Top 10 Greatest Heels in Wrestling

Here is my list of the 10 greatest heels of all time in professional wrestling history.

This list has a few older entrants as I seem to be a bit focused on the last 15 or so years. So I thought I would include a few older wrestlers.

No. 10: Harley Race

If wrestling is cyclical, then this guy is the Triple H of the 70’s and 80’s.

Race was a seven-time NWA champion and by all accounts one tough son of a bitch!

Race was way before my time, but the stories of the man still stick in the wrestling industry.

Here is a guy who was a legitimate tough guy, ruling over the NWA as its head honcho and top heel, pre-Ric Flair.

Race’s feud with Flair was what cemented him as one of the all time great bad guys in pro wrestling.

Race was the man who put a bounty on Flair’s head and caused him to “retire” due to the beating he suffered. And yes he was back in about a month, but at this time the whole wrestling world loathed the man.

By 1983 their feud got so intense it had to be settled in a cage, which resulted in the inaugural supercard of Starrcade being created. So for a yearly traditional supercard being invented off the back of such a white hot angle is pretty impressive.

Flair may get the glory for Starrcade ’83, but he was in there with one of the all-time greats in Race.

No. 9: Randy Orton

Whilst right now he is in the stage of anti-hero, no one should forget just how great a heel Orton was as little as one year ago.

2009 was by far Orton’s year; he was in the main event at Wrestlemania 25, won the rumble, and carried the WWE title for most of the summer.

Why did he accomplish so much? Because Orton was just what the WWE had been looking for, a hot heel that could run Raw, as Edge was doing for Smackdown.

The defining moment of his heel turn was during the much-publicized return of Vince McMahon, who was, by default, a face, as he was returning.

Instead of sitting back like every other WWE star, Orton got into Vince’s face and slapped him to the floor, proceeding to punt the chairman right in the head.

Odd how Austin become top face for doing that, but Orton become top heel.

But he didn’t stop there, as Orton then took out every member of the McMahon family—Triple H included.

And I witnessed just how much this guy was hated at Wrestlemania 25. Not one single person on the side I was on cheered for Orton—bar me—and when people saw me cheering, it was like I had cheered on a murderer. It's insane, but shows the guys capability to draw a reaction from the crowd.

Orton may be relatively young and could be on his way to being the anti-hero of the WWE, but this guy was made to be a heel.

If he ever wants to go back to it he could be one of the all time greatest, come the day he hangs up his boots.

No. 8: “Million Dollar Man” Ted Dibiase

There seems to be many types of heel in the wrestling world, but no one seemed to capture greed, arrogance, and just complete jerk as well as Ted Dibiase.

Dibiase is, no doubt, a legend in the business and indeed one of the all time greats, but he sadly never made it to the top.

There were times when Dibiase was fighting Piper for the most entertaining villain in the WWE, but he was never able to get the WWE title from the golden claws of Hogan.

Personally, I feel the moment which will define Dibiase will forever be the basketball challenge. Everyone knows of it, when he challenged a child to bounce a ball something like 20 times, and then, on No. 19, he kicks it away so he doesn’t have to pay the money.

The best part is Dibiase laughing in the kid's face— what a jerk—but made for one hell of a heel.

No. 7: Triple H

In 2000 up until about 2003, there was no better heel in the business than Triple H. Period.

Triple H seemed to evolve throughout his tenure as WWE's top heel. In 1999, he was the new guy looking to make a name for himself, and then by 2001, he was the biggest and best the WWE had.

In 2001 he was malicious and conniving, attributes of some of the best and most ruthless heels have.

It was around that time the nickname “The Cerebral Assassin” was coined, and for good reason. Triple H was the mastermind behind the biggest storyline of 2000, the angle of Austin getting run over.

It may not have worked out as well with Rikishi and the awkwardness of that, but it made Triple H look a million dollars, as he was now the sick deranged star who would do anything to take out his opponents.

In 2003 Triple H went through his Ric Flair phase. Everything bar the robe was there—the stable, the titles, and, most importantly, the lavish lifestyle.

I may be in the minority, but I loved this and thought it was a perfect fit. Triple H owned the Raw main event scene at this time and it just made the WWE audience hate him even more.

Probably the main reason there is a large amount of hatred towards Triple H is because, as everyone knows, he married the boss’s daughter. But like every true star in this business, he ran with it and embraces that hatred, thus evolving his character once again.

When Triple H plays the heel there are very little who can top him. He runs the main event scene and will do anything to stay there, both on and off screen.

No. 6: The Rock

Whilst maybe not automatically associated with the heel role, The Rock was one of the most engaging and charismatic villains of all time.

The Rock may have started off as bubbly good guy, but once they turned him, it was like a light went on in his head and out came this superstar. He went from destined failure to one of the most exciting stars on the show.

Rock’s feuds with Triple H over the IC title were some of the most entertaining hours of TV during the attitude era, mostly due to the Rock.

But it wasn’t until The Rock left the Nation and flirted with a face turn for a while, before taking on his biggest role to date, Corporate Champion, that he truly became a star.

Rock was always flamboyant and cocky, but when he was behind the power of Vince McMahon it was to a whole new level, producing some of the funniest segments of 98-99.

And when Rock found someone to prey on, it resulted in hilarity and genuine excitement.

Mick Foley was the opposite of The Rock—Rock the good looking, athletic, handpicked champion, yet Foley was the everyday man that wanted to be champion.

It was a perfect fit and molded the Rock into a true superstar, as everyone hated, but loved the guy at the same time, helpful when you’re about to become the top face of the company in a year.

The last time the Rock was a heel was back in 2003, and what a way to go out. Rock came back from an extended absence with a chip on his shoulder, and that chip became one of the most captivating characters in WWE at that point.

Rock came back to fight Austin once more, but before he did, he left us with the classic Rock Concerts, something that were both amusing, but made you think “My god what an ass!”

And is that not the pinnacle of what a heel should be, entertaining but infuriating?

No. 5: Hollywood Hulk Hogan

Never has a man be able to fly between good guy and jerk so well.

Hogan was the epitome of the babyface back in the 1980’s and early 90’s, but come Bash at the Beach 1996, and that all changed.

It was the leg drop heard round the world!

Trash was thrown into the ring in disgust; Mean Gene was even hit with a can! All this because of one man, Hulk Hogan. Hogan was turning his back on all his fans and becoming the biggest heel in the business!

No one really knew how well Hogan would be accepted at a Heel, especially Hogan himself. But what was produced was pure gold, literally! What resulted was the nWo, the 80 week lead in the ratings, and WCW becoming the most successful wrestling company on the planet.

Hogan had been responsible for one boom in the 80’s and now he was at the forefront on the next one.

There may not be anyone who ever tops that level of reaction from a heel turn ever again. No one may ever be so versatile to go from top face to top heel so easily and so successfully.

And no one may ever replicate Hogan’s success, but while it lasted, he was one of the most irritating characters on television.

Truly one of the greatest personalities in wrestling history, face or heel.

No. 4: “Rowdy” Roddy Piper

Every good guy has his nemesis, and for Hogan back in the 80’s, that man was Roddy Piper.

With his overblown rock star like attitude and his arrogant manner, it’s easy to see why this guy was one of the biggest stars of the 80’s.

Piper was the most popular and interesting heels the WWE had during Hogan’s run with the WWE title.

Yes Andre was bigger, but what Piper had was vastly more valuable—that being his charisma. Piper was one of the true greats on the microphone. In his heyday Piper could go toe to toe with Flair and Dusty on the mic and still come out looking like gold.

Piper’s classic moments are numerous and legendary. From cracking a coconut over Snuka’s head to being in the main event of the first ever Wrestlemania, Piper has been fundamental in the WWE’s success, and all by playing the bad guy to a tee.

No man in the WWE had really riled up and audience quite like Piper did. He was easy to hate and seemed to love every single minute of it, a true villain of wrestling.

No. 3: Ric Flair

Never has someone made being the bad guy so cool.

Flair was the epitome of indulgence, arrogance, and greed. But this is why we loved him.

Whilst his gimmick was basically a rip off of Nature Boy Buddy Rodgers, Flair took the character and made it into one of the most hated in all of sports entertainment.

Flair, along with the Four Horseman, was one of the most truly hated men in the business during the 80’s. The stories are the stuff of wrestling legend, with the Four Horsemen causing riots in stadiums with their antics.

One of the defining moments was when Flair pretended to be a face and helped out Dusty Rhodes, only to turn on him and have all of the Four Horsemen brutally take apart Rhodes in the ring.

This caused chaos in the arena and all four guys had to be escorted to the back by the riot police, which took 45 minutes.

That is a whole new level of hatred for one single man, a true statement of his ability to rile a crowd.

He was, without a doubt, the greatest heel of the 80’s and he can still get a crowd going today, even though he is a certified legend in the business.

No. 2: “Classy” Freddie Blassie

Freddie Blassie is one of the all-time greats in wrestling history, and possibly the first true superstar of professional wrestling.

No man could touch Blassie in his day.

Blassie’s gift was that he could make anyone hate him, and they did in their millions!

Blassie suffered death threats, 21 stab wounds, and even had acid poured over him at one point in his career. The man wasn’t just the villain, he was the most hated man in wrestling by a country mile in the 50’s.

Freddie Blassie was so hated in the 50’s and 60’s that he became a household name, something that happens only once in a generation in this business.

He was so big that he even declared himself the reason why Regis Philbin had a career, as he made so many appearances on his show at his height of popularity. How many wrestlers can say they made a star out of a non-wrestling personality?

Blassie eventually retired in 1973, but was far from sitting around and enjoying his retirement, as he became one of the greatest managers in pro wrestling.

Blassie managed some of the all-time greats, even Muhammad Ali during his Boxer vs. Wrestler match with Antonio Inoki in 1976.

His career finally ended mid 1980’s, barring numerous appearances on WWE television.

Blassie showed up several times on TV before he died, mainly because he was always on the paid WWE roster for all his loyalty and hard work for the McMahons in the past.

Classy Freddie Blassie died as a true superstar of wrestling and possibly the finest heel ever to lace a pair of boots.

No. 1: Mr. McMahon

Many things happen in this business by accident, but no accident has ever been so rewarding and as entertaining as the character of Mr. McMahon.

For all intents and purposes, Vince McMahon was to stay the announcer for the WWE, and that’s the way it stayed for years.

Until one day, when Bret Hart pushed him on his ass, a new super heel was born to the world.

It wasn’t until the 1997 Survivor Series that the true Mr. McMahon character was shown. It may have been all real backstage, but on TV we were witnessing the birth of a powerhouse in villainy.

McMahon’s defining moment was, by far, his feud with Stone Cold Steve Austin, and to go against the most popular heel in the business you have to up your game immensely.

That’s what McMahon did, and I feel Austin and that storyline wouldn’t have been so successful had it not been for how good a character Vince was for Austin to bounce off of.

Their feud produced some of the most outrageous and captivating moments in pro wrestling.

McMahon may not have been a good wrestler, but he played his part perfectly on screen and accidentally became the biggest heel in all of wrestling at that time.

From 1998 to 2000 there was no more hated man in the business than Vince; he was the political mastermind that tried to stop Austin at every cost.

Without Austin, one would think McMahon would retreat into obscurity, but the reality was far from it, as Vince has been one of the forefront personalities in WWE TV for the last 13 years, showing no signs of stopping.

McMahon’s escapades have been numerous, to say the least. Amongst his rivals are Shawn Michaels, Triple H, Bret Hart, Undertaker, and even God! If a man wages war against God, how can he not be the greatest heel of all time!?

Mr. McMahon may not be the greatest in-ring specialist, but he is, for me, the greatest heel personality that has ever graced the sport of pro wrestling.

No man can top him now, and I doubt anyone will ever again reach the heights of hatred McMahon had during the days of Austin and McMahon.