Throughout the history of WWE, few actions elicit more disdain from fans than a classic heel turn. This pivotal moment signifies a major shift in a wrestler’s career trajectory, often marking the transition from a fan-favorite to a despised antagonist.
Heel turns can serve as a crucial form of reinvigoration for a wrestler whose momentum has slowed as a babyface. In some instances, these changes come as unexpected twists, shocking fans who have witnessed the individual as a lifelong hero. This article aims to spotlight eleven particularly noteworthy heel turns that have resonated significantly within WWE’s storied legacy.
This list focuses solely on heel turns that took place within WWE, with one notable exception discussed later. Furthermore, to maintain clarity, only one heel turn per wrestler is included.
11 Vince McMahon
He Screwed Bret
| Event | Survivor Series 1997 |
|---|---|
| Date | November 9, 1997 |
| Location | Montreal, Quebec |
This turn arguably stands as the most significant heel turn in WWE history, notable for involving a key executive rather than an in-ring competitor. Vince McMahon, who had been a prominent figure in WWE behind the scenes, took center stage when Bret Hart, the WWF Champion, prepared to depart for WCW.
Hart was scheduled to lose his title to Shawn Michaels at Survivor Series. However, as Michaels locked Hart in the Sharpshooter, McMahon ordered the bell rung prematurely, making Michaels the champion amidst significant controversy. This act generated intense heat for McMahon, who subsequently claimed Hart was to blame.
Rather than retreating back to commentary, McMahon embraced the vitriol directed at him, birthing the character of Mr. McMahon—a corrupt corporate villain. This shift proved crucial for WWF, which was struggling against WCW. The ensuing rivalry between McMahon and Stone Cold Steve Austin ignited the Attitude Era, often regarded as the apex of professional wrestling storytelling.
10 Stone Cold Steve Austin
Selling Your Soul To The Devil
| Event | WrestleMania X-7 |
|---|---|
| Date | April 1, 2001 |
| Location | Houston, Texas |
Continuing the theme of the Austin-McMahon feud, we must highlight the shocking climax of their rivalry during WrestleMania 17. Following a lengthy absence from the ring, tensions flared anew when Steve Austin faced The Rock for the WWF Championship.
Despite delivering a powerful performance, Austin struggled to subdue The Rock. Then, in a plot twist, McMahon appeared ringside, leading to Austin delivering a stunning blow to The Rock using a chair handed to him by McMahon. This unexpected betrayal transformed Austin into one of the top heels of the era, aligning him with McMahon during the Invasion storyline.
While many fans view this heel turn as a misstep for Austin, it introduced memorable moments and rivalries, including the Two-Man Power Trip, cementing Austin’s status in WWE lore.
9 Shawn Michaels
Who’s Your Daddy?
| Event | WWE Raw |
|---|---|
| Date | July 4, 2005 |
| Location | Sacramento, California |
During his comeback run in the 2000s, Shawn Michaels largely maintained a babyface persona, making him revered among fans. However, his dynamic with Hulk Hogan introduced a compelling exception to this trend.
This rivalry was characterized by memorable promos and theatrics, particularly when Michaels mockingly parodied Hogan. Although Hogan triumphed at SummerSlam, this brief heel turn allowed Michaels to explore a darker side of his character.
8 Andre The Giant
Irresistible Force vs. Immovable Object
| Event | WWF Superstars |
|---|---|
| Date | February 7, 1987 |
| Location | Tampa, Florida |
In 1987, the anticipation for a showdown between Andre The Giant and Hulk Hogan reached epic proportions among wrestling fans—two beloved stars finally ready to clash. Rather than risk a face vs.face scenario, WWE opted to turn Andre heel.
Following a trophy ceremony celebrating their victories, Andre, feeling slighted by Hogan’s refusal to defend his title, turned to manager Bobby Heenan and unleashed a brutal attack on Hogan that culminated in ripping his shirt and causing visible bloodshed.
This established Andre as the villain, leading to the iconic match at WrestleMania 3, celebrated more for its spectacle than its in-ring artistry but ultimately a critical milestone in wrestling history.
7 Chris Jericho
The Worst Is Yet To Come
| Event | WWE Raw |
|---|---|
| Date | June 9, 2008 |
| Location | Oakland, California |
Chris Jericho’s long-awaited return to WWE came in 2007 amid much fanfare. However, as his momentum faded, it became clear he needed a revitalizing change.
The perfect opportunity arose when Jericho’s frustrations with Shawn Michaels peaked following an injury caused by HBK. This clash resulted in an explosive encounter where Jericho assaulted Michaels, cementing one of WWE’s most storied rivalries.
This transformation saw Jericho adopt a new appearance and demeanor, setting the stage for what many consider his most monumental and impactful period, marked by top-tier feuds and cinematic storytelling.
6 Triple H
Shawn Michaels Plays The Game
| Event | WWE Raw |
|---|---|
| Date | July 22, 2002 |
| Location | Grand Rapids, Michigan |
After a celebrated return in January 2002, Triple H’s popularity soon began to wane, prompting another turn back to villainy. Initially, he reunited with his old partner Shawn Michaels and attempted to reform D-Generation X. However, one swift Pedigree later, and he shifted gears dramatically.
This betrayal led to a highly anticipated match at SummerSlam 2002, featuring Michaels’ triumphant return to WWE after a prolonged absence. Their unsanctioned encounter, overflowing with emotion and rivalry, showcased both stars’ raw passion.
Triple H’s heel turn set the stage for what fans term his “Reign of Terror, ”a controversial era where he held the World Heavyweight Championship on Raw for an extended duration—not without its share of detractors but also marked by notable matches.
5 Randy Savage
The Mega Powers Explode
| Event | WWF The Main Event II |
|---|---|
| Date | February 3, 1989 |
| Location | Milwaukee, Wisconsin |
The collaboration between Hulk Hogan and Randy Savage, known as The Mega Powers, dominated WWE in 1988. However, a tumultuous love triangle involving Miss Elizabeth would lead to discord in this powerful tag team.
Following a shocking betrayal where Savage attacked Hogan after a match to tend to an injured Elizabeth, he kicked off a transformation into a heel persona once dubbed Macho King. This shift created an intense feud that highlighted the complexities of emotions in wrestling.
Although he would eventually lose the WWF Championship to Hogan at WrestleMania 5, the saga showcased Savage’s character depth, culminating in a successful return to a more heroic role in later years.
4 CM Punk
The Best In The World Demands Respect
| Event | WWE Raw |
|---|---|
| Date | July 23, 2012 |
| Location | St. Louis, Missouri |
The Summer of Punk in 2011 transformed the WWE landscape, but by 2012, frustrations brewed as CM Punk perceived his role overshadowed by John Cena. The tension reached a crescendo during the RAW 1000 celebration, where an altercation with The Rock prompted an aggressive turn by Punk.
Punk’s heel persona emerged as he sought respect amidst the overshadowing narratives. This change allowed him to command attention and grow his character, resulting in riveting feuds with major superstars such as The Rock and Undertaker.
Although some fans had preferred his earlier iterations, this heel turn represented a vital evolution in Punk’s character, positioning him prominently in WWE storytelling.
3 Seth Rollins
Buying Into The Authority
| Event | WWE Raw |
|---|---|
| Date | June 2, 2014 |
| Location | Indianapolis, Indiana |
Recognized as one of WWE’s most celebrated factions, The Shield’s eventual breakup was a pivotal narrative moment. Seth Rollins’ decision to turn on his comrades and ally with The Authority shocked fans and marked a transformative period in his career.
Many saw Rollins as the unlikeliest candidate to betray his team; his high-flying, babyface style starkly contrasted with the other members of The Shield. However, the chair shot to his compatriots instantly solidified his status as the premier heel in WWE.
This heel turn not only provided Rollins with a clear path as a main event player but also kicked off a series of memorable rivalries, ultimately elevating the entire narrative surrounding The Shield.
2 John Cena
Hell Freezes Over
| Event | WWE Elimination Chamber 2025 |
|---|---|
| Date | March 1, 2025 |
| Location | Toronto, Ontario |
For decades, John Cena embodied the archetypal hero, always ready to uplift fans and combat villains in WWE. While this approach garnered him both admiration and disdain, by early 2025, Cena’s character appeared well-established and beloved, rendering the anticipated heel turn unlikely.
After winning the Elimination Chamber, Cena seemed poised for a heroic encounter with Cody Rhodes. However, in a shocking turn of events, Cena brutally attacked Rhodes with brass knuckles, demonstrating a willingness to compromise his values to secure victory.
By resisting a complete character overhaul during his heel turn, Cena managed to keep fans engaged and maintain a focus on his actions rather than a reimagined persona. This unexpected betrayal delivered an impactful spectacle, as many felt shockwaves from a character they believed they knew inside and out.
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