10: Stone Cold Steve Austin

The 2001 heel turn of Stone Cold Steve Austin shocked the world, yet for those loyal watchers of WWE, it may have not come as a surprise. Leading up to his main event showdown with The Rock at WrestleMania 17, Austin would speak time and time again about how he needed to become WWE Champion, and Austin was subtly telling the audience that he would do anything it took to reach the top of WWE once more.

In 1999, before Austin took time away for neck surgery, Austin would become increasingly frustrated with his failures in capturing the WWE Title, and this was when the character change began to take shape. The Austin that was present in WWE in late 1999 was a rattled version of the babyface Austin that fans loved, and an Austin that was slowly but surely losing his way.

9: Ronda Rousey

WWE did the right thing by turning Ronda Rousey heel ahead of her WrestleMania 35 feud with Becky Lynch and Charlotte Flair, and WWE managed to tease the change months before it was official. This tease first came at Survivor Series in 2018, as the crowd for some reason began to turn on Rousey, and during the match, Rousey looked increasingly defeated by the crowd’s response towards her. When Rousey was heckled on the way to the backstage area following her match with Flair, a switch went off in Rousey, as she looked visually distraught, and her character had come to the realisation that these fans no longer cared about her. 

8: Shane McMahon

When Shane McMahon turned heel on The Miz in 2019, it was a truly shocking moment, yet for loyal viewers of the SmackDown product, the teases had been there since 2017.

Names such as Kevin Owens, Sami Zayn, and AJ Styles would claim that McMahon was abusing his power as SmackDown Commissioner, and although McMahon denied this, there was a ton of merit to what these names were saying, as McMahon would often book heels in unfavourable positions. McMahon was often called out by heels for his biases towards them, and due to the fans being conditioned to not question the babyface’s moral compass, the fans naturally sided with McMahon.

When McMahon finally turned heel, these questionable motives and instances of tyranny were brought to the surface, and it was clear that McMahon had been abusing his power for years on SmackDown, and the heels were completely justified in taking issue with McMahon’s antics. 

7: The Rock

The 2002 SummerSlam PPV was main evented by Brock Lesnar overcoming The Rock to become WWE Champion. The match, aside from being excellent from an in-ring perspective, was notable as the crowd noticeably favoured Lesnar in the match.

This would end up being The Rock’s final WWE match until his 2003 heel run as Hollywood Rock, and the interesting thing about Hollywood Rock was that The Great One alluded to the huge change in a post-SummerSlam promo.

Following his loss to Lesnar in the main event of the show, The Rock grabbed a mic, and he looked utterly stunned as the crowd booed and heckled him. The Rock would state that it doesn’t matter if the fans love it or hate it, he was still leaving SummerSlam as the People’s Champion. The Hollywood Rock persona was then heavily teased, as The Rock stated that as of right now, singalong with The Rock is over. The Rock would then exit the ring, and look back towards the audience one more time, as to say that the days of babyface Rock are officially dead and buried. 

6: Triple H

When Triple H failed to defeat John Cena at WrestleMania 22, WWE decided to take his character in a new direction. The Game’s obsession with trying to win the top prize in the company was still present, yet this coincided with a Triple H that was in a moral dilemma, as Vince McMahon was insisting that The Game take out his former friend, Shawn Michaels. What followed was weeks of Triple H mentally reassessing his behaviour, as The Game was presented as being one step ahead of McMahon, as it was clear that Triple H was fully aware that his father-in-law was using him. This hint at a change of character would come full circle, when Triple H joined forces with HBK once again, and the two would rekindle their friendship to take down the evil Mr McMahon.

5: Roman Reigns

Fans rejoiced in 2020 when Roman Reigns joined forces with Paul Heyman as a heel combination. What followed was some of the finest work of both men’s respective careers, and the best thing about the twist of Reigns and Heyman joining up, was that it was teased on WWE TV years prior.

Dating back to 2015, Heyman had always stated how much he respects and personally likes Reigns, and in one 2015 promo, Heyman even stated that Reigns was “the guy”. In terms of Reigns’ more edgier and authentic persona, this began to be teased following WrestleMania 33, when Reigns declared “this is my yard now” after seemingly retiring The Undertaker. 

4: Bray Wyatt

The late, great, Bray Wyatt had lots of strengths as a performer, and one of his more underrated strengths and abilities was his power to tease upcoming gimmicks and characters.

Take for instance, in October of 2015, WWE uploaded a video to their YouTube channel of wrestlers talking about ghost stories, and Wyatt’s video was incredibly captivating.  Wyatt would talk about a mysterious man in the woods, and Wyatt’s description of this man was terrifying, and only years later, it was discovered that Wyatt was talking about the beloved Fiend character. In the video, Wyatt said after seeing the mysterious man, Wyatt sought comfort from Sister Abigail, and this was when Abigail revealed that the mysterious man was Wyatt himself, implying that Wyatt had multiple personalities that could surface at any time.

This was outstanding character work from Wyatt, and the legendary wrestler managed to create an entire universe of characters and lore that will be celebrated for decades to come. 

3: JBL

WWE took a huge risk in 2004, when they decided to give Bradshaw a new gimmick. Bradshaw would turn into JBL and would go from an APA member to a main eventer in the space of a matter of days.

This character change was drastic, yet thanks to strong booking, excellent work from JBL, as well as selfless work from wrestlers such as Eddie Guerrero, the JBL character managed to connect with the audience.

Whilst some fans felt like this change came out of nowhere, JBL’s more money-orientated gimmick was teased the year prior. When JBL released his self-help book regarding finances, this was the first sign that JBL was more than a beer-drinking brawler. JBL’s successes in this world were even referred to on commentary by Michael Cole and Tazz, so it was heavily implied to the audience that a change was coming, and there was much more substance to the former Ministry of Darkness member.

2: Drew McIntyre

One of the wrestlers who was put in an advantageous position following Triple H’s WWE takeover was Drew McIntyre. When McIntyre returned to WWE in the summer of 2023 following a short hiatus, considerable effort was put into McIntyre’s character development.

McIntyre would express logical issues with how he has been treated, and he called out fellow babyfaces for their hypocrisy in welcoming prior members of the villainous Bloodline faction into the locker room with open arms. McIntyre never fully turned against the crowd during this time, and he still firmly kept his morals, and his engagement with the fans was the exact same, despite voicing these issues.

Eventually, McIntyre snapped, and fully embraced his heel side, and although some of his tactics have been underhanded, 99% of McIntyre’s rationale for his actions have been completely justified in every single aspect. 

1: The Undertaker

In 1999, despite The Undertaker’s darker persona being incredibly over with the audience, The Deadman believed that the character had grown stale. A year later in 2000, The Deadman would debut the beloved American Badass persona, yet this persona would be heavily teased on TV before The Undertaker’s extended break in 1999.

Seemingly out of nowhere, The Undertaker would begin to wear regular street clothes both backstage and in the ring for promo segments. The Undertaker’s promo material also became much more authentic, and this was confusing as a viewer at the time, as The Deadman had gone from a demonic cult leader, to a regular badass virtually overnight.

Confusion aside, this was ultimately a smart creative move by WWE, as it allowed the audience to begin to adapt to a new version of The Deadman, meaning that when The American Badass debuted at Judgment Day in 2000, it didn’t come as too much of a significant surprise to the audience.

Fast-forward to the year 2020, and The Undertaker was set to embark in his final ever WWE feud with AJ Styles. Leading up to the match, The Deadman would reference his prior characters, and he would expertly hint that a change was coming. When WrestleMania 36 arrived, these teases would come full circle when The Undertaker rode into his Boneyard match on his trusted motorcycle. This was indeed a new version of The American Badass, yet it had all the prior lore of The Deadman embedded into it. It was yet again wonderful character work from one of the greatest to ever grace a WWE ring.