10 Amazing Heel Turns That WWE Immediately Ruined

5. Jon Stewart

Dean Ambrose
WWE.com

While not the most conventional wrestling name on this list, the 2015 heel turn from Jon Stewart was not only shocking, but it was immediately made redundant by the simple fact that WWE did zero with it.

Having poked fun at WWE Champion Seth Rollins during a Raw segment in the lead up the Architect's SummerSlam 2015 match with United States Champion John Cena, Stewart surprised the wrestling world by attacking Cena with a chair at the Biggest Party of the Summer.

That chair shot allowed Rollins to pick up the win and take Big Match John's US Title, though there was no actual alignment between Seth and Stewart. Instead, the turn was explained away by a brief segment on the following night's Raw, where the then-Daily Show host said he did what he did so Cena wouldn't break Ric Flair's record of 16 World Championship reigns... which was swiftly followed by an Attitude Adjustment to Stewart as Flair looked on and smiled.

It's not like Jon Stewart was going to have some big run on top as a main event heel or anything, but there was potential here to do something fun with the New Yorker as a short-time antagonist who had others do his bidding.

Instead, all off this was completely forgotten by the time Stewart appeared with the New Day at SummerSlam 2016. Oh, and where was Jon when Cena defeated AJ Styles at the 2017 Royal Rumble to win his record-tying 16th World Title?

Senior Writer
Senior Writer

Once described as the Swiss Army Knife of WhatCulture, Andrew can usually be found writing, editing, or presenting on a wide range of topics. As a lifelong wrestling fan, horror obsessive, and comic book nerd, he's been covering those topics professionally as far back as 2010. In addition to his current WhatCulture role of Senior Content Producer, Andrew previously spent nearly a decade as Online Editor and Lead Writer for the world's longest-running genre publication, Starburst Magazine, and his work has also been featured on BBC, TechRadar, Tom's Guide, WhatToWatch, Sportkskeeda, and various other outlets, in addition to being a Rotten Tomatoes-approved film critic. Between his main day job, his role as the lead panel host of Wales Comic Con, and his gig as a pre-match host for Wrexham AFC games, Andrew has also carried out a hugely varied amount of interviews, from the likes of Robert Englund, Kane Hodder, Adrienne Barbeau, Rob Zombie, Katharine Isabelle, Leigh Whannell, Bruce Campbell, and Tony Todd, to Kevin Smith, Ron Perlman, Elijah Wood, Giancarlo Esposito, Simon Pegg, Charlie Cox, the Russo Brothers, and Brian Blessed, to Kevin Conroy, Paul Dini, Tara Strong, Will Friedle, Burt Ward, Andrea Romano, Frank Miller, and Rob Liefeld, to Bret Hart, Sting, Mick Foley, Ricky Starks, Jamie Hayer, Britt Baker, Eric Bischoff, and William Regal, to Mickey Thomas, Joey Jones, Phil Parkinson, Brian Flynn, Denis Smith, Gary Bennett, Karl Connolly, and Bryan Robson - and that's just the tip of an ever-expanding iceberg. Where his beloved Wrexham AFC is concerned, Andrew is co-host of the Fearless in Devotion podcast, which won the Club Podcast of the Year gong at the 2024 FSA Awards.