WWE history: 10 greatest heel turns of the 21st Century

Three iconic moments that the fans still remember to this day
Three iconic moments that the fans still remember to this day

Over the course of the past several decades, WWE has been consistently producing weekly programming for the WWE Universe, with Monday Night Raw becoming the longest running episodic television show in history.

Wrestling storylines revolve around the basic premise of babyfaces against heels, with the faces coming out on top in most cases to send the fans home happy. On some occasions, a heel turns into a babyface to expand on their character. On the flip side, a babyface sometimes embraces the dark side of their persona and turns into a full-blown heel.

The WWE superstars often have limited control over the creative setup leading to their heel/face switch and are hence required to be versatile enough to capture the imagination of the WWE universe playing both roles.

After taking a peek at 6 greatest babyface turns of the past 20 years, let's take a look at 10 heel turns of the 21st Century that ended up making a huge impact on the business.

These heel turns range from 'did that just happen' to downright shocking.

Also read: 6 greatest babyface turns of the 21st Century

#10 Batista turns on Rey Mysterio

Batista looking at a dazed Mysterio
Batista looking at a dazed Mysterio

At the Bragging Rights 2009 PPV, the world heavyweight title was on the line as The Undertaker, CM Punk, Rey Mysterio and Batista competed in a Fatal Four Way match.

The Phenom ended up winning the whole thing, but that's not what fans remember most about this match.

Also read: 3 shocking ways Triple H vs Batista could end


After the dust was settled, Batista snapped on his longtime friend Rey Mysterio, and proceeded to beat the tar out of him. This kicked off one of the best heel runs of all time, as Batista delivered excellent shoot promos heading into his match against John Cena at WrestleMania 26.

Also read: 5 exciting rivalries WrestleMania 35 could give us

Batista made references to Cena wasting his time kissing babies and hugging girls, while he was preparing to destroy him at The Show of Shows. Batista ended up losing three straight matches to Cena, with the final one being an "I Quit" match. The Animal left the WWE following his rivalry with Cena and went on to build a movie career over at Hollywood.


Also read: 3 times Batista turned on his friends

#9 Triple H turns on Shawn Michaels

Moments before Triple H turned heel
Moments before Triple H turned heel

In the summer of 2002, The Heart Break Kid Shawn Michaels returned to WWE after a 4 year long hiatus.

Michaels convinced his best friend Triple H to move permanently to Monday Night Raw. Weeks before Summerslam 2002, the duo hit the ring to the DX theme on an episode of Raw.

Also read: 5 matches that could steal the show at WrestleMania 35


After the shenanigans were done with, Triple H proceeded to hit a pedigree on Shawn Michaels out of nowhere. As the fans looked in horror, Triple H turned heel on his best friend. The two had possibly their best match till date at SummerSlam, ending with Michaels coming out on top. Triple H hit Michaels with a sledgehammer after the match, which was embraced with a chorus of boos.

Triple H's heel turn resulted in him taking over Monday Night Raw for the next two years, until he was dethroned by his Evolution lackey, Batista, at WrestleMania 21.

Triple H has always looked convincing as the 'apex heel' of the brand and his fabled rivalries include the likes of HBK, John Cena, Goldberg and Kurt Angle.

Also read: 5 huge mistakes that killed WCW

#8 Tomasso Ciampa turns on Johnny Gargano

Ciampa turns heel on Gargano
Ciampa turns heel on Gargano

#DIY was one of the most popular tag teams in the history of NXT. Tomasso Ciampa and Johnny Gargano ran roughshod on the developmental brand's tag team division for a long time.

At TakeOver: Chicago in 2017, Tomasso Ciampa betrayed his former friend Gargano after losing a tag team ladder match to The Authors of Pain. A ruthless beatdown followed as the white-hot Chicago crowd booed Ciampa out of the building.

Also read: WWE Hall of Famer doesn't want to see this NXT Superstar on the main roster


The heel turn resulted in a long-anticipated grudge encounter between the two bitter enemies at TakeOver: New Orleans in 2018. Gargano managed to put Ciampa down after a five-star classic.

Also read: 6 NXT Superstars WWE didn't use correctly

The duo recently joined hands again and were two of several NXT Superstars to jump ship to the main roster. Ciampa tried to attack Gargano again, after failing to advance to the 3rd round of the Dusty Rhodes Tag Team Classic. He didn't succeed this time though, as Gargano sensed this one coming and managed to fend Ciampa off, breaking off #DIY again.


Also read: 5 NXT Superstars WWE used correctly

#7 Shane McMahon turns on The Miz

The duo will battle at WrestleMania
The duo will battle at WrestleMania

Shane O' Mac won the World Cup trophy at WWE Crown Jewel in Saudi Arabia, last year. Following the victory, The Miz began asking Shane to form a tag team with him. The storyline stretched throughout the latter part of 2018, and continued in the new year.

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The duo went on to form a team, beat The Bar for the Tag Team Titles, and lose the belts, all in a very short span of time. Shane and Miz failed to recapture the titles from The Usos at Fastlane. After the match, Shane McMahon turned heel on The Miz in a unique visual. The fans had expected the natural born heel in The Miz to take over his good side again, but the opposite happened.

Also read: 35 iconic images from WrestleMania history

It had been a while since the WWE Universe had seen a heel Shane, and the turn was something fresh and unexpected. They then faced off in a Falls Count Anywhere match at WrestleMania 35, which Shane McMahon won.

Also read: Baron Corbin set to create history at WrestleMania 35

#6 The Rock turns on the people

The Hollywood Rock character in action
The Hollywood Rock character in action

Following his loss to Brock Lesnar at SummerSlam 2002, The Rock left WWE, but came in time for WrestleMania XIX the next year.

This wasn't The Rock fans were expecting to see though. The Hollywood fame had gone to The Great One's head and he came off as an arrogant prick. People didn't care for this version of The Rock and began booing him almost immediately.

Also read: The Rock reacts to fans not identifying him as the first black WWE Champion

The Rock went on to address the fans on an episode of SmackDown, asking them whether he should turn heel. The fans cheered in unison, resulting in the birth of Hollywood Rock, one of the greatest characters in all of wrestling.

Also read: 3 dream matches that could headline WrestleMania 36

Hollywood Rock went on to address the Toronto crowd on an episode of Raw, in one of the greatest promos of all time. The heat Rock garnered that night was something no ordinary WWE superstar could match at their peak.

Also read: 4 dream rivalries we need after WrestleMania 35

#5 Daniel Bryan turns on AJ Styles

The birth of The Planet's Champion
The birth of The Planet's Champion

The Yes Movement in 2014 was one of the hottest storylines of all time, as Daniel Bryan got the kind of cheers icons like The Rock and Austin used to get in their heyday.

After coming back from a supposed career-ending injury, Bryan got into a feud with AJ Styles. The two faced off for AJ's WWE Title at the go home show of SmackDown Live before Survivor Series. During the closing moments of the match, Bryan saw an opportunity open up after the referee got distracted.

Also read: 3 greatest Superstar sendoffs in WWE history


To the shock of the WWE Universe, Bryan hit AJ with a low blow, and proceeded to smash his face with a thunderous knee to the face. This move kicked off the era of The New Daniel Bryan, who cared more about the planet than the people who inhabited it. Bryan created his own customized hemp belt and dropped it to Kofi Kingston at Wrestlemania 35 in one of WWE's most shocking upsets.

Also read: 3 worst Superstar sendoffs in WWE history

#4 Shawn Michaels turns on Hulk Hogan

No one saw this one coming
No one saw this one coming

As SummerSlam 2005 approached, Shawn Michaels and Hulk Hogan faced off against Carlito and Kurt Angle on an episode of Monday Night Raw. After a hard fought match, the duo stood tall in the ring, celebrating together amidst a sea of cheering fans.

Also read: 5 WrestleMania matches Vince changed at the last moment

Out of nowhere, The Heart Break Kid kicked The Immortal Hulk Hogan in the face, knocking him down unconscious. As the fans watched in disgust, Michaels looked at the carnage he had caused and left the ring.

Also read: 8 WWE Superstars Vince couldn't control

The last time Shawn was a heel was way back during his first run in WWE. This came as a complete shocker to everyone. Michaels went on to deliver a scathing promo in Canada and was set to face off against Hogan at Summerslam.


Hogan came out on top in their match at SummerSlam, after which Shawn immediately turned babyface again.

The match is notoriously known for HBK's overselling.

Also read: 7 things WWE should avoid doing at the PPV

#3 Seth Rollins turns on The Shield

The Shield implodes!
The Shield implodes!

The Shield is widely regarded as one of the most dominant factions in the history of wrestling. The trio debuted at Survivor Series 2012, helping CM Punk retain his WWE Title by delivering a triple powerbomb on Ryback.

Also read: 3 reasons we might never see a Shield reunion again


On the Raw after WrestleMania XXX, The Shield turned face by helping Daniel Bryan retain his title against Triple H. For the next several weeks, The Shield feuded with the newly reformed Evolution. The reunion didn't help matters for Triple H, as The Hounds of Justice emerged victorious in their match against Evolution.

Also read: 5 Superstars who should turn heel in 2019


Batista took off to Hollywood again, but Triple H warned The Shield that he had a Plan B.


The Plan B turned out to be Seth Rollins, who betrayed his brothers in a dastardly attack with a chair. Seth Rollins had turned heel and went on to cash in his Money In The Bank briefcase in the main event of WrestleMania 31, winning the WWE title in one of the most shocking moments in WrestleMania history.

Rollins then went on to become the face of the WWE with the backing of the authority.

Also read: 4 Superstars who should turn babyfaces in 2019


#2 Triple H turns on Daniel Bryan

The Game turns heel on Bryan
The Game turns heel on Bryan

By the summer of 2013, Daniel Bryan had become arguably the most popular wrestler in WWE. He was given a shot at John Cena's WWE Title at the SummerSlam 2013 PPV, with Triple H acting as the guest referee.

Also read: 2 legit reasons why the Andre The Giant Memorial Battle Royal should be canceled


After a grueling battle, Daniel Bryan defeated John Cena with a knee to the face. As Bryan celebrated his victory, Randy Orton came down to the ring with the Money In The Bank briefcase in his hands.

Out of the blue, Triple H hit a Pedigree on an unsuspecting Bryan, and Orton pinned him to win the WWE Title. It had been a long while since Triple H had been a heel. This marked the beginning of a year-long journey for Daniel Bryan, with the Yes Movement garnering tons of mainstream coverage. The rivalry came to an end when Daniel Bryan defeated Triple H in the opening match of WrestleMania XXX. He went on to win back his WWE Title by making Batista submit in the main event of the night.

Morel of the story here is to never turn your back on Triple H.

Also read: 5 times Vince McMahon was embarrassed on Live TV

#1 Stone Cold Steve Austin turns on The Rock

Austin turns heel!
Austin turns heel!

The Rock and Stone Cold went toe-to-toe in quite possibly the biggest match of all time, at WrestleMania 17, regarded by many as being the greatest Pay-Per-View of all time.

Also read: 4 things Braun Strowman could do at WrestleMania 35


The duo went on to have a classic in front of 70,000 roaring fans. As the match was about to reach its climax, Mr. McMahon came down to the ring. The boss aided Austin in defeating The Rock, but not before Austin had beaten The People's Champion to a pulp. Several chair shots later, Austin pinned The Rock to finally complete his heel turn.

In one of the most memorable visuals of all time, Austin 'shook hands with Satan himself', as Jim Ross put it.

Also read: 7 Superstars who hurt other wrestlers for real


A week before the match, WWE had bought off its longtime rival WCW. This moment marked the end of the Attitude Era.

Also read: Predicting a 13 match card for WrestleMania 35

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Edited by Atharva Papnoi
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