Heel turns are a great storytelling mechanism within the wrestling business, but they are extremely hard to pull off, particularly in a surprising way. Usually, a change of attitude has been hinted at before the actual turn occurs, which can still be satisfying to watch.
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There are some heel turns that genuinely dumbfounded fans, though, either due to how unlikely they seemed to happen or the brutal way they were delivered. WWE has seen its fair share of heel turns over the years, with some of the best being among the industry’s most memorable moments.
10
Mark Henry (2013)
The Salmon Pink Jacket Fooled Everyone
- Mark Henry had a decent WWE career, which included some world title reigns late in his career
- His best moment came in 2013 when he faked his retirement to target WWE Champion John Cena
- The segment became known as the ‘Pink Jacket Promo’ due to Henry’s disarming choice of attire
Mark Henry by no means had a bad career, as his long tenure in WWE saw him accomplish many things within the industry. However, his best individual performance came very late into his career when he wore a salmon-pink suit jacket to announce his retirement in 2013.
Then WWE Champion John Cena led the crowd in support of ‘The World’s Strongest Man,’ only for Mark Henry to snap on him and lay him out. The fake-out was incredible and immediately re-heated Henry to a main event level, though WWE arguably did not do enough with the future Hall of Famer following the turn.
9
Stephanie McMahon (1999)
Her On-Screen Partnership With Triple H Changed Her Character
- Stephanie McMahon debuted as an on-screen character during ‘The Attitude Era’
- She turned heel by aligning with her real-life husband Triple H in 1999
- Stephanie became known for portraying a heel authority figure throughout her career
At the beginning of ‘The Attitude Era,’ a young Stephanie McMahon portrayed an angelic figure that juxtaposed brilliantly with her evil father, Vince. She was used in many angles, exploiting her vulnerability until WWE flipped the character on its head in 1999 as she seized power alongside her real-life husband Triple H.
Stephanie embraced the overbearing authority figure role that she would go on to play for many years, leaving her innocent past behind.
8
Roman Reigns (2020)
‘The Tribal Chief’ Was A Revelation
- Roman Reigns portrayed a babyface for most of his WWE career, to the resentment of many fans
- He returned after an absence in 2020, turning heel during a match between Bray Wyatt and Braun Strowman
- This would begin his near four-year run as the top heel in the industry as ‘The Tribal Chief’
COVID messed up everything, and wrestling certainly felt the effects of the global pandemic in 2020. WWE was in dire straits operating out of the performance center, but Roman Reigns’ return halfway through the year changed everything.
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The hand-picked babyface star of the previous few years came back as a heel to the shock of the audience, becoming the ‘Tribal Chief.’ The ensuing run saw Reigns lead WWE back into another boom period, all on the back of his shocking heel turn that felt like it would never happen.
7
Shawn Michaels (1992)
HBK Delivered The Dramatic Barbershop Moment
- The Rockers, consisting of Shawn Michaels and Marty Janetty, were a popular team during WWE’s ‘Golden Era’
- The team split towards the end of 1991 amid contract discussion which almost saw them jump to WCW
- Michaels and Jannetty had one final chance at reconciliation during a Barbershop segment in 1992
The Barbershop incident between Shawn Michaels and Marty Jannetty remains one of WWE’s most memorable moments that kickstarted one of the best singles careers of all time for HBK. At the time it was extremely shocking to not only see The Rockers come to blows, but also in such a violent way.
Michaels and Jannetty were on the verge of leaving WWE before the former leveraged the situation to get a heel run, to the ultimate detriment of the latter’s career. Still, the moment served as one of the defining moments in HBK’s career and set the tone for his terrific run leading the company throughout the 1990s.
6
Bayley (2019)
‘The Hugger’ Was Wasted On The Main Roster
- Bayley was highly successful as an earnest babyface on NXT during the mid-2010s
- Her transition to the main roster went poorly as her character was mishandled
- Bayley turned heel in 2019 in a bid to reset her character, which seemed unfathomable to do at one point
During her prime years in NXT, it felt as though Bayley had single-handedly brought earnest babyface wrestling back to WWE. Of course, when she got to the main roster after a lot of anticipation, WWE squandered ‘The Hugger’ by making her seem like a childish, incapable wrestler.
Even so, a heel turn for Bayley felt insane but WWE committed to it in 2019 by having her side with Sasha Banks in her feud with Becky Lynch. Bayley’s shocking turn came with a completely different look and presentation that would help kickstart her main roster career as a heel.
5
Kevin Owens (2014)
KO’s NXT Debut Ended Dramatically
- Kevin Owens made his NXT debut at TakeOver R Evolution, defeating CJ Parker
- His friend Sami Zayn won the NXT Championship after a lengthy pursuit in the main event
- Owens shockingly turned on Zayn following the match, laying the groundwork for their legacy together in WWE
Given their past in Ring of Honor and what has transpired since, it is not all that surprising that Kevin Owens would turn on Sami Zayn shortly after debuting in 2014. However, the manner of the turn was shocking in that Owens decided to ruin Zayn’s big moment by brutalizing his friend after the latter finally won the NXT Championship.
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It was the perfect way to launch Kevin Owens in WWE, doing some of his best work very early on in the company as the top heel in NXT. He has now embraced this side of himself once more after injuring Sami Zayn yet again, a decade after their first spat in WWE.
4
Paul Bearer (1996)
The Undertaker Had To Go At It Alone
- Paul Bearer and The Undertaker’s partnership began in late-1990, shortly after the latter’s debut
- Bearer was essential to Undertaker’s early presentation, as ‘The Deadman’ barely spoke early on
- He turned on Taker in 1996, aligning himself with ‘The Phenom’s’ enemies in Mankind and Goldust
The Undertaker debuted in WWE at the start of the 1990s, beginning one of the most storied careers in wrestling history. None of this could have happened without Paul Bearer by his side during the early years, as the haunting presence both men had together was perfect.
It was weirdly devastating to see Bearer turn on his monster in 1996 to align with Mankind and Goldust, but it made sense shortly after when Kane debuted under the wing of Undertaker’s long-time manager in 1997.
3
Seth Rollins (2014)
‘The Architect’ Destroyed The Shield
- The Shield became the dominant faction within WWE after debuting in late 2012
- Dean Ambrose, Seth Rollins, and Roman Reigns became involved in a feud with Evolution in 2014
- Triple H unveiled ‘Plan B,’ which saw Rollins turn on his brothers, ending The Shield
The Shield were a phenomenon that WWE sorely needed during the 2010s, launching the mainstream careers of three of wrestling’s most important modern stars. Dean Ambrose, Roman Reigns, and Seth Rollins did feel like an unstoppable force, but it was obvious that at some point they would have to go their separate ways.
When Triple H activated ‘Plan B’ in 2014, it was still shocking to see The Shield finally split, especially in the brutal way that Seth Rollins turned on his brothers. It was one of the defining moments of the decade that still gets talked about today for good reason, as Roman Reigns still has not seemed to have forgiven ‘The Architect.’
2
Steve Austin (2001)
‘The Rattlesnake’ Sold His Soul To Mr. McMahon
- ‘Stone Cold’ Steve Austin faced long-time rival The Rock in the main event of WrestleMania 17
- Austin shockingly aligned himself with arch-nemesis Mr. McMahon, who helped him capture the WWE Championship
- WrestleMania 17 is considered to be one of the greatest wrestling shows of all time, in part due to its shocking ending
WrestleMania 17 was a monumental event for many reasons, signifying the end of ‘The Attitude Era.’ Nothing demonstrated this more than the main event, which saw ‘Stone Cold’ Steve Austin shockingly align himself with arch-nemesis Vince McMahon to win the WWE Championship.
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‘The Rattlesnake’ sold his sole to get the world title back one more time, turning heel in what was undoubtedly a mistake looking at the aftermath. Still, it was an unbelievable heel turn that capped off one of wrestling’s all-time great events.
1
John Cena (2025)
It Still Feels Surreal That Cena Is A Heel
- John Cena won the Elimination Chamber, setting up a match with Cody Rhodes at WrestleMania 41
- During the post-match, Cena shockingly turned heel, seemingly aligning himself with The Rock
- This is the first time in his entire career that John Cena has turned heel
Nobody saw this coming, and it still feels unreal to consider that John Cena has turned heel in the final year of his career. Much had been said about what the 16-time World Champion had left to accomplish in his career, but a heel turn seemed completely unfathomable.
Fans still await to see the aftermath of what happened at Elimination Chamber, as John Cena will now face Cody Rhodes for the WWE Championship at his final WrestleMania. It is hard to find a match in wrestling history that has had bigger stakes, which is what the main event of WrestleMania should strive for every year.