Villainous Legends: WWE’s Most Notorious Heels

In professional wrestling, a heel is as important as the babyface. Heels are often regarded as the villains and seem to embrace the dark side of things by breaking rules, cheating, and often getting entangled in underhanded activities just to get their way. They are the antagonistic forces that make heroes shine brighter and storylines more engaging. WWE has bred a few of the most notorious heels in wrestling history—that is, the really memorable ones. These are the villains who have worked to entertain the fans but, at the same time, turned out to be the very reason behind the evolution of the industry. This article reviews some of the most well-known heels in WWE history, their personas, and defining moments that made a lasting difference in professional wrestling.

1. Ric Flair

The Persona
Ric Flair, popularly referred to as “The Nature Boy,” is probably the greatest heel icon professional wrestling ever had. He was flamboyant, high fashion, and made that famous catchphrase “Wooo!”; he was nothing but arrogant and showing off. He was very cocky, the epitome of the personality a heel should have, going out there living the fabulous lifestyle one way or another and throwing his money around and showing he had everything.

Defining Moments
He truly solidified himself as a heel in the 1980s, intershed with the National Wrestling Alliance (NWA) and World Championship Wrestling (WCW), though. Those feuds he had with Greats like Dusty Rhodes, Ricky Steamboat, and Sting are the s*** of wrestling legend. But one of the most infamous things Flair ever did was during that aforementioned feud with Dusty Rhodes, where he and the rest of the Four Horsemen kept attacking Rhodes, leading to several memorable confrontations.

Impact
Ric Flair, working as a heel, left an influence that transcended generations. Paralleled by none at getting heat, Flair also knew how to work in a way that actually put his opponents over. Following Ric Flair’s lead, his rounds of promos and in-ring psychology would be the charisma template for all future heels. Continual imitation by wrestlers today, he is a timeless imprint in the annals of wrestling.

2. Vince McMahon

The Persona
Vince McMahon, from behind-the-scenes executive to one of the top television villains, as the “Mr. McMahon” character, rose to infamy in the late 1990s. Now a manager, he was then the despotic boss who would do anything to hold on to his position and power within the company.

Defining Moments
McMahon’s heel turn had actually begun several years earlier, in the Screwjob of Montreal in 1997, where he very controversially conspired against Bret Hart to lose a match to Shawn Michaels. This meld of the real and fiction began a launch into a major heel figure: the evil boss character. His long going feud against Stone Cold Steve Austin could arguably define the Attitude Era, with McMahon continually trying to keep Austin from hitting the big time. Iconic moments include Austin filling Vince’s McMahon’s Corvette with cement and the infamous beer bath.

Impact
Vince McMahon blurred wrestling storytelling into real life’s entropy with scripted drama. His feud against Austin is one of the chief reasons WWE overcame WCW in the Monday Night Wars. His run is, to this effect, biting villainy and sets many of the paradigm shifts of what authority figures were going to be moving forward into storylines, which makes him one of the most important heels in wrestling history.

3: Triple H

The Persona
Triple H is one of the most calculating and ruthlessly heel personas to tread on the canvas of the WWE. As such, this methodical thought, along with the constant rise to power, speaks of Triple H being the heel in many a storyline throughout his career.

Defining Moments
Triple H has been in the process of becoming a top heel—ever since the formation of D-Generation X (DX) together with Shawn Michaels, a step further in this transformation as he becomes a true leader. In real life, his marriage to Stephanie McMahon only furthered the perspective of him as an insatiable manipulator.
Memorable moments include his betrayal of Shawn Michaels, his “reign of terror” as World Heavyweight Champion, and his role in The Authority, a group that controlled the majority of WWE programming since the 2010s.

Impact
Heel work from Triple H would probably have to be considered one of the most instrumental pieces of work in determining the current landscape of the narrative that develops the WWE. The ability to siphon off steam from the audience and the commitment to the character he showed made him one of the most despised villains in wrestling work. More than his work inside the ring, Triple H has matured as an officer important to creative direction and talent development within the WWE.

4. Rowdy Roddy Piper

The Persona
Quick-witted and erratic, Rowdy Roddy Piper is clearly one of the most entertaining heel characters in the history of WWE. The meanstreak, the Scottishness, the kilt, and the infamous Piper’s Pit segments which ensued were what set Piper apart.

Defining Moments
The rivalry he would continue to have with the likes of Hulk Hogan was the cornerstone of the emergence of the WWE into the popular eye during the mid eighties. From the moment he smashed a coconut over the head of Jimmy Snuka to his many run-ins with Hogan, Piper remains legendary for his exploits. It made him a must-watch—a top heel if there ever was one—able to rile up audiences with a sharp tongue and brash attitude.

Impact
The contributions of Roddy Piper to wrestling went way deeper than just the in-ring work he did. Piper’s Pit was a prototype of different talk show segments in WWE, through which wrestlers could churn up the brewing characters and storylines. It is this charisma and promo skill that put Piper at a level many upcoming heels will never achieve, and kept his legacy intact as one of the greatest villains in wrestling history.

5. The Undertaker

The Persona
Although The Undertaker is very much hailed as the legendary babyface, his heel persona, especially during the ’90s starting with the “American Badass,” just depicts this character as a very versatile performer. The Undertaker, the heel, was a grim, supernatural figure that by instilling fear defeated every competitor or enemy in front of him.

Defining Moments
The heel run of The Undertaker first began by means of his debut at the 1990 edition of the Survivor Series. He was introduced by Ted DiBiase as part of the Million Dollar Team. From that moment, the aura generated by his eerie presence effectively imposed him as a top villain.
One of the largest heel turns in 1999 for The Undertaker was forming a faction known as the Ministry of Darkness. Probably the most integral stable involving black magic and mental games, it resulted in some very good feuds against Stone Cold Steve Austin and Vince McMahon.

Impact
His ability to shift from a heel to babyface at will helped somewhat in increasing his length of stay in the company. There was something added to the nature of WWE’s storytelling with the character of The Undertaker and the fear brought while he was playing heel. The influences of The Undertaker on elements of horror and the supernatural in wrestling will inspire generations of wrestlers.

6. Edge

The Persona
Edge, otherwise known as “The Rated-R Superstar,” is the craftiest and most opportunistic heel in the WWE. His character worked off controversy, manipulation, and capitalization on everything to achieve what he wanted.

Defining Moments
Edge’s heel run was elevated to another level in 2005 when he won the first-ever Money in the Bank Ladder Match and subsequently cashed in the briefcase to beat John Cena for the WWE Championship.

That became only an opportunistic move, defining his entire persona, to be henceforth named “The Ultimate Opportunist.” Edge’s affair with fellow Diva Lita, his betrayal of his tag team partner Christian, only confirmed his heel status, along with his feuds with legendary top-tier wrestlers like The Undertaker and Jeff Hardy.

Impact
Any long Edge’s reign in the top heel spot rejuvenated his career and put that exciting feeling back into WWE programming. Edge was quite ready to push the limits and totally get into the villainous persona that racked up a ton of accolades for the superstar, including multiple World Championships. Edge remains known for his heel work, which vastly influenced how the WWE would continue to use the Money in the Bank concept in their storytelling.

7. Randy Orton

The Persona
Randy Orton could have just easily been tagged as “The Viper,” as he happens to be one of the most cruel heels ever presented by WWE. Such a methodical and calculating approach was rightly matched up with his natural charisma to make him one of the more efficient villains in wrestling history.

Defining Moments
Orton as a heel started way before, coming in with his “Legend Killer” gimmick, with which he would point, rub, and defeat some of the WWE legends. His selling out of Evolution stablemates Triple H and Ric Flair to an already long list of lousy teammates sealed the deal for him as a heel. Other notations from his career include mercilessly pummeling John Cena’s father, being ruthlessly relentless over the WWE Championship, and his involvement with the sinister Wyatt Family.

Impact
Randy Orton’s ability to always reinvent himself yet still be able to keep his heel character going has done nothing less than really keep him relevant in this business, at the very top, for close to two decades since his debut. It is his psychological arousal and in-ring predicament that has beholden him to be a perennial main-eventer. The effect and influence of Orton have shown in multiple championship periods and the respect he has from both his fans and peers.

8. Brock Lesnar

The Persona
One of the most dominating and feared heels in the WWE is Brock Lesnar, the physical man with a real background in combat sports.

Defining Moments
Brock Lesnar came back to WWE in the year 2012 and started his most infamous heel run. He completely ripped John Cena to shreds at SummerSlam 2014. He delivered 16 German suplexes to John Cena, which was just a massive showcase of brutality. Secondly, Brock Lesnar broke The Undertaker’s unbeatable streak in the WrestleMania, another very important incident in establishing him as the top heel. His on-screen association with the egomaniacal Paul Heyman, who serves as his mouthpiece, enhanced his frightening persona.

Impact
Brock Lesnar personifies the true heel in the WWE. His presence incorporates an element of reality with the sensation of the unknown. When he walks through the ropes in any WWE ring in the world, it is equivalent enough to provoke “What enrolled in one of the biggest brawls of the year?” His impact on WWE was truly monumental, with his matches and rivalries at the forefront being such big draws.

9. Chris Jericho

The Persona
Chris Jericho has really been the master of versatility and charisma, as he has played both heel and babyface roles throughout his career. His ability to come out and captivate an audience with his mic skills and in-ring persona during his heelish run, especially with the “Y2J” and “List of Jericho” stages, has just been second to none.

Defining Moments
For example, his 2008 heel turn in which he became much more serious and methodical was a far cry from what he used to do in the ring. His rivalry with Shawn Michaels became so personal to him that it culminated with the act of him chucking Michaels into the Jeritron 6000; one of the most intense, personal rivalries in the history of WWE. Then again, there was his “List of Jericho” in 2016—humorously listing people who annoyed him—which also won over droves of fans.

Impact
What made him relevant at any given era of wrestling was Jericho’s numerous reincarnations of the heel persona. All of these together have been some of the best buffs-and-buffs of in-ring storytelling towards making Jericho one of the most entertaining and efficacious heels in WWE history. Jericho’s influence has gone well beyond WWE, emanating through AEW to extend across the wrestling industry.

10. CM Punk
    CM Punk, ‘Voice of the Voiceless,’ would probably round off the list of those unique heels who really did blur the line between pure villain and anti-hero. His whole rebellious attitude and outspoken nature really must have been an interesting player for most effective use among fans.

Defining Moments
The infamous “Pipe Bomb” of Punk in 2011 vented his true thoughts, voices, and feelings against the management of the WWE and was really the game-changer the wrestling universe badly needed. Sure enough, the subsequent backstabbing heel turn in 2012 with Paul Heyman led him to an egoistic personality. Even some of his feuds as a heel, particularly with John Cena, The Rock, and The Undertaker, really show his versatility.

Impact
CM Punk really added a new sense of realism and intensity to WWE with his heel persona. Contesting all the time against injustices and being himself inside that squared circle is what literally made him one of the most controversial personalities in wrestling, yet he enamored and electrified wrestling fans everywhere. Punk solidified a heel persona that continues to define current WWE character development and storytelling.

Conclusion
The heel is the most fundamental part of professional wrestling, and at times, WWE has put out the biggest and craziest baddies in the business: from Ric Flair’s flamboyant arrogance to CM Punk’s no-nonsense anti-establishment personality. These heels have come to captivate audiences and define different times in the business. Their insane skill at drawing natural heat, along with callous but ego-summoning tactics on the microphone, puts them far ahead in a true heel league within the world of wrestling. As WWE goes on and changes, the legacy of such villainous legends will only serve to inspire the next generation of heels, ensuring the art of being a wrestling villain remains as vibrant and precious as ever.