Ranking the 7 greatest heels in WWE history (2024)

A 'heel' in WWE is the antagonist of a story, the bad guy, and there have been some incredibly compelling characters that have appeared on WWE programming over the past few decades. Names such as Mr Perfect and Rick Rude were a huge part of the Rock n Wrestling era of the company in the 80s, being the foil to larger-than-life heroes like Hulk Hogan and The Ultimate Warrior, whereas Triple H and Chris Jericho were the bad guys that stood across the ring from some of the biggest names in the history of pro wrestling like Stone Cold Steve Austin and The Rock.

This list of the Top 5 Heels in WWE history is taken purely from the performer's work in the company itself and the impact that they had on business, so the likes of Ric Flair and 'Hollywood' Hulk Hogan, whilst iconic heels in their own right, did not do their best work in a WWE ring and therefore have been excluded.

7 Triple H

The Game

Training at Killer Kowalski's school in early 1990, Triple H/Paul Levesque would go on to be one of the most influential figures in the history of WWE, both on screen as a villainous heel and off-screen executive.

Starting his WWE (then WWF) career in 1995 as the "Connecticut Blueblood," Hunter Hearst Helmsley would have a slow rise in the company with an over-the-top gimmick that played on stereotypes of well-to-do aristocrats. It was in 1997 that Triple H would solidify himself as a mainstay on WWE programming, joining Shawn Michaels, Chyna and (for a short while) Rick Rude to form D-Generation X. DX was a direct response from the company to WCW's nWo faction, which pushed the envelope on weekly television and tried to adopt a more 'real' approach to the presentation on-screen.

Arguably Triple H's greatest run came in the late 90s/early 2000s, when he adopted the moniker of 'The Game' and became the biggest heel in pro wrestling. Hunter would be the focal point of WWE/WWF programming throughout the year 2000, marrying Stephanie McMahon in the storyline (who he later would go on to wed) and forming the McMahon-Helmsley Regime to run roughshod over the company and essentially 'control' RAW and SmackDown.

Although 'The Game' would go on to be a beloved character in later years, it is his runs at the top of the card as a heel that truly cemented him as a great in the pantheon of WWE.

6 Chris Jericho

First-Ever Undisputed Champion

Chris Jericho has had an extremely long in-ring career with one common thread: the ability to reinvent himself and keep the audience guessing constantly. After debuting with WWE in 1999 after years with WCW, Jericho would instantly make his presence felt by interrupting The Rock on Monday Night RAW and creating arguably one of the greatest moments in the Monday night show's history.

Jericho would continue to be a mainstay throughout the early 2000s, establishing himself as a solid mid-card performer and being a standard bearer for the Intercontinental Championship level. It was in 2002 that Jericho would finally push towards the World Championship level when he defeated both The Rock and Stone Cold Steve Austin on the same night to become the first-ever WWE Undisputed Champion at Vengeance 2001.

Y2J would leave the company in 2005 but make a huge return in 2007, first as a babyface to take on then-WWE Champion Randy Orton but quickly transitioning into the heel role that excels at. Jericho would reinvent his co*cky and brash persona to become more live Javier Bardem's character Anton Chigurh from the 2007 film No Country for Old Men, wearing a suit and speaking with a very slow and deliberate cadence in his feud with Shawn Michaels which remains one of the best from that era.

Jericho would stay with the company until 2018, continually changing his on-screen persona with 'The List of Jericho,' and his feud with CM Punk in 2012 being particular highlights. Easily one of the goats of the modern era of professional wrestling, Jericho's legacy continues to live on.

5 Rick Rude

The Ravishing One

"Ravishing" Rick Rude would make his debut in the WWF as part of the Bobby Heenan Family in 1987, and he would go on to have a ravishing career with the company, becoming an Intercontinental Champion and establishing his legacy as a great of the game.

Although the most critically acclaimed matches of his career would come during his run with WCW, there were still some iconic contests that the former WWE Superstar would be a part of, including his match against The Ultimate Warrior at SummerSlam '89 for the Intercontinental Championship, the Steel Cage match he had against Warrior for the WWF Championship at SummerSlam '90 and his involvement in the Survivor Series '87 alongside Andre The Giant, Butch Reed, King Kong Bundy and One Man Gang.

Rude would establish more of a speaking role later in his career, helping to establish the aforementioned DX in the 90s before jumping back to WCW. Rude would appear on both WWF's Raw Is War and WCW's Monday Nitro on the same night on the 17th November 1997. Because Nitro was live at the time, Rude grew out a moustache for his appearance on Nitro, where proceeded to criticise Vince McMahon, Shawn Michaels, DX, and the WWF.

4 Mr Perfect

Curt Henning

Curt Hennig would start his WWF/WWE career in 1981 till 1983, but it was his return to the company in 1988 as Mr Perfect that truly established him as one of the industry's greatest ever.

His matches against Bret Hart are considered by many to be the best of this tenure, with his SummerSlam 1991 and King of the Ring 1993 contests being the cream of the crop. As an in-ring technician, Hennig was sublime, and he was still able to perform at a high level when he made a return to the company for a short run in 2002.

Hennig's feud with Ric Flair from late 1992 to January '93 also featured a fantastic match between the two men on WWE RAW, elevating his already iconic status and proving that he was able to get back into the ring at the main event stage despite managing Flair earlier that year.

3 CM Punk

The Second City Saint

CM Punk is the most unlikely WWE megastar probably in the history of the company. With his straight-edge lifestyle, smaller frame and lack of athletic background, he didn't appear to fit the mould that WWE would look for in their 'top guy.' This did not deter the former WWE Champion, who would start with the company in the mid-2000s and go on to be one of the biggest stars of the early 2010s, feuding with huge names like John Cena, Triple H and Chris Jericho.

Punk's ability in the ring was only superseded by his gift of gab, as the Chicago native was able to captivate an audience with his promos and sell tickets and PPV buys with his delivery. Starting on television for WWE in ECW, Punk would initially work as a babyface before coming to SmackDown, where he would be unleashed with the 'Summer of Punk,' a storyline that somewhat mirrored his biggest moments in Ring of Honor and cemented him as one of the top antagonists in the industry.

Punk's breakout into mainstream consciousness would come on RAW in 2011 when he would sit on the stage and cut a promo on Cena (who was lying in the ring after losing a match). Punk would blur the lines of kayfabe and reality with his 'Pipebomb' promo, making him the hottest commodity in the industry just a few weeks before his contract was about to run out at the Money in the Bank 2011 event.

The match between Punk and Cena at MITB 2011 is regarded as one of the greatest matches in WWE history, and while Punk was technically a heel heading in, his hometown crowd of Chicago would celebrate him as the returning hero, booing Cena would of the building and creating an iconic atmosphere for one of WWE's best title bouts.

2 Roddy Piper

The Rowdy One

'Rowdy' Roddy Piper is regarded by many as one of the greatest talkers in the history of the pro wrestling business, and his resume as a WWE performer is a testament to that. Piper's in-ring career for the WWF began in 1984 after he started his career there as a manager for the likes of "Dr. D" David Schultz and "Mr. Wonderful" Paul Orndorff.

Piper was pivotal in the creation and implementation of the first-ever WrestleMania event, where he and Orndorff teamed to face Hulk Hogan and Mr T in the main event. WrestleMania needed to be a success, as the company had put everything on the line to produce the massive PPV event, and Piper's work in the build-up by selling to show to potential customers on the microphone ensured that it was a huge hit for the-then WWF.

After a couple of years' break from the company, Piper would return in 1989 and go on to have some of the best matches in his WWF tenure, with his WrestleMania VIII bout with Bret Hart in 1992 being a particular highlight.

1 Mr McMahon

The Boss

As an on-screen character, Mr Mahon can easily be regarded as one of the greatest heels in pro wrestling history, and the former Chairman's persona makes it to the top of this list. Whilst McMahon did not have any blowaway matches during his sporadic in-ring career, his ability to lay the foil to Stone Cold Steve Austin during the Attitude Era of the late 90s changed the landscape of the business and finally allowed WWE/WWF to challenge the industry leaders WCW in the television ratings each week.

Although the plan was never to be seen as the on-screen authority figure, it was the Montreal Screwjob in 1997 that would bring Mr McMahon into the limelight as the owner of the company, with Bret Hart spitting on him after being 'screwed' by Earl Hebner, Shawn Michaels and McMahon himself during his Survivor Series '97 match before he left the company for WCW.

The feud between Austin and McMahon is what really started it all, and that again was out of necessity, as McMahon could not trust that any other talents would stay with the company once they got over with the crowd...but he knew that HE would never leave, so why not put yourself in that position?

Austin and McMahon delivered moments that had never been seen on pro wrestling programming, with the first Stunner on McMahon, the Zamboni and the hospital scene where Austin attacked McMahon with a bedpan all remaining iconic moments in the history of their feud.