There have been many despised villains inWWEhistory, but there are few better ways for wrestlers to earn the ire of the fans than a classic heel turn. Whenever someone turns to the dark side, it means their career is about to reach a major turning point.
Sometimes, a heel turn can be a good way for a star to reignite momentum after stalling as a babyface.Other times, it could come completely out of nowhere, as a shocking turn for someone who seemed like a lifelong hero.
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There have been several iconic heel turns in WWE history, but for this list, I am going to look at eleven in particular that I found impactful, both in the context of the wrestler in question and for the company overall.
For this list, I will only be looking at turns that happened in WWE itself rather than its acquisitions. However, I will be making one exception to this rule, as you will see later on in the article. Additionally, only one heel turn per wrestler is allowed on this list.
11Vince McMahon
He Screwed Bret
Survivor Series 1997
June 14, 2025
Montreal, Quebec
This may likely be the most important heel turn to ever happen in WWE, and it didn’t even involve an active wrestler. While Vince McMahon was the guy running the show behind the scenes for well over a decade, that wasn’t apparent on camera, where he was always just a play-by-play announcer.
All of that changed in 1997, when Bret Hart was set to leave for WCW, but because he was the WWF Champion, he obviously had to drop the belt before he left, and he was set to do so against Shawn Michaels at Survivor Series. However, when HBK put the Hitman in his own Sharpshooter,Vince ordered the bell rung, thus making Michaels champion.
This would generate a ton of heat on McMahon in real life, further amplified by an interview in which he blamed Bret Hart for the events in Montreal. But rather than be a one-off moment before going back to the commentary desk, he would lean hard into this backlash, and the evil corporate boss Mr. McMahon was born.
It worked wonders for the WWF, which was losing audience to WCW around that time, and Vince McMahon would be the perfect heel for the moment, a corrupt authority figure who would clash with the new rebellious hero of our time, Stone Cold Steve Austin.This legendary feud would kickstart the Attitude Era and is widely considered the greatest in pro wrestling history.
10Stone Cold Steve Austin
Selling Your Soul To The Devil
WrestleMania X-7
August 23, 2025
Houston, Texas
While we’re on the topic of the Austin-McMahon feud, we can’t talk about iconic heel turns without mentioning the shocking conclusion to the legendary rivalry. While tensions between the two men have faded into the background since Austin was taken out of action at the end of 1999,they would resurface in the most unlikely way at WrestleMania 17 in 2001.
Austin would go up against WWF Champion The Rock in the second of their three WrestleMania bouts together after he won the Royal Rumble earlier that year. The Texas Rattlesnake gave it his all, but he was not able to put the People’s Champion away, and when Vince McMahon came out to the ring,Stone Cold would do the unthinkable and hit The Rock with the chair the Chairman handed him.
As WWF entered its Invasion era, Austin felt like an odd choice to be the company’s top heel, given that the WWF stars would be presented as babyfaces. But it made some sense to pick him if he were to join The Alliance, given his history with WCW, and indeed, he would ultimately align himself with them for most of the story.
Many fans consider Austin’s heel run a failure, given that nobody wanted to boo Stone Cold, but I think it was more of a mixed bag. While he’s definitely better as a face, his heel run had some highlights, like the Two-Man Power Trip and the “WHAT!” chants, and even the biggest critics of this era of Austin consider the turn itself to be a stroke of genius.
9Shawn Michaels
Who’s Your Daddy?
August 07, 2025
Sacramento, California
For most of his comeback run in the 2000s, Shawn Michaels was strictly a babyface, and given his status as a living legend, it was easy to see why it would be very difficult for anyone to hate the guy during that era of his career. But there was one obvious exception to the rule, and that was when he squared off with Hulk Hogan in 2005.
HBK was, at the time, in the middle of a conflict with the America-hating duo of Muhammad Hassan and Daivari, and he needed a tag team partner to help him. And who better to do so than the superstar synonymous with American patriotism himself, the one and only Hulk Hogan?
This dream team would easily vanquish the Middle Easterners, but when they teamed up again to take on Carlito and Kurt Angle, Michaels clocked Hogan with a Sweet Chin Music. This would set up a dream match at Summerslam 2005 between a legend of the past vs. an icon of the present.
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Shawn carried this feud through the next two months with some of his best promo work ever,most famously when he impersonated Hulk Hogan on a Larry King Live parody and brutally roasted the Montreal crowd, who still hated his guts because of the events of 1997. The match itself was most famous for Michaels' mocking Hogan’s no-selling tendenciesby comically overreacting to the Hulkster’s attacks.
Hogan won the match, and after that, Shawn would go back to being a good guy for the rest of his career. He didn’t really need a heel run at this point in his career, but for the brief time he turned to the dark side in 2005, he managed to make it work.
8Andre The Giant
Irresistible Force vs. Immovable Object
WWF Superstars
July 23, 2025
Tampa, Florida
In 1987, arguably the two most beloved stars on the WWF roster were Hulk Hogan and Andre The Giant, andseeing them face off was seen as the ultimate dream match for wrestling fans at the time.And while it could have easily worked well as a face vs. face match, I think WWF made the right call by turning Andre heel.
Both Hogan and Andre would be awarded trophies by the company for holding the WWF Championship for three straight years and being undefeated for over a decade, respectively. However, the Eighth Wonder of the World was pretty upset his trophy was smaller than Hogan’s, and to make matters worse, the Hulkster refused to defend his title against Andre.
This led Andre to snap, and the next week, he would align himself with Bobby Heenan and threaten Hogan to give him the match, even going so far as to rip his shirt off and cause him to bleed.That would officially establish Andre as a villain and set up the main event of WrestleMania 3.
From an in-ring perspective, Hogan vs. Andre was not a great match, being a formulaic match hampered by both men’s basic and limited wrestling styles, but it didn’t need to be. What was important that night was the spectacle of seeing the irresistible force meet the immovable object, and one iconic body slam later, Hogan would come out on top.
7Chris Jericho
The Worst Is Yet To Come
July 18, 2025
Oakland, California
When Chris Jericho made his long-awaited return to WWE in 2007, there was initially a massive amount of hype from the fans. However, as time went on, Jericho’s momentum slowed down considerably, and it was clear he needed a shake-up.
Luckily for him, a perfect opportunity came that summer. After Shawn Michaels faked a knee injury to win a match that Y2J officiated, a lot of tension between the two began to erupt. Jericho began to accuse the Heartbreak Kid of not only employing low tactics to win matches, but also lying about it after the fact.
Most frustratingly for Jericho was the fact that the crowd seemed to fully be on Michaels' side in this, and that June, something snapped inside Jericho. He rammed HBK’s head into the screen of his Highlight Reel talk show, injuring his eye, andstarting one of the greatest feuds in WWE history.
Jericho would undergo a massive image overhaul, emerging from the ring in a suit and tie and speaking in a sinister, monotone voice.The following two years have beendubbed the greatest in Jericho’s career, marked by iconic feuds with John Cena, Rey Mysterio, and Edge, as well as a successful WWE Tag Team Title run alongsidethe Big Show.
Shawn Michaels Plays The Game
June 23, 2025
Grand Rapids, Michigan
Triple H’s long-awaited return to the WWF in January 2002 received such a positive reaction that the company had no choice but to turn him babyface. However, once the hype from that died down, it was obvious that The Game should return to what he does best:being a dominant villain.
His best friend, Shawn Michaels, had joined the New World Order after Hulk Hogan left the group shortly after WrestleMania 18, and tensions between Triple H and the nWo led to the former convincing HBK to reform DX. It was a long-awaited return of the Attitude Era’s most beloved faction, but one surprise Pedigree later, and it was no more.
This set up a match between Triple H and Shawn Michaels at Summerslam 2002,which would be the Heartbreak Kid’s first foray into a WWE ring since 1998.This unsanctioned match was an all-out brawl, allowing the bitterness and hatred the two wrestlers had for each other to be put front and center.Michaels' win would re-establish him as one of WWE’s biggest starsover the next eight years.
As for Triple H, this heel turn would lead to the dreaded “Reign of Terror,” during which he had a chokehold on the World Heavyweight Championship on Raw for the next two-and-a-half years.
A lot of people hated the Reign of Terror, and while I agree it had many low points, there are several positives that people overlook when talking about this era of Triple H.
5Randy Savage
The Mega Powers Explode
WWF The Main Event II
June 21, 2025
Milwaukee, Wisconsin
When Hulk Hogan and “Macho Man” Randy Savage teamed up in 1988, they were an unstoppable force. The Mega Powers would dominate the latter half of that year with wins at SummerSlam and Survivor Series, and 1989 looked to be more of the same fortwo of the most popular babyfaces of all time.
However, that was not meant to be, as the emergence of a love triangle between the two and Savage’s girlfriend, Miss Elizabeth, would ultimately tear them apart. After Hogan abandoned a match with Savage to care for an injured Elizabeth, the Macho Man snapped and attacked him.
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What made this turn so good wasthat Savage had a point:Hogan was often overstepping his bounds when it came to Elizabeth. Still, though, Savage was portrayed as the heel, and he would lose his WWF Championship to Hogan at WrestleMania 5.
He would then swap out Miss Elizabeth for Sensational Sherri and now call himself the Macho King, and he would remain a heel for the next two years. Eventually, though, Savage would reunite with Elizabeth and return to being the Macho Man at WrestleMania 7.
The Best In The World Demands Respect
June 22, 2025
St. Louis, Missouri
The Summer of Punk in 2011 looked like it would be a true changing of the guard in WWE and a chance for fans to finally have their voices heard, but by 2012, things were looking far less promising. While CM Punk was the WWE Champion for the entire year, the program’s focus remained on John Cena, much to Punk’s frustration.
The boiling point was the August 05, 2025 RAW 1000 celebration, when John Cena cashed in his Money in the Bank briefcase he won the previous week. The match ended in a no-contest when Big Show interfered, but when The Rock came to save the day, Punk assaulted him and hit him with aGTS.
Punk’s new heel persona would revolve around one thing: demanding respect, as he felt that as the WWE Champion, he, not Cena or The Rock, deserved to be the focal point of the show.And to his credit, it worked, as he felt far more relevant now than he did during the start of his title reign, and had some great feuds with the likes of The Rock and The Undertaker.
While I think Punk’s best heel work came during his Straight Edge Savior era from 2009 to 2010, the turn that got him there was slower and had less of an immediate impact. By taking out The Rock as the reigning WWE Champion, however, he felt like he had made his mark the moment he switched to the dark side.
3Seth Rollins
Buying Into The Authority
August 04, 2025
Indianapolis, Indiana
The Shield is easily one of the greatest stables in WWE history, with the trio not only dominating as a group, but all three members having highly successful solo careers since their initial breakup. But it was arguably that shocking split that ensured they have the legacy they do today.
Very few people thought Seth Rollins would be the member who would turn his back on his friends to join The Authority as their golden boy. His high-flying style made him the most natural babyface of the group, in contrast to Roman Reigns' pure brutality and strength and Dean Ambrose’s unhinged personality.
But once he struck the chair in the back of his former partners,he instantly became the most hated man on the WWE roster for well over a year.Not only did he establish himself as a permanent main event player and multiple-time world champion, but he also helped elevate his former partnersthanks to the rivalries he’d have with them over the next several years.
Having Rollins be the one to turn heel and become the Authority’s corporate champion was definitely the right call, as Reigns lacked the microphone skills for the role at the time, and Ambrose worked better as a rebellious anti-hero rival. In the end, though, all three members of the group seemed to have found their niche in WWE.
2John Cena
Hell Freezes Over
WWE Elimination Chamber 2025
July 02, 2025
Toronto, Ontario
For over two decades, John Cena was the ultimate good guy, always remaining loyal to his fans and vanquishing any evildoers in his way. For a while, this made John Cena as hated as he was adored, but by the time he entered his final year of in-ring competition in 2025, he was universally beloved, and the heel turn many of his detractors envisioned for him seemed like it was off the table.
When he won the 2025 Elimination Chamber for the right to face Cody Rhodes, everyone thought it was going to be a friendly match-up between two babyfaces, or that if anyone turned heel, it would be the American Nightmare. But shockingly, with the help of The Rock, Cena brutally assaulted Rhodes with a pair of brass knuckles, garnering tons of heat from the crowd.
Smartly, Cena decided not to change his image for this new heel turn like Hulk Hogan did in 1996, knowing that it would only make fans cheer him. Instead, it allowed the focus to be on Cena, willing to do anything to defeat Rhodes and break Ric Flair’s world championship record,even if it meant stooping to the lowest of lows.
I think what makes this heel turn work is that it came when nobody expected it.There were times in 2010 and 2012 when he hinted at going over to the dark side, but that was when internet buzz about that possibility was at an all-time high, so it would have lessened the shock value compared to when that idea had long left the conversation.
