There have been many shocking heel turns in WWE. They spice things up when things are getting a little stale. They enrage fans, they make us feel for the good guys and most importantly, they keep us invested in the stories that are being told.
Now I’ve had to omit Big Show from this list as I have a top 100 Big Show Turns article lined up in the future (just kidding of course). Also not on this list – John Cena. Despite many years of calling for a heel turn, it just never really happened.
There have been many unforgettable heel turns, so buckle up, argue with me about who I’ve missed and who should be higher up, and enjoy the ride!
10. Andre the Giant Turns on Hulk Hogan (1987)
Let’s kick it off with a moment that set the stage for one of the biggest WrestleMania matches of all time. Andre the Giant was everyone’s favourite gentle giant—until he wasn’t. In 1987, after years of being the lovable big man, Andre shockingly aligned himself with Bobby “The Brain” Heenan and challenged his long-time friend Hulk Hogan for the WWF Championship at WrestleMania III.
The betrayal was made even more brutal by the sheer shock factor. Andre, who had been a fan favourite for so long, ripping off Hogan’s shirt and cross was a sight that left fans stunned. This heel turn led to one of the most iconic matches in WWE history, with Hogan body-slamming Andre in front of a packed Silverdome.
9. Evolution turns on Randy Orton (2004)
Randy Orton’s rise to the top was meteoric. As the youngest World Heavyweight Champion in WWE history, Orton seemed destined for greatness. But his success didn’t sit well with his Evolution stablemates, particularly Triple H. The tension within the group reached a boiling point the night after Orton won the World Heavyweight Championship at SummerSlam 2004.
During what was supposed to be a celebration, Triple H gave the infamous thumbs down signal, leading to Orton being brutally attacked by his fellow Evolution members. This heel turn by Evolution, and the subsequent face turn for Orton, was a defining moment in Orton’s career and set the stage for his journey as “The Legend Killer.”
It was a betrayal that left fans in shock and solidified Triple H’s status as one of the most cunning heels in WWE history.
8. Edge Cashes in Money in the Bank on John Cena (2006)
Edge’s heel turn at New Year’s Revolution 2006 was a defining moment in WWE history and solidified him as one of the top villains of his era. Edge had won the first-ever Money in the Bank ladder match at WrestleMania 21, giving him the opportunity to challenge for the WWE Championship at any time of his choosing.
For months, Edge carried the briefcase, waiting for the perfect moment to strike. That moment came after John Cena had just survived a grueling Elimination Chamber match to retain his WWE Championship. Cena was battered, bloody, and barely able to stand when Vince McMahon appeared to announce that Edge was cashing in his Money in the Bank contract.
The crowd was in shock as Edge, who had previously been on the edge (pun intended) of the main event scene, took advantage of a weakened Cena. He delivered two devastating spears and pinned Cena to become WWE Champion for the first time in his career. The suddenness and opportunistic nature of the cash-in were shocking, and it instantly turned Edge into the ultimate heel.
This moment not only marked Edge’s rise to the top of WWE but also set the standard for future Money in the Bank cash-ins. Edge embraced his new persona as “The Rated-R Superstar,” becoming one of the most devious and cunning heels in WWE history. This turn was pivotal in shaping the modern WWE landscape and cemented Edge as a master of playing the bad guy.
7. Seth Rollins Betrays The Shield (2014)
The Shield—Dean Ambrose, Roman Reigns, and Seth Rollins—were one of the most dominant factions in WWE history. They were a brotherhood, a unit that fought for justice and left destruction in their wake. But in 2014, that brotherhood was shattered when Seth Rollins did the unthinkable.
Rollins turned on his Shield brothers by aligning with The Authority and attacking Ambrose and Reigns with a steel chair. This heel turn not only broke the hearts of Shield fans but also catapulted Rollins into the main event scene as one of the top heels in WWE.
There were little mumblings around that someone in the Shield would turn heel, many guessing it may be Ambrose. However, Rollins jumped the gun and broke mine and many others hearts. Still sobbing as we never got a great Shield reunion.
6. Bret Hart Snaps and Turns on America (1997)
Bret “The Hitman” Hart was a beloved hero, a symbol of everything that was good and honourable in wrestling. But in 1997, that all changed in a storyline that blurred the lines between fiction and reality. Frustrated with the direction of the company and feeling betrayed by the fans who were cheering for the rebellious “Stone Cold” Steve Austin, Bret Hart turned heel—not just on a person, but on an entire country.
Hart declared war on the United States, embracing his Canadian roots and criticizing American fans for their lack of morals. This heel turn led to one of the most heated rivalries in WWE history, with Hart leading The Hart Foundation in a cross-border feud that had fans in the U.S. booing him like never before, while Canadian fans treated him like a national hero.
5. Triple H Turns on Shawn Michaels (2002)
The bond between Triple H and Shawn Michaels was legendary. They were the founding members of D-Generation X, the ultimate rebels of the Attitude Era. But in 2002, after Shawn Michaels made his miraculous return to WWE, the unthinkable happened.
During what was supposed to be a heartfelt DX reunion, Triple H shockingly turned on Michaels, delivering a devastating Pedigree. I remember this moment like it was yesterday. I was utterly shocked. I can still hear JR saying ‘HHH has just pedigreed Shawn Michaels straight to hell.‘
HBK’s return to WWE produced many memorable matches and moments (he also makes one of our other Top 10 lists here).
4. Hulk Hogan Joins the nWo (1996)
We all know about Hulk Hogan and how he was a huge babyface during the 80s and 90s. He was the ultimate good guy, the hero who told kids to “say their prayers and eat their vitamins.” But by 1996, Hogan’s all-American persona had grown stale. Enter the New World Order (nWo).
At Bash at the Beach, Hogan shocked the world by turning his back on the fans and joining forces with Scott Hall and Kevin Nash to form the nWo. The red and yellow were gone, replaced by black and white, and Hogan became “Hollywood” Hulk Hogan—the leader of the most infamous faction in wrestling history.
This heel turn not only revitalized Hogan’s career but also changed the wrestling landscape, leading to the hottest period in the history of WCW and the industry as a whole. Who else is humming the NWO theme tune right now?
Eric Bischoff has talked about how Hogan was initially hesitant to turn heel, given that he had been the ultimate babyface (good guy) for over a decade. Hogan was synonymous with the red-and-yellow, all-American hero persona, and turning him heel was a risky move. Bischoff has praised Hogan for having the courage to embrace this new direction, understanding that it was necessary to reinvent his character and stay relevant.
Bischoff also said that Hogan’s heel turn was instrumental in the success of the nWo as a faction. Without Hogan, the nWo might not have reached the same level of impact and cultural relevance.
3. Shawn Michaels Superkicks Marty Jannetty Through the Barber Shop Window (1992)
Before Shawn Michaels was “The Heartbreak Kid,” he was one half of The Rockers, a popular tag team with Marty Jannetty. The two were best friends, partners, and crowd favourites—until Michaels decided it was time to go solo.
In one of the most iconic moments in WWE history, Michaels brutally turned on Jannetty by superkicking him and throwing him through the Barber Shop window during a segment on Brutus Beefcake’s “The Barber Shop” talk show.
This shocking act of betrayal was the birth of Shawn Michaels as we know him today—a cocky, arrogant heel who would go on to become one of the greatest wrestlers of all time. The visual of Jannetty crashing through the glass remains etched in the minds of wrestling fans, symbolizing the end of The Rockers and the beginning of HBK.
2. “Stone Cold” Steve Austin Aligns with Mr. McMahon (2001)
WrestleMania X-Seven is widely regarded as one of the greatest events in WWE history, (and the end of the attitude era) and a big part of that legacy is thanks to the shocking heel turn of “Stone Cold” Steve Austin.
Austin was the anti-hero, the rebellious badass that every fan adored. But at the end of his WrestleMania X-Seven main event against The Rock, Austin did the unthinkable—he shook hands with his arch-nemesis, Mr. McMahon, and effectively sold his soul to the devil.
Austin and McMahon were involved in an incredible feud that lasted a few years. The amount of hatred between these two was there for all to see and the feud brought us many memorable moments. I always loved this feud as it was Austin basically going after his horrible boss and kicking his ass. This, and the fact that WrestleMania took place in Austin’s home state of Texas, made this one a shocker.
Austin grabbed a chair, started to beat the hell out of Rock, pinned him and then shook hands with the devil himself.
1. “Macho Man” Randy Savage Turns on Miss Elizabeth (1991)
In the world of professional wrestling, few moments are as heart-wrenching as the betrayal of a loved one. And no betrayal was more shocking and emotional than when “Macho Man” Randy Savage turned on his manager and real-life wife, Miss Elizabeth.
The Beginning of a Legendary Partnership
Randy Savage (real name Randy Poffo) was already an established star when he introduced Miss Elizabeth (real name Elizabeth Hulette) as his manager in the WWF (now WWE) in 1985. Elizabeth was presented as the perfect contrast to Savage’s intense, unpredictable, and sometimes violent persona. Her calm, elegant demeanor balanced Savage’s wild energy, and together they became one of the most beloved duos in wrestling.
In the storyline, Elizabeth was more than just a manager—she was a symbol of Savage’s softer side. Fans adored her, and Savage’s protectiveness of Elizabeth became a key part of his character. However, this protectiveness often bordered on obsessive jealousy, which would later play a significant role in their storyline.
The Mega Powers and the Explosive Fallout
In 1987, Randy Savage turned babyface (good guy) and formed an alliance with Hulk Hogan, known as the Mega Powers. This partnership was initially a powerhouse, with Hogan and Savage dominating as a tag team. Miss Elizabeth was a central figure in this alliance, managing both men and often being portrayed as the glue that held the Mega Powers together.
However, the seeds of jealousy were planted early on. Savage began to suspect that Hogan was getting too close to Elizabeth, and his insecurities started to drive a wedge between the two. The tension boiled over at The Main Event II in February 1989, when Hogan carried an injured Elizabeth backstage during a match, leaving Savage to fend for himself. After the match, a furious Savage accused Hogan of trying to steal Elizabeth from him, leading to one of the most memorable heel turns in WWE history.
This turn set up the main event for WrestleMania V, titled “The Mega Powers Explode,” where Savage defended his WWF Championship against Hogan. Miss Elizabeth was in a neutral corner, but the tension between the three was palpable. Hogan ultimately won the match and the title, but the storyline had driven a permanent wedge between Savage and Elizabeth on screen.
The Macho Man’s Heel Turn and Breakup
Following the dissolution of the Mega Powers, Savage became increasingly paranoid and abusive toward Elizabeth. He turned fully heel, aligning himself with Sensational Sherri, who became his new manager and on-screen partner. The storyline suggested that Savage had discarded Elizabeth, treating her as if she were no longer important to him.
This period saw Savage at his most villainous, with Elizabeth largely absent from his storylines.
Honourable Mentions
There have been so many memorable heel turns in WWE history that narrowing it down to just ten was no easy task. Here are a few honourable mentions that deserve recognition:
– Chris Jericho Turns on Shawn Michaels (2008)
The rivalry between Jericho and Michaels in 2008 was one for the ages, and it all started with Jericho turning heel by smashing Michaels’ face into a TV screen on the Highlight Reel.
– Paul Bearer Turns on The Undertaker (1996)
The betrayal of The Undertaker by his long-time manager, Paul Bearer, at SummerSlam 1996, was a shocking moment that led to the debut of Kane and one of the most intense feuds in WWE history.
– Edge Turns on Vickie Guerrero (2008)
Edge has had multiple memorable heel turns, but his betrayal of Vickie Guerrero in 2008 was particularly vicious, showing just how ruthless “The Rated-R Superstar” could be.
There we have it. Please let me know who should make this list. I’m sure I will have forgotten a classic and I appreciate you commenting and letting me know! Thank you for reading.
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