnessed some of the best storylines in wrestling. Without these villains, wrestling would be too boring.

Of course, there are some exceptions to the heel persona. For instance, you have the NWO which was initially packaged as the bad guys. They eventually turned out to be a fan favorite because of their anti-establishment representation. There is also Stone Cold who could’ve been one of the most notable WWE heels of the 90s, but turned out a fan favorite for the same reason as NWO.

Heels get booed by fans, but help develop the character of protagonists. Who are these wrestlers that we all loved to hate over the years? Here are top 10 iconic WWE heels of all time.

10. Chris Jericho

Iconic WWE Heels
Though year 2000 was more than a decade ago, there is no denying that Y2J was one of the best villains WWE ever had. The Ayatollah of Rock and Rolla was one of those superstars who entered big in WWE. He is a loudmouth and flamboyant heel who had his share of feud against the industry’s best including the Rock and Shawn Michaels.

Chris Jericho started his career in 2001 when the Y2J countdown interrupted the Rock. This was a huge introduction for Chris Jericho in WWE who came from WCW. Chris Jericho was able to beat The Rock and Stone Cold to become the very first WWE undisputed champion.

In 2008, Chris Jericho had another run. And this time around, he had a storyline against HBK. It was one of the best things that we saw from WWE’s long list of villains.

9. DX

Iconic WWE Heels
Degeneration X – Iconic WWE Heels.

If there was the NWO in WCW, WWE had their share of outlaws with Degeneration X. Composed mainly of Triple H, Shawn Michaels, Chynna and the New Age Outlaws, they have defined the WWE attitude era. What made this stable as all-time iconic heels is their devil may cry attitude.

Degeneration X, during their time, were both protagonists and antagonists. What made them an iconic stable in the WWE were their crazy antics including going to WCW in a tank!

Also, DX was able to redefine their superstars. HBK finally found a character that suits well even for the male fan demographic of the WWE. We’ve seen the rise of DX especially at the height of their popularity versus Stone Cold Steve Austin which even included Mike Tyson in Wrestlemania XIV.

WWE attempted to bring back DX a couple of times in order to get their fans from the Attitude era back. However, gone are the heydays of the DX.

8. The Rock

Iconic WWE Heels
The Rock may have been so good at portraying his role as the people’s champ that we forgot how good he was as a heel. In fact, he first made his transition into major heel when he sided with Vince McMahon’s corporation in Survior Series 1998. Since then, he was groomed to become the champion for the company.

What made him in our list of iconic WWE heels is his ability to get the audience to really hate him. If you’ll remember his I Quit Match against Mankind, it was one of the most brutal matches in the company’s history. While Mick Foley’s family was at ringside, he delivered chair shot after chair shot to the head of his opponent.

The peak of Rock being heel was during Wrestlemania XV. He eventually lost the title to Austin in an epic Wrestlemania match for the ages.

7. Bobby “The Brain” Heenan

Iconic WWE Heels
Who says that only wrestlers make it in our list of iconic WWE heels? Bobby “ The Brain” Heenan was able to handle the likes of Andre the Giant and Mr. Perfect. But what made him the perfect WWE heel was his ability to talk to the audience. As the mouthpiece of his clients, Bobby “The Brain” Heenan made fans hate on his clients so much. And for a manager, he made an amazing job. He made it easy for wrestlers to get the exposure that they need as heels of the company.

6. Shawn Michaels

Iconic WWE Heels
Shawn Michaels was part of the Degeneration X, the stable that defined a generation of WWE fans. Other than that, let’s not forget that Shawn Michael’s career include other historic events in the company as well.

In 1985, Shawn Michaels together with Marty Jennetty had a successful run as tag team partners. In 1992, The Rockers formally split when Shawn Michaels attacked his tag team partner signaling his switch from face to heel. This was also a transition that defined Shawn Michaels as he was reborn as the Heart Break Kid.

There was the time when Vince McMahon screwed Brett Hart. Shawn Michaels getting the belt because of the screw job was one of the best moments of Shawn Michaels as a heel.

Also, he played the role really well especially as the commissioner of the WWE during the attitude era. He was able to throw stipulation after stipulation which made him a known figure in the Corporation.

5. Rowdy Roddy Piper

Iconic WWE Heels
Another wrestling villain of the 80s that made it in our list of iconic WWE heels is Rowdy Roddy Piper. If it wasn’t for Roddy Piper, Hulk Hogan wouldn’t be as big as he was during the 80s to the early 90s. He was able to get into the skin of fans from breaking a coconut into Jimmy Snuka’s head to beating a small person in the Piper’s Pit.

The peak of Piper’s career as Heel was when he headlined Wrestlemania along with Paul Orndoff against Mr. T and Hulk Hogan himself.

4. Iron Sheik

Iconic WWE Heels
One of the things that WWE did best was to merge make believe with reality. They have developed story lines that have some relevance to the current political situation. While the US is dealing with Iran in real life, it was Hulkamania who was dealing with the Iron Sheik.

Iron Sheik was able to exemplify the foreign heel during the 1980s. Iron Sheik was originally from Iran’s Greco-Roman Wrestling team in the 60s. Knowing the wrestling crowd, he was able to draw boos in every arena that he ever went to.

3. Triple H

Iconic WWE Heels
From Hunter Hearst Hemsley’s royal persona with Regal, he was able to break away and become the leader of Degeneration X. Years later; he was able to re-invent himself again to become the Game. Many consider Triple H’s success because of his union with Stephanie McMahon. In reality, it was more than that.

General ring and mic skills combined with an intimidating physique, this made Triple H as one of the most iconic WWE heels in history. And the good thing about Triple H is his ability to adapt as an instant fan favorite or heel. He had his run with some of the old and new WWE superstars including Mick Foley, The Rock, Undertaker, Shawn Michaels and Stone Cold Steve Austin.

The Cerebral Assassin was able to win the championship 13 times in different sneaky ways possible. However, there is no denying that Triple H is top WWE material has he was able to showcase historic matches including Hell in a Cell, ladder match and Iron Man Match.

2. Ric Flair

Iconic WWE Heels
Ric Flair is one of those rare gems that made it through the years in the wrestling business. Ric Flair made a career at becoming a heel. And in fact, this is why he is among the most iconic WWE heels in history of the company.

Ric Flair has the ability to get the fans to hate him. And guess what, he did his job well. He’s stylin’ and he’s profilin’ but no other superstar comes close to how Ric Flair portray his heel character.

He was a 16 time world champion, and during his heyday could provide an entertaining match with most any superstar out there. He is famous for his slaps to the chest that gets the crowd go “WHOOO”. And of course, he has an arsenal of submissions as well including his figure four leg lock finisher.

During the latter part of his career, Ric Flair together with Triple H, Batista and Orton formed the Evolution. It was a stable which included the past, the present and the future of the company.

1. Vince McMahon

Iconic WWE Heels
Vince McMahon is a hands on owner of the company. And one of the things that made WWE what it is today is Vince McMahon’s ingenious character development strategies that included himself as a major heel in the company.

He and his family are involved in the company by being part of the storyline. Vince McMahon capitalized on the fact that most people hated their bosses. He was “The Man” who doesn’t want you to succeed. During the Attitude era of the sport, Vince McMahon became part of the biggest storylines the company ever produced with the help of Stone Cold Steve Austin.

Stone Cold was the anti-hero that everyone loved. Anti-establishment with a devil may cry attitude, Stone Cold and Vince McMahon was able to catapult Raw’s ratings during their Monday Night Wars against Ted Turner’s WCW.

Vince McMahon and Stone Cold’s rivalry peaked after the end of an era match. Stone Cold defeated the Undertaker in a First Blood Match.

Without the villains, things wouldn’t be too exciting. WWE has been able to develop wrestling careers based on the heel persona. Do you agree with our list of WWE heels?

Top 10 Iconic WWE Heels of All Time

  1. Vince McMahon
  2. Ric Flair
  3. Triple H
  4. Iron Sheik
  5. Rowdy Roddy Piper
  6. Shawn Michaels
  7. Bobby “The Brain” Heenan
  8. The Rock
  9. DX
  10. Chris Jericho

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