WWE's Mt. Rushmore of Best Heels from Each Era
No company in professional wrestling history has defined the business at the level of WWE.
From the founding of the World Wrestling Federation (WWF) in 1980 to its rebrand as World Wrestling Entertainment (WWE) in 2002 all the way to modern day, this is a company that has evolved with the times.
It is now such a juggernaut in the business that it can broken down into a series of eras stretching over 45 years.
The Golden Era (1980–1993) is best known for the run of Hulk Hogan at the top of the business, while the New Generation Era (1993–1997) tried to follow up with stars such as Bret Hart and Diesel at the top.
WWE reached its initial peak in The Attitude Era (1997–2002), guided by "Stone Cold" Steve Austin and The Rock. The Ruthless Aggression Era (2002–2008) highlighted the rise of many stars, though none were as successful as John Cena.
Cena would go on to dominate the PG Era (2008–2013) into the Reality Era (2014–2016) before Roman Reigns took over in the New Era (2016–present).
Each of these periods may be best known for their top faces, but every great hero needs a villain. These eras would not be complete without the best heels in wrestling.
The following list celebrates the top four heels of each era, highlighting the Mt. Rushmore of villains that help shape each era.
The Golden Era
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The rise of WWE was on the back of Hulk Hogan. He was the classic colorful babyface who would not give up no matter what challenges he faced.
Every top heel eventually had to contend with Hogan and defined their legacy by how they responded to that challenge.
Bobby 'The Brain' Heenan
This was the only era of WWE where a manager truly dominated the sport. The Heenan Family made up the majority of heels in this era.
Heenan was a constant thorn in the side of every top face, including Hogan, notably in his role corrupting Andre The Giant and turning him against The Real American.
'Macho Man' Randy Savage
While Macho Man could also be considered the No. 2 babyface of this era, it was his heel run after turning against Hogan that made the greatest mark on the industry.
The Mega Powers exploded in one of the most iconic battles of all time. Savage also made The Ultimate Warrior look better than anyone during this time.
'Rowdy' Roddy Piper
Piper is one of the greatest instigators in wrestling. His iconic promo work defined this era, even if he was never rewarded with a world title reign.
He was hated and beloved in equal measure for the way he went after everyone. The Rowdy One defined what it meant to be a brash heel and has often been imitated but never duplicated.
'The Million Dollar Man' Ted DiBiase
While other heels reached greater heights in this era, no one more consistently made an impact. DiBiase was the thorn in the side of every face.
He threw around money to get ahead but was always thwarted just before winning the big one, including almost buying himself the WWE Championship.
The New Generation Era
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This second generation is best known for Bret Hart. He took over the industry and delivered great moments but could not live up to Hulk Hogan's popularity.
However, beyond a brief failed run with Diesel at the top, this was still The Hitman's era, and his best rivals made the most of working with him.
Shawn Michaels
While WWE struggled to find a top babyface in this era, the heel at the top was always HBK. Even when the company tried to make him the top guy, it was so much easier for him to be the villain.
Michaels' natural athleticism was matched only by his ego, and he made the most of every opportunity no matter who stepped up to him.
In particular, he is best known in this time for his rivalry with Bret Hart, but he also played a big role in putting Diesel in a top position.
Yokozuna
Yokozuna was the monster heel of the era that found the most success. He main-evented WrestleMania IX and X while fighting for the WWF Championship.
While he did not have a long run at the top level of the business, this was not a long era, and he was a key player in building up The Hitman.
Owen Hart
In an era of experimentation, Owen Hart hit his opportunities out of the park including an unforgettable rivalry with his brother, Bret.
In many ways, Owen was ahead of his time and never got the opportunities his talent should have provided. Still, his sibling rivalry with Bret is only matched by Michaels'.
Sycho Sid
Few men held the WWF Championship in this era outside of the big stars, but the company did put it on Sycho Sid twice in his rise to prominence.
He was a monster who everyone struggled to fight. He defeated both Bret and Michaels to win the gold and main-evented WrestleMania 13 as champion.
The Attitude Era
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The Attitude Era may always stand as the true of peak of WWE's popularity. This chaotic time was headlined by "Stone Cold" Steve Austin, who was ready to fight anyone.
The top heels were those Austin had to overcome to remain the top man in the business.
Mr. McMahon
There is no more iconic story in WWE than that of McMahon vs. Austin. The working man unafraid to lay out his boss made the most of every opportunity to work with The Boss.
While McMahon could not compete with any of the top faces in the ring, the Attitude Era was far more about what happened outside the ring.
Fans tuned in each week for the chaos that would come from this era, guided by the villainous control of McMahon.
The Rock
While two names defined this era, Austin was always the crowd favorite. The Rock could weave heel and face roles and was not afraid to work with Mr. McMahon and other villains.
Beyond Austin, The Rock also played a key role in elevating Mankind in this time, making him a crowd favorite and a world champion.
Triple H (and Stephanie McMahon)
This is an unofficial dual election as Stephanie was the key to Triple H's rise to top heel status. His takeover of the McMahon family made The Game a problem for everyone in this time.
While he was not able to rise to the level of stardom that Austin and Rock held, he was a strong foil to both men over their careers.
The Undertaker
The rise of The Ministry in the Attitude Era came with much controversy. This dark dominant group, led by The Undertaker, committed some heinous crimes.
They became a constant thorn in the side of Austin and built up The Deadman as a demonic force that could not be contained. Even with the bad corporate alliance twist, Undertaker was a key monster and champion of this era.
The Ruthless Aggression Era
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The Ruthless Aggression Era served a similar role to that of the Next Generation Era. It was a time of shifting tides carried forward by veterans until the new top name arrived.
John Cena would eventually emerge as the one true face of WWE, but he and Batista were both established as the fan favorites at the time with the help of great heels.
Triple H
It could be argued Triple H was the true top star of this era, aided by the dominant support of Evolution.
In this time, he held the World Heavyweight Championship four times while establishing both Randy Orton and Batista as top names in the business.
Even though The Game did not play the key role in Cena's initial rise, he did eventually feud with The GOAT going into WrestleMania 22.
Edge (and Lita)
The rivalry between Cena and Edge rivals even Orton, and they have arguably had more iconic moments, especially when The Rated-R Superstar cashed in the Money in the Bank briefcase for the first time.
Edge naturally shined as a heel, extending to rivalries with The Undertaker, Jeff Hardy and Batista that kept both WWE brands fresh.
Credit also extends to Lita, who was a key factor in Edge's rise. Together, these two may have been the most hated couple in wrestling history.
Randy Orton
While Cena rose to the top of the business as a babyface, Orton became a name to watch as one of the top heels.
He would eventually become a constant problem for Cena, but his primary focus in this era was as The Legend Killer. He went after the biggest name of eras past and put many to rest.
JBL
While Triple H held a firm control of Raw, JBL rose to prominence on SmackDown and became the top man to beat.
While he was only WWE champion once, he did hold the gold for 279 days and put over Cena for his first WWE Championship reign.
JBL would then focus on elevating the next generation of stars as an upper midcard heel with credibility.
The PG Era
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This was the prime era of John Cena, so the greatest heels were defined by their ability to work with him.
The best of the best brought the most of the man that WWE now calls The Greatest of All Time.
Randy Orton
While Orton was a key heel in the Ruthless Aggression Era, he and Cena ran the PG Era. Beyond their constant rivalry, The Viper was often pushing the boundaries of what WWE could allow at this time.
The two never had perfect chemistry, but they became the faces of this era in a similar way to that of "Stone Cold" Steve Austin and The Rock.
Orton was a face and a heel during this era but always just nipping at The GOAT's heels.
Edge
The Rated-R Superstar kept his moniker into the PG Era but was able to quickly acclimate to a new focus. He remained one of WWE's top heels and a constant threat to Cena.
He frequently captured the World Heavyweight Championship, continued his long-running feud with The Undertaker and found many allies to join his cause near the top of the company.
Chris Jericho
While Jericho was a frequent presence in the Attitude and Ruthless Aggression Eras, he did not become a lasting top name until the PG Era.
In particular, his ability to reinvent himself allowed him to find his most serious and dangerous heel persona, particularly delivering one of the era's best feuds with Shawn Michaels.
CM Punk
While Punk's most memorable run in WWE was as a babyface from 2011 to 2012, he still delivered some of the best heel work of the era before and after his breakout.
His Straight Edge Society gimmick and Nexus takeover both gave him fresh and interesting against a variety of rivals, particularly Jeff Hardy, Rey Mysterio and Cena.
His turn on The Rock at Raw 1000 is a legendary moment, even if it was not much longer before Punk decided to retire from wrestling just as a new era began that he had named.
The Reality Era
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The Reality Era was a term coined by CM Punk, but the timeline for this era is set after The Best in the World left the company.
It could more easily be called the Authority Era as Triple H and Stephanie McMahon dominated this period, no matter who was protected by them.
Triple H
No one was more hated in WWE at this time than Triple H, leading to him competing in several huge matches at WrestleMania in an era when he was stepping back as a wrestler.
His match with Daniel Bryan at WrestleMania XXX remains one of the greatest in 'Mania history, setting the stage for The Yes Man's greatest night in WWE.
Stephanie McMahon
This spot could go to Randy Orton as the original chosen man of The Authority, but he danced between heel and face in this era.
Meanwhile, Stephanie McMahon was so hated at this point that Roman Reigns got his biggest pop in this era by spearing her through a table.
While The Billion Dollar Princess was on TV far too often for a non-wrestler, no one could deny she got heat like no one else in this period.
Seth Rollins
The Authority was not a successful concept as a whole, but it did help establish Seth Rollins as one of the top heels of the future.
The Shield's rise is iconic in so many ways for WWE as a whole, but The Architect's turn on his brothers will never be forgotten.
The Heist of the Century is the highlight of this era, allowing Rollins to stand tall at the end of WrestleMania 31 despite not even pinning the current champion.
Brock Lesnar (and Paul Heyman)
The dominance of Brock Lesnar in WWE truly came together in this time as he ended The Undertaker's streak at WrestleMania XXX and went on to become a centerpiece of the world title scene.
His influence was spread out between this era and the next, but The Beast Incarnate never felt more unstoppable than during this era.
It would have never worked without Paul Heyman, though, who elevated Lesnar even when he was not on TV.
The New Era
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So much has changed in the past decade, and WWE will likely redefine this 10 years starting in 2016 by more than one era in the future.
For now, though, it is all defined under a single name, leaving much to discuss on WWE's modern greatest heels.
Roman Reigns
Over 1,316 days, Reigns redefined the business, showing that a top heel could carry the entire company on his back.
It took time for him to find his place at the top, and the title reign ran long many times over, but The Tribal Chief still stands as one of the most iconic heels of this and every era.
Charlotte Flair
Women's wrestling finally arrived in this New Era, and no one better defined the division over these 10 years than Charlotte Flair.
The Queen was the standard-bearer heel every woman tried to take down, and her feud with Sasha Banks changed the business.
She was the driving force behind Becky Lynch's rise to top babyface status and broke every record with her record women's world title reigns.
Daniel Bryan
The most beloved babyface in the business going into WrestleMania XXX became one of the most hated heels heading into WrestleMania 35.
By the end of his time in WWE, Daniel Bryan's heel run arguably surpassed his face work, helping create one of the greatest moments in this era with KofiMania.
Kevin Owens
The journey of Kevin Owens in WWE has mostly been driven by his heel work. While he has not always been at the top, he is frequently making his mark anywhere on the card.
KO's biggest moments include winning the Universal Championship and creating one of the funniest alliances with Chris Jericho. He also was a good enough heel to bring back "Stone Cold" Steve Austin to wrestle one last 'Mania main event.
Owens' legacy has yet to be fully defined as a neck injury has sidelined him indefinitely, but he has still made a lasting mark on the whole of WWE.
