Ranking WWE's 25 Most Popular and Beloved Heels of All Time

Erik Beaston@@ErikBeastonFeatured ColumnistOctober 13, 2013

Ranking WWE's 25 Most Popular and Beloved Heels of All Time

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    A heel, according to Merriam-Webster's Dictionary, is defined as "a contemptible person." 

    Throughout WWE history, heels have been essential to telling the stories that have captivated audiences across the globe.

    After all, every hero needs a villain, and the Superstars on this list have been among the most vile in WWE history.

    They have assaulted, degraded, humiliated, bloodied, beaten and bruised babyfaces in WWE rings for nearly five decades and have earned tremendous accolades as a result. Twelve of the 25 stars in these rankings have been inducted into the WWE Hall of Fame, while the remaining 13 are guaranteed a spot at some point in the future.

    Despite their less-than-honorable actions, these heels have earned the adulation and respect of wrestling fans worldwide and, as a result, are among the most beloved and popular performers in WWE history.

    Who are they?

    Find out inside.

    *This article is a look at the most popular and beloved heels ever, NOT the best heels ever. Please keep that in mind.

25. Superstar Billy Graham

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    "I lift barbell plates. I eat T-bone steaks. I'm sweeter than a German chocolate cake. How much more of me can you take?"

    A product of Stu Hart's Dungeon in Calgary, Superstar Billy Graham saw his greatest success in World Wrestling Entertainment come during his second stint with the promotion in 1977.

    Clad in tie-dye t-shirts and tights, sporting bleach blond hair and a chiseled physique, Graham was the epitome of sports entertainment. He was a highly talented talker who borrowed from the legendary boxer Muhammad Ali and crafted his own, unique character that resonated with the fans in Vincent J. McMahon's New York territory. 

    He was the complete opposite of the top star at the the time. Bruno Sammartino was the honorable Superstar who kept his mouth shut and represented the people in every match he wrestled in. He was a champion's champion and carried himself as such.

    Graham was a loudmouth villain who told everyone how great he was. He was flashy and flamboyant. The ultimate showman.

    On April 30, 1977, he defeated Sammartino for the WWE Championship, rolling him up and using the ropes for added leverage. It incensed the fans in Baltimore and set in motion one of the most unexpected title reigns in WWE history.

    It was unheard of for a heel to carry the promotion in those days. If a villain was champion, it was simply to transition the title from one babyface to another. A consummate entertainer, Graham was different. His matches with Sammartino and Dusty Rhodes repeatedly packed Madison Square Garden as fans hoped and prayed they would see someone finally knock him off his perch.

    Eventually Bob Backlund did just that, and suddenly, Graham's run with the promotion was over. He would return throughout the 1980s, but he never quite recaptured the magic that surrounded him in the late '70s and his WWE title reign.

    In 2004, the bombastic star was inducted into the WWE Hall of Fame.

24. Trish Stratus

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    Throughout her Hall of Fame career, Trish Stratus proved on more than one occasion that she could be as devious as she was beautiful.

    As the manager of the tag team T&A (Test and Albert), Trish stopped at nothing to gain the advantage for her guys. During a memorable angle with The Dudley Boyz, she donned lacy lingerie for a handful of vignettes in which she caressed tables in an attempt to play mind games with Bubba Ray Dudley, who had become obsessed with powerbombing her through one.

    When T&A broke up in late 2000, she set her sights on the biggest fish in the WWE sea. She began a torrid affair with Vince McMahon that saw them engage in a make-out session in front of Vince's catatonic wife Linda, all the while earning the scorn of Stephanie McMahon.

    A feud between the two powerful women ensued and climaxed with an outstanding match at the February 2001 pay-per-view No Way Out.

    After being dumped and humiliated by the McMahons on a memorable episode of Raw, she concocted a plan that involved her slapping Vince in the middle of a Street Fight at WrestleMania X-7. From April 1, 2001 until March 14, 2004, she served as wrestling's most popular Diva.

    But that deceitful, cunning side of the multiple-time Women's champion still existed, and at WrestleMania XX, she revealed her true colors.

    For weeks leading up to the event, Trish had been involved in a budding romantic relationship with Chris Jericho. It had torn the friendship between Jericho and Christian apart and resulted in a match between the two at the Showcase of the Immortals.

    Trish would get involved, accidentally (or so it seemed) costing Jericho the match. After the bell, she stunned the fans inside Madison Square Garden by slapping Y2J and revealing that she was actually involved with Captain Charisma the entire time.

    Stratus would become one of wrestling's most entertaining heels throughout 2004, utilizing her sarcastic wit to demean her opponents and her willingness to preserve her Women's title to viciously assault anyone trying to take it away.

    Trish would end her career as a babyface, but her two heel runs are perfect examples of her versatility as a performer and, outside of her gorgeous exterior, a major reason she is remembered so fondly to this day.

    Trish was inducted into the 2013 Hall of Fame prior to this year's WrestleMania 29.

23. John "Bradshaw" Layfield

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    When the calendar switched over from 2003 to 2004, no one would have ever believed that John Layfield, known to fans at that time simply as Bradshaw, would become the centerpiece of the SmackDown brand and the longest-reigning WWE champion in years.

    After all, he had spent the better part of six years as a member of the APA tag team with Faarooq (Ron Simmons), breaking necks and cashing checks. He was an old-school bruiser in the mold of Stan Hansen and Dick Murdoch and had carved out a nice spot for himself in wrestling lore as one of its toughest competitors.

    But the SmackDown brand was devoid of main event talent, and the decision was made to completely change Layfield's character and elevate him to a top spot with the brand. Gone was the beer-drinking badass Texan, and in his place was a loudmouth New York businessman who made millions in the stock exchange and was going to push his world views on the fans of WWE.

    He despised the fact that Mexicans were entering the United States illegally and believed Eddie Guerrero was the epitome of what was wrong with America. He vowed to take the WWE title from him and set everything right.

    After a brutal bloodletting of a match between the two at Judgment Day, JBL made good on his promise and captured the WWE title at the Great American Bash. During his improbable run in '04 and '05, he defeated the likes of Guerrero, Kurt Angle, The Undertaker, Booker T and The Big Show in bouts ranging from Texas Bull Rope matches to Barbed Wire Steel Cage matches.

    He was one consistently entertaining aspect of the SmackDown brand during what many consider the dark days of the brand. He held down the proverbial fort and had the entire then-Thursday night show revolving around him.

    He would lose the title to John Cena at WrestleMania 21 but would not allow that disappointment to derail the momentum he had built for himself the year prior. He continued to serve as one of the biggest heels in the company until he retired from the ring game for good in 2009.

    Today, he spends his Monday and Tuesday nights at the broadcast table, often times sympathizing with WWE's most hated heels.

22. The Honky Tonk Man

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    The Honky Tonk Man was so hated during his time as WWE Intercontinental champion in 1987 and '88 that fans would pack arenas across the country, regardless of the strength of the rest of the card, in hopes of seeing him get beaten.

    The Elvis impersonator was an obnoxious heel who talked about how great he was, all the while "gracing" fans with his supposedly superior singing abilities.

    A less-than-honorable champion, Honky Tonk Man rarely won a match cleanly, instead opting to get himself intentionally counted out or disqualified to preserve his title reign.

    For over a year, the Intercontinental Championship match was booked in the main events of B-level house shows because Vince McMahon knew that the champion was so hated, so despised by the fans that they would show up to watch him get beaten up.

    Honky Tonk Man's run as the centerpiece of WWE's midcard would last until the inaugural SummerSlam event.

    An injury angle saw Ron Bass assault Brutus Beefcake with the spurs on his boot, drawing blood and sidelining the popular star. This left Honky Tonk Man without an opponent. That did not stop him from issuing an open challenge to any Superstar in the locker room to meet him at SummerSlam.

    After all, he had escaped so many matches with his title still in his grasp that he figured he could do it again, not matter who stepped through the curtain.

    Anticipation built throughout Madison Square Garden until the opening riffs of a well-known theme song exploded over the PA system and sent the fans inside the most famous arena in the world into the frenzy.

    The Ultimate Warrior sprinted to the ring and, within a minute, had brought Honky Tonk Man's reign of terror to a definitive end.

    One of the most valuable stars in World Wrestling Entertainment for well over a year, Honky Tonk Man was the rare heel that could carry an entire show thanks to the manner in which he infuriated audiences.

    His induction into the Hall of Fame is long overdue.

21. Kane

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    In the 16 years he has spent with World Wrestling Entertainment, Kane has perpetrated acts of violence on wrestlers and officials that, outside the confines of sports entertainment, would land him in prison.

    Do you recall the time he lit legendary commentator Jim Ross on fire? What about that time he betrayed his brother The Undertaker, locked him in a casket, doused it in gasoline and burnt it with little regard for the human being inside?

    How about when he impregnated Lita and married her in one of the most bizarre wedding ceremonies ever?

    Not enough?

    There was the time he connected jumper cables to the testicles of Shane McMahon and proceeded to electrocute him. Shane's mom Linda did not fare much better. She was the recipient of a Tombstone piledriver on the steel ramp.

    Remember that push Zack Ryder enjoyed late in 2011? Kane killed it.

    With all of the violent, vile and felonious acts he has committed on live television, why does the Big Red Monster remain one of the most popular and beloved characters in WWE?

    For the same reason people became fans of Michael Myers, Jason Voorhees and Freddy Krueger. Kane is the monster we have been afraid of out entire lives comes to life. He is a living, breathing example of evil, and we cannot help but be mesmerized by him and the things he had done.

    Even though comedic angles and losing streaks have watered the character down at points, Kane has always managed to rebound and rediscover the monstrous side that saw him achieve his greatest success.

    Whether he is burying his brother alive or staking after a gorgeous WWE Diva, Kane continues to capture the attention and imaginations of fans across the globe.

20. Mr. Perfect

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    In 1988, WWE began airing vignettes for an incoming Superstar. He would be known as Mr. Perfect and, as the name suggested, everything he did was absolutely perfect. Whether it was shooting basketball, hitting baseballs, high diving, shooting pool or bowling, the cocky new star knew he was great and he had no problem telling you about it.

    From 1988 until 1990, Perfect enjoyed an undefeated streak that quickly established him as one of the elite wrestlers in World Wrestling Entertainment. He defeated the likes of the Blue Blazer, Bret Hart, "Superfly" Jimmy Snuka and The Red Rooster (Terry Taylor).

    His first loss would come at the hands of Brutus "the Barber" Beefcake at WrestleMania VI, but Perfect would rebound nicely, defeating Tito Santana in the finals of an Intercontinental Championship tournament to win the title.

    He would revolutionize the championship, carrying it with a dignity and class that immediately elevated it in the eyes of the fans. His matches with the aforementioned Santana, Kerry Von Erich and the Big Boss Man helped establish him as one of the sport's elite in-ring workers.

    Perfect's strength as one of WWE's top heels was his ability to make his opponents look like world beaters. He would bump around the ring like no other, making a single punch look like he had just been shot at close range. It made it even more impressive, then, when he managed to successfully defend his title.

    At SummerSlam 1991, his final reign with the title came to a glorious end when he fell in defeat to Bret Hart in a match that many consider one of the finest wrestling matches of all time.

    A serious back injury would bring Perfect's in-ring career to a temporary end, but he would remain one of WWE's most talented bad guys. He would second Ric Flair to the ring and assure that he retained the WWE title on a number of occasions.

    In 1995, he returned to WWE and became a heel commentator in the mold of Jesse Ventura and Bobby Heenan. He, like so many that would come after him, represented the company's villains on commentary and helped to get the angles over in a manner that only those who competed in the squared circle could.

    "Mr. Perfect" Curt Hennig passed away in February of 2003. Today, his son Joe carries on the family legacy as Intercontinental champion Curtis Axel.

    Hennig was inducted into the WWE Hall of Fame in 2007.

19. Chris Jericho

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    On August 9, 1999, the Millennium clock ticked down to zero, and Chris Jericho made his eagerly anticipated debut with World Wrestling Entertainment, earning a huge ovation from the fans in Chicago as he interrupted The Rock.

    Jericho would promise all those who listened that WWE would never...EVER...be the same again, and he was right.

    Referring to himself as Y2J, Jericho's initial heel run was a forgettable one, save for one infamous moment. 

    Following an embarrassing loss to female Intercontinental champion Chyna at the 1999 Survivor Series, Jericho bound her to a chair in the backstage area and proceeded to break her thumb with a hammer. It was a moment that contradicted the clever, witty and, at times, comedic heel that Jericho had portrayed up to that point and was deemed to be in bad taste by many.

    Proving to be far too entertaining to be a heel at the time, Jericho became one of the promotion's most beloved babyfaces. For two years, he was one of the marquee stars for WWE, delivering an outstanding in-ring product while proving a knack for combining his humorous side with an intensity that landed him several Intercontinental titles.

    By the time the fall of 2001 arrived, it was clear that Jericho was primed for a main-event run and that he would be turned heel. He began a rivalry with The Rock that produced several Match of the Year candidates and established Jericho as a whiny, obnoxious heel that crowed about how great he was, all the while relying on underhanded tactics to pick up wins.

    As most know, he became the Undisputed WWE champion in December of 2001 at Vengeance and carried the title until WrestleMania X-8, where even an unholy pairing between him and Stephanie McMahon proved unable to keep Triple H from winning the title.

    Jericho would spend three years as a top-shelf heel in WWE, main-eventing pay-per-views and winning championships. His team with Christian during that period was responsible for several memorable moments on Raw.

    In 2008, however, Jericho would experience his greatest success as a heel.

    His feud with Shawn Michaels completely recreated the Y2J character.

    Gone was the sarcastic, witty and the comedic Y2J that fed off of the reaction of the audience. In its place was a colder, more calculating Jericho.

    He called himself the "Best in the World" at what he did and was determined to end his idol, Shawn Michaels. In one of the stiffest, most violent series of matches in recent history, Jericho and Michaels tore each other apart. They beat, bruised and bloodied one another on their way to a phenomenal ladder match at the 2008 No Mercy pay-per-view.

    Jericho would target legendary performers such as Roddy Piper, Ric Flair and Ricky Steamboat as well as Oscar-nominated actor Micky Rourke. He would torment Rey Mysterio and attempt to steal his mask.

    His team with Big Show dominated the tag ranks en route to a WWE Tag Team title reign and three World Heavyweight Championship runs, deserving rewards for the performer.

    Today, Jericho is an enormously popular star regardless of whether he is a heel or hero, full-time or part-time competitor.

18. Edge

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    From 2005 until 2010, there was no more vile, despicable villain on the WWE roster than the "Rated R Superstar," Edge.

    His obsession with becoming World Heavyweight or WWE champion resulted in his heel turn after years of serving as a very popular babyface, but his real-life affair with Lita and the ensuing angle that resulted established him as the most hated man in sports entertainment.

    In the summer of 2005, Matt Hardy returned to WWE and engaged in a brutal, emotional angle with Edge that saw the two Superstars beat the unholy hell out of each other. There was no ring nor was there any type of gimmick match that could contain the hatred they had for one another, and that definitely came across on television.

    Ultimately, Edge would win the rivalry, shipping Hardy off to the SmackDown brand while he continued his climb up the ranks on Raw.

    On January 9, 2006, Edge cashed in the Money in the Bank contract he had won back at WrestleMania 21 and captured his first WWE Championship by defeating John Cena. His first title reign would come to a premature end after a few weeks, but if the ratings for Raw at the time were any indication, fans were intrigued by the, pardon the pun, edgy new main-event star.

    Edge would have an outstanding Match of the Year candidate against Mick Foley at WrestleMania 22 and gained a ton of momentum throughout the spring and summer. By July Fourth weekend, he was once again WWE champion and was in the midst of a career-defining rivalry with Cena.

    From 2007 until 2009, Edge was the top heel on the SmackDown brand, the centerpiece around which nearly every story revolved. His relationship with general manager Vickie Guerrero made him look like the sneaky, despicable villain he was, and rivalries with Undertaker and Batista over the World Heavyweight Championship proved that he was a performer capable of handling the pressure that comes along with a main event push.

    Whether it was the legendary five-second poses with Christian in 2000, Live Sex Celebrations with Lita or manipulating on-screen wife Vickie Guerrero into making decisions that best suited him, Edge stopped at nothing to keep his spot as a top dog in WWE.

    His antics made for interesting and entertaining television, while his incredibly intelligent in-ring work established him as one of the great workers of his generation.

    Unfortunately, a serious neck injury prematurely ended his career in 2011.

    He was inducted into the WWE Hall of Fame the following year.

17. Jerry "the King" Lawler

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    A legend in his hometown of Memphis, Jerry Lawler's arrival in World Wrestling Entertainment in late 1992 had plenty of concerns. After years of booking his own promotion, would he be willing to take orders from someone else? How would he be accepted by a locker room full of wrestlers that worked for him and may or may not have been shorted in pay?

    While it was anything but easy for Lawler behind the scenes, he thrived as the antagonist of Bret Hart.

    Lawler was brilliant in his insults of Hart's parents Helen and Stu. As a broadcaster and the host of The King's Court talk show, he would never pass up the opportunity to poke fun at their age or the number of kids they had.

    He used the insults to get underneath the skin of Hart, but it was his physical assault of the former WWE champion that took the angle to another level.

    Hart won the 1993 King of the Ring tournament after defeating Razor Ramon, Mr. Perfect and Bam Bam Bigelow in one night. As he stood victoriously, a crowd on his head and a robe draped over his shoulders, Jerry Lawler appeared. He was infuriated that Hart would dare call himself the king when it was he who was the real king of wrestling.

    Lawler attacked Hart, breaking a scepter over him and leaving him lying to close out the show.

    The feud would culminate, for the first time, at SummerSlam. Lawler would claim injuries suffered in a car accident would keep him out of the match against Hart so he found a suitable replacement in the form of Doink the Clown.

    Hart dismantled Doink, forcing him to tap out to the Sharpshooter.

    Lawler, dismayed, attacked Hart with a crutch. It was then announced that Lawler was fine and that the scheduled match between him and Hart would go on. Eventually, Hart would lock in his trademark submission hold for a second time and score the win.

    His refusal to break the hold, however, resulted in a reversed decision and win for the dastardly Lawler!

    Over the next two years, Lawler would find himself involved in Bret's affairs. They would compete in a Kiss My Foot match at the King of the Ring 1995 pay-per-view, which would lead to the introduction of Lawler's Big Red Dentist, Isaac Yankem.

    From there, Lawler would become a permanent member of the Raw broadcast team and build a reputation for himself as one of the voices of the Attitude Era. Whether it was defending the actions of his son Brian Christopher and the other rule breakers in WWE or calling for the many voluptuous Divas to show off their puppies, Lawler proved always entertaining.

    Still part of the Monday Night Raw broadcast team to this day, Lawler is far more popular now than he was some 20 years ago.

    In 2007, his work as an in-ring competitor, personality and commentator earned him a spot in the WWE Hall of Fame.

16. Paul Heyman

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    The leader of the ECW Revolution and one of the most gifted bookers and talkers in wrestling history, Paul Heyman has a very limited resume with Vince McMahon's company but remains one of the most popular heels in WWE's long and illustrious history.

    In 1997, Heyman led a small invasion of ECW stars on Monday Night Raw. It was a promotional tactic that netted the upstart Philadelphia-based wrestling company new viewers and a healthy buyrate for its inaugural pay-per-view event.

    It would be the final time the owner of Extreme Championship Wrestling appeared on WWE programming until 2001.

    That year, ECW closed its doors, and Heyman sought employment elsewhere. With the offer to fill the vacancy Jerry Lawler's departure from WWE left on the table, Heyman joined Jim Ross at the announcers table and quickly established a chemistry with the legendary broadcaster that resulted in one of the more underrated announcing teams the company had seen.

    It was only a matter of time, however, before Heyman reverted back to his days as a loudmouthed heel in WCW and various wrestling territories. 

    On July 9, 2001, Heyman rose from his announcer's position and joined former ECW Superstars in the middle of the ring and revealed to the world that he and his guys would be the second company to invade WWE that summer.

    Later that same night, the ECW wrestlers would join WCW wrestlers in an unholy alliance. Heyman stood shoulder-to-shoulder with Stephanie and Shane McMahon and reveled in the idea that they could orchestrate a hostile takeover of WWE.

    The WCW/ECW invasion ultimately failed, and Heyman was left with nothing to do.

    That is, until the a once-in-a-lifetime prospect was about to make his WWE debut.

    The night after WrestleMania X-8, Paul Heyman reappeared on WWE television, this time at the side of the beat incarnate, Brock Lesnar. The massive, athletically gifted Superstar would tear through WWE's top stars, including the Hardy Boyz, Ric Flair, Rob Van Dam, Hulk Hogan and The Rock before capturing the WWE Championship.

    Heyman would guide Lesnar's career during his early days with the company and manage him to a huge Hell in a Cell victory over Undertaker at No Mercy 2002.

    After splitting from Lesnar and suffering a beatdown at the hands of his former client on SmackDown in early 2003, Heyman would disappear from WWE television, reappearing briefly in 2004 as the brand's general manager.

    In 2012, Heyman would return to WWE and immediately partner with WWE champion CM Punk. The former ECW owner would be by Punk's side as he enjoyed a monumental 434-day reign. It was the longest reign in 25 years and a major accomplishment considering the ever-changing landscape of sports-entertainment in the 21st century.

    Today, Heyman manages both Curtis Axel and Ryback and has been engaged in a rivalry with Punk for the last four months.

15. Shawn Michaels

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    On December 2, 1991, Shawn Michaels tossed longtime tag team partner Marty Jannetty through a glass window on the Barber Shop talk show segment, setting in motion events that would lead to him one day being referred to as the greatest professional wrestler ever.

    Dubbed "The Heartbreak Kid," Shawn Michaels referred to himself as God's gift to women. With Sensational Sherri guiding him through the first year of his singles career, he captured the Intercontinental Championship and challenged Bret Hart for the WWE title in the main event of the 1992 Survivor Series.

    He suffered a setback in 1993 when a failed drug test earned him a suspension. When he returned, he took exception to the fact that Razor Ramon was recognized as Intercontinental champion despite him never losing the title.

    At WrestleMania X, they would compete in a ladder match that would set the standard for every one that followed. Ramon won the match, but it was Michaels who caught the eye of management and earned himself a main event push, culminating in a loss to WWE champion at WrestleMania XI.

    In 1997, Michaels would once again assume the role of heel after carrying WWE as its top babyface for most of 1996.

    A degenerate of the highest order, the Heartbreak Kid bonded with Hunter Hearst Helmsley, and the two of them formed D-Generation X, the revolutionary faction that introduced a certain attitude to WWE that it had been missing before.

    Michaels' rivalry with The Undertaker during this period resulted in one of the most barbaric matches in the history of the promotion, that being the inaugural Hell in a Cell match at the October 1997 Badd Blood pay-per-view.

    The man who oftentimes referred to himself as the Showstopper, the Icon and the Main Event was dismantled by the Dead Man, beaten from one side of the cage to the other and bloodied, but thanks to the debuting Kane, still scored a win over his heated rival.

    Michaels' involvement in the Montreal Screwjob made him one of the most hated men in the industry both on camera and behind the scenes.

    At WrestleMania XIV, his reign as WWE champion and top baddie in the industry came to an end at the hands of Steve Austin.

    He would never again return to playing a full-time heel. He did, however, stir the pot in the weeks leading into his battle with Hulk Hogan at SummerSlam 2005. He made sarcastic shoot comments regarding Hogan and spent a lot of time poking fun at the Hulkster's age. It would all be for naught as he returned to his honorable ways the night after big match.

    In 2011, Michaels took his rightful place among the industry's greatest as he was inducted into the WWE Hall of Fame.

14. Kurt Angle

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    A legitimate Olympic gold medalist for the United States in the 1996 Olympic Games, Kurt Angle debuted in November of 1999 with a lot of hype surrounding him.

    Video vignettes leading up to the Survivor Series featured Angle listing his many accomplishments.

    In a different era, he would have been an American hero, a potential main event babyface. But in the Attitude Era in which he performed, he was a cookie-eating, milk-drinking goody-two-shoes whom fans simply could not relate to.

    He was booed from the minute his music hit and he entered the arena for the first time. Incensed by the lack of respect he received from the crowd, he would exit the squared circle and grab a microphone at ringside.

    "How dare you boo me. I'm an Olympic gold medalist," he would remind them. It only helped to incite a louder, more negative reaction from the people, making him one of the most despised stars of the era.

    As hated as he was, however, he was equally as talented and skilled between the ropes. A natural in terms of in-ring ability, he quickly became one of the top workers in a company full of them. Matches with Chris Jericho, Chris Benoit, Eddie Guerrero, The Rock and Triple H established him as one of wrestling's elite.

    In the summer of 2000, his infatuation with the very married Stephanie McMahon-Helmsley led to an interesting and entertaining feud with Triple H. Despite coming out on the losing end of a one-on-one battle with The Game at Unforgiven in September, he got the last laugh by defeating The Rock for his first WWE title a month later.

    Angle always demonstrated a comedic side, but the backstage vignettes shot with Steve Austin and Vince McMahon in the summer were gems.

    Throughout his career, Angle proved his ability to play both the hero and the villain, but his greatest work came when he was breaking the rules and punishing the top good guys in the sport with his intense in-ring style and bone-shattering ankle lock.

    Angle would leave WWE in 2006 and use his star power to attract viewers to TNA Wrestling.

    His fans hope that, before his career comes to an end, he returns to the company that made him famous.

13. "Million Dollar Man" Ted DiBiase

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    "Everyone has a price!"

    Or so Ted DiBiase told the world every time he appeared on WWE programming.

    In several vignettes to promote his impending debut, the former Mid-South Wrestling star would prove his point. Whether it was convincing a lifeguard to clear the pool so he could have it to himself or paying off a host to get him a table at a restaurant before dozens of others waiting in line, DiBiase demonstrated that anything he wanted, he could get for the right sum of money.

    What he really wanted was Hulk Hogan's WWE Championship. When Hogan refused his offer, DiBiase enlisted the services of Andre the Giant. In a highly controversial match on network television, Andre defeated Hogan for the title and promptly sold it to DiBiase.

    The transaction was deemed illegal by WWE President Jack Tunney, and the title was vacated (take that, abeyance).

    DiBiase would compete in the finals of the championship tournament at WrestleMania but would fall to "Macho Man" Randy Savage, thanks to some assistance from Hogan.

    The Million Dollar Man would enjoy success as one of the company's top stars throughout the '80s. He teamed with Andre in a losing effort against Savage and Hogan at the inaugural SummerSlam event, and his feuds with Jake Roberts, Brutus Beefcake and the Ultimate Warrior helped make him a household name.

    In 1990, his feud with Dusty Rhodes introduced fans across the world to the American Dream's son Dustin, a good-looking, talented young man who would go on to great success later in the decade as Goldust.

    After years of mistreating him, DiBiase was stunned when Virgil stood up to him. Their rivalry culminated at SummerSlam 1991 when the former assistant defeated his boss and captured the Million Dollar Championship.

    A partnership with Irwin R. Schyster, dubbed Money, Inc., would net DiBiase three different reigns as WWE Tag Team champion. Their match against Hogan and Beefcake at WrestleMania IX was dubbed as one part of a double main event.

    Injuries forced DiBiase to retire from active in-ring competition in 1993, but the second-generation star remained busy in WWE. He built a stable known as the Million Dollar Corporation and guided stars such as Tatanka, Bam Bam Bigelow and the supreme fighting machine Kama to varied levels of success.

    DiBiase departed from WWE in 1996.

    In 2010, he was inducted into WWE's Hall of Fame.

12. Triple H

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    Whether it was as the Connecticut blue blood Hunter Hearst Helmsley, the degenerate co-founder of DX, the Cerebral Assassin, the leader of Evolution or the King of Kings, Triple H has established himself as one of the great heels in wrestling history.

    As Helmsley, his rivalry with Godwinn was more fun than serious and culminated with a Hogpen Match at In Your House V in December of 1995. The snobby competitor picked up the win but was humiliated when Godwinn back-body-dropped him into the pen. The sight of Helmsley rolling around the slop and pig excrement paid off the angle.

    In 1997, his rivalry with Mankind evolved his character. For the first time in his career, he showed an intensity and aggression that hinted that he may be capable of so much more if given the opportunity.

    That opportunity came when he and Shawn Michaels formed D-Generation X. Suddenly, a performer who was stuck jerking the curtain at house shows a year earlier was a top heel for the company as it entered the hottest and most successful period in its history.

    After a year-long run as one of the most popular stars in the industry, Triple H would turn heel in 1999 and experience the first main event singles push of his career.

    In a famous shoot promo from Sunday Night Heat leading into SummerSlam, Triple H voiced his frustrations with different events from his career and said it was his time.

    On the Raw following the summertime spectacular, Triple H accomplished a childhood dream by capturing his first WWE Championship.

    Two months later, he would interrupt the wedding between Stephanie McMahon and Test and reveal that he had married Stephanie the night before. It was a major step in establishing the despicable nature of The Game and the lengths he would go to in order to come out of a conflict on the winning end.

    At Armageddon in December of '99, Stephanie would reveal that she was a willing participant in Triple H's plan, and the critically acclaimed McMahon-Helmsley Era would kick into the effect on the following night's Raw.

    Throughout 2000, Triple H was WWE's unquestioned MVP. He was the most hated wrestler on the planet, but he was also responsible for a long line of Match of the Year candidates.

    Unfortunately, a quadriceps injury in 2001 would sideline him and prevent him from continuing his unmatched streak of quality bouts.

    From 2002 until 2006, Triple H would dominate WWE in what his harshest critics refer to as "the Reign of Terror." He was always in the main event, almost always the World Heavyweight champion and rarely lost clean to anyone.

    In 2013, Triple H assumed the role of authority figure and set about shaping the company in his vision. Daniel Bryan as WWE champion is not in his vision, and he has done everything in his power since SummerSlam to prevent that from happening.

    Despite his role as the top heel in WWE, Triple H still receives a thunderous ovation when he enters arenas.

11. The Rock

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    Sports entertainment's most electrifying Superstar rebounded from a horrendous babyface push early in his career to become one of the most hated stars on the roster by the summer of 1998.

    The leader of the Nation of Domination, The Rock had no problem insulting the audience that turned its back on him. He spouted off catchphrases and, whether those in the crowd liked him or not, became one of the most entertaining performers on the roster.

    The Nation's rivalry with D-Generation X resulted in an angle involving Rock and Triple H that allowed both to break out in one of WWE's most prominent feuds of the Attitude Era.

    At SummerSlam in August of 1998, Rock and Triple H did battle in a ladder match for the Intercontinental Championship that, while won by the leader of DX, catapulted The Great One into the upper tier of WWE Superstars.

    Three months later, at the Survivor Series, Rock would capture the WWE title after defeating Mankind in the finals of a tournament. He would be revealed as Vince McMahon's handpicked corporate champion and would represent the chairman in his wars with Stone Cold Steve Austin and Mankind.

    The "I Quit" match between Rock and Mankind at January 1999's Royal Rumble saw the third-generation star deliver no less than 12 unprotected chair shots to the head of his opponent, proving he had a ruthless, dangerous side to him few knew existed.

    Despite his role as a heel, Rock's penchant for entertaining the crowd with humorous one-liners and catchphrases made him a favorite of WWE fans.

    After losing the WWE title to Austin WrestleMania XV, as well as the subsequent rematch at Backlash, Rock would become one of the biggest babyface stars in the history of World Wrestling Entertainment.

    He crossed over into mainstream media and had several movie roles lined up.

    Between 2001 and 2002, he appeared sporadically. By the time he competed against Brock Lesnar at SummerSlam in August of '02, fans were tired of his wavering allegiances. If Rock would not choose between his burgeoning Hollywood career and his established wrestling career, they would choose not to support him.

    When Rock returned in 2003, he used the jeers of the fans to craft a new character. He was no longer the People's Champion. Instead, he was the Hollywood movie star who made the pedestrian lives of WWE's fans that much better by gracing them with his presence. He was above them now.

    At WrestleMania XIX, the greatest rivalry in WWE history came to an end when Rock defeated Steve Austin for the first time in three attempts. After putting the incoming Goldberg over at the following month's Backlash pay-per-view, he disappeared again from WWE programming.

    The Rock's run in 2003 would be the last time he would portray a heel in WWE.

    Though he is remembered for his days as one of the most popular babyfaces in wrestling history, his two stints as a heel provided fans with some of his finest work. 

10. The Undertaker

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    Debuting at the 1990 Survivor Series pay-per-view, The Undertaker would go on to become the phenom of World Wrestling Entertainment and the most respected Superstar to ever grace its rings.

    Led to the ring by the legendary manager Paul Bearer, Undertaker terrorized wrestlers and fans alike with his methodical pace and his punishing offense. His trademark Tombstone piledriver downed many top Superstars during his early days with the company, including his first WrestleMania casualty, Jimmy Snuka.

    Just one year after entering the company, he would receive his first heavyweight title shot.

    The Dead Man would make the most of it, capitalizing on interference from Ric Flair to win the WWE Championship. His reign would be limited, as would his time as a heel. By 1992, he was one of the top babyface stars on the WWE roster.

    In 1998, at the height of the Attitude Era that revolutionized pro wrestling and set box office records, The Undertaker would undergo a character makeover that would push the limits of what would be acceptable television.

    In December of that year, he and Paul Bearer abducted Steve Austin and attempted to embalm the living, breathing star of the company. Kane would prevent that, but the Dead Man was just getting warmed up.

    In 1999, he would reappear as the leader of his Ministry of Darkness. Gathering a collection of midcard talents to serve under him, he put the entire WWE on notice. He threatened the family of owner Vince McMahon and made a habit of "sacrificing" Superstars by hanging them on his giant "T" symbol.

    The lovely Ryan Shamrock would be one of those sacrificed persons while Stephanie McMahon was strapped to the logo for a black wedding that was, thankfully, broken up by Steve Austin.

    It would later be revealed that Undertaker and Mr. McMahon were working together to assure the destruction of Steve Austin, and by September of '99, the Phenom had mysteriously disappeared from television.

    He would not return to his villainous ways until late 2001, when he became the biggest bully in WWE. He forced Jim Ross to, literally, kiss McMahon's backside and tormented the likes of Rob Van Dam, Jeff Hardy, Ric Flair and Hulk Hogan en route to another WWE Championship reign.

    Eventually, however, a lack of box office draws on the babyface side of the roster resulted in another run as one of the company's reliable good guys by the time August of 2002 rolled around.

    He has been a babyface ever since.

9. Bobby "the Brain" Heenan

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    Bobby Heenan is the greatest manager in wrestling history.

    Bar none.

    And during the height of the wrestling boom in the mid-to-late '80s, Heenan starred for World Wrestling Entertainment as one of its biggest, brightest personalities.

    Throughout the decade, managers played a pivotal role on WWE programming. They were the spokespeople for those Superstars who lacked promo skills and were important pieces in storylines.

    With so many managers taking up television time, there was a certain pecking order among them. Heenan was at the very top of that order. He was the manager in charge of the most relevant main event stars.

    He guided men such as Big John Studd, Andre the Giant, King Kong Bundy and Rick Rude to championship bouts and had his fair share of run-ins with industry icon Hulk Hogan.

    Everyone he ever managed was better off for having been under the tutelage of Heenan.

    On the occasions when a big match between Hogan or Ultimate Warrior and one of his guys would need to end without the heel looking weak, Heenan would enter the ring and take a series of big bumps to send the crowd home happy.

    He had such a mind for the business and the performance aspect of it that anyone who ever watched him ply his craft instantly knew he was head and shoulders above just about anyone else on the card.

    Heenan excelled in other aspects of the business as well.

    As the host of Prime Time Wrestling, he and Gorilla Monsoon updated fans on the top stories in WWE and introduced the matches on that week's show. Their back-and-forth quips and banters made for entertaining programming that fans of that era still hold in great regard.

    Heenan and Monsoon's work as commentators, however, is remembered even more fondly.

    For an example of how great they were together, one needs to look no further than WrestleMania VIII. The arguing between them, the way Heenan constantly defends Ric Flair and wishes ill towards Hogan while Monsoon tells him off is a joy to listen to. They manage to make the worst matches on the card more entertaining.

    Heenan left WWE for WCW in 1993. Vince McMahon's promotion was not quite the same without him.

    The things he did to make the pro wrestling business a better, more entertaining and interesting than it had been before he arrived. His ability to be the butt of the joke but, at the same time, make a wrestler more important by association made him a valuable asset for McMahon's promotion and the industry in general.

    Bobby Heenan was a once-in-a-lifetime talent.

8. Bret Hart

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    The wrestling landscape in 1997 was an ever-evolving one.

    There was no clear line between good and evil, black and white. There were only shades of grey. Fans no longer wanted to be told who to cheer and who to boo. They wanted to choose for themselves. They wanted their voices to be heard. For the first time, they were as much a part of the show as the performers themselves.

    Bret Hart was one of the first victims of the movement.

    An honorable and noble competitor, Hart was the hero to millions across the globe. An old-school wrestler from a wrestling family, he represented World Wrestling Entertainment with class and carried its heavyweight title with dignity.

    After losing an epic Iron Man match to Shawn Michaels at WrestleMania XII, Hart took time off. When he returned, he found a WWE he did not recognize.

    The hottest star in the industry was the foul-mouthed Steve Austin. He had attitude in abundance and had little problem opening up a can of, as he put it, whoop ass when necessary.

    Hart hated Austin and detested the fact that fans had gotten behind the rebellious redneck.

    At WrestleMania 13, Hart defeated Austin in a Submission match when the Texas Rattlesnake passed out from the pain of the Sharpshooter rather than tapping out. The fans in Chicago cheered the resilient Austin and booed the conclusion of the match, especially the declaration by ring announcer Howard Finkel that Hart had won the match.

    Enraged that Austin never officially submitted, Hart stomped away at his rival. The jeers that already flooded the Rosemont Horizon grew in number and volume. After being tossed to the mat by special referee Ken Shamrock, Hart left the ring looking anything like the heroic figure he was a year earlier.

    The following night on Raw, Hart expressed his frustration with American and its wrestling fans. He voiced his displeasure with their acceptance of Austin and of the way he had been screwed since returning some six months earlier.

    Over the weeks that followed, he reformed the Hart Foundation. The faction was made up of him, his brother Owen, brothers-in-law Davey Boy Smith and Jim Neidhart and Hart family friend Brian Pillman.

    Together, they waged war on World Wrestling Entertainment and its top stars, including Austin and Shawn Michaels.

    The unique thing about Hart's anti-American stance was that he was still the beloved star across the globe. Fans in India, Germany and the United Kingdom still chanted his name passionately. He remained a godlike figure in his home country of Canada.

    The only place he was treated as a villain, spit on and disrespected by the audience was the United States.

    It made for a unique atmosphere depending on where the night's show emanated from.

    He spent months leading assaults on Austin, Michaels and The Undertaker, but when July's In Your House: Canadian Stampede hit the airwaves from Hart's hometown, he received an ovation from fans that still ranks among the loudest of all-time.

    From March until November of '97, no one Superstar ignited as much passion in fans as Bret Hart.

    As has been well documented, Hart's career in WWE came to a controversial conclusion at the Survivor Series, in a screwjob that is still talked about to this day.

    He, like so many others on this list, was immortalized in the WWE Hall of Fame. His induction in 2006 came after years of hostility between him and Vince McMahon.

7. Ric Flair

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    While the majority of Ric Flair's legacy was built during his days in Jim Crockett Promotions, the NWA and World Championship Wrestling, he also proved to be one of the great heels in World Wrestling Entertainment.

    In late 1991, he defected from WCW and joined WWE, bringing with him the NWA World Heavyweight Championship. He referred to himself as the real World's champion, drawing the ire of the WWE fans, who had accepted Hulk Hogan as their champion for the better part of a decade.

    A lawsuit filed by WCW led to the disappearance of the World Heavyweight Championship from WWE television, but that would have little effect on Flair.

    When the WWE Championship was vacated following a controversial conclusion to a Hulk Hogan-Undertaker match at December 1991's This Tuesday in Texas pay-per-view, the title was put up for grabs in January's Royal Rumble match.

    Flair entered the match third and would outlast 29 other Superstars to win his first heavyweight title with Vince McMahon's promotion.

    His rivalry with Randy Savage leading into WrestleMania VIII would establish him as the top bad guy in the industry. He would repeatedly suggest that he and Elizabeth, Savage's wife, were having an affair and threatened to prove it to the world by hanging large banners of Elizabeth from the rafters of the Canseco Fieldhouse prior to their title match.

    Flair got what was coming to him at the event as Savage captured the title. But, as he always managed to do throughout his legendary career, he bounced back quickly and regained his title with the assistance of Razor Ramon.

    Flair's first stint with WWE would come to an end in 1993, but eight years later, after the fall of WCW, he would return to the company.

    As a heel, he would accompany Triple H to the ring and, more times than not, involve himself in The Game's matches. He assured that The Cerebral Assassin retained his title on many occasions before helping him assemble Evolution.

    The respect fans had, and still have, for Flair is a testament to the quality of his work across five decades.

    In 2012 he became the first, and only, two-time inductee in the WWE Hall of Fame.

6. Andre the Giant

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    The Eighth Wonder of the World was, and still is, one of the most beloved wrestlers in the history of the sport.

    Fans have fond memories of watching the larger-than-life Superstar dominate battle royals, bodyslam fellow giants and wave to the fans after yet another victory.

    In 1987, however, Andre destroyed his good-guy image forever when he shockingly formed an alliance with manager Bobby Heenan and set his sights on the WWE Championship, which was held by longtime friend Hulk Hogan.

    On that edition of Piper's Pit, Andre would rip the shirt and crucifix from Hogan's chest, as well as any remnants of their friendship.

    At WrestleMania III, Andre would enter the Pontiac Silverdome to a chorus of boos, the No. 1 contender to Hogan's title and top unquestioned top villain in Vince McMahon's promotion. Over 90,000 fans watched as he dominated Hogan for the majority of the biggest main event in the history of professional wrestling, only for the Hulkster to retain his title following a huge bodyslam and his signature leg drop.

    Andre would have a second opportunity to take the title from Hogan, and on February 5, 1988, he did just that. In the highest-rated wrestling match in network television history, Andre would end Hogan's four-year reign as champion amid enormous controversy.

    He would sell the title to Ted DiBiase in a moment that spawned the WWE Championship tournament at WrestleMania IV. 

    Andre would spend the next three years as one of the top heels in the industry, providing opposition to the likes of Hogan, The Ultimate Warrior, Jake Roberts and tag team champions Demolition.

    An iconic figure that transcends the business, Andre the Giant passed away on January 27, 1993.

    Later that year, he became the very first inductee into the WWE Hall of Fame, an institution that was created solely to honor him for all of his accomplishments in the business and everything he did for the company.

5. "Rowdy" Roddy Piper

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    "Just when you think you've got all the answers, I change the questions!"

    "Rowdy" Roddy Piper is not only one of the most beloved and popular heels of all-time, but also one of the very best pro wrestling villains ever.

    While both Vince McMahon and Hulk Hogan get ample amounts of credit for the success of World Wrestling Entertainment during the first boom period of the 1980s, Piper has been neglected by most.

    The fact of the matter is that every great good guy needs an equally great bad guy to accentuate his moral superiority. Batman needed The Joker, Superman needed Lex Luthor, and Luke Skywalker needed Darth Vader.

    Piper was the loud-mouth cheater who spoke his mind, even if what he had to say was not politically correct. He disrespected and verbally assaulted the numerous celebrities that played a major role in the success of the first WrestleMania and had fans anxiously anticipating the moment Hulk Hogan shut him up.

    Inside the hallowed halls of Madison Square Garden, Piper smashed a gold record over the head of Captain Lou Albano and proceeded to kick Cyndi Lauper. Fans erupted into a chorus of boos as security rushed the ring to try to subdue him.

    Throughout the builds to both WrestleMania and its sequel in 1986, Piper made comments could be construed as a bit racist when referring to Mr. T, an opponent of his at both events.

    It seemed as if no amount or intensity of heat was too much for Piper, who relished in the opportunity to be as bad as he wanted.

    Of course, with him as the top heel in the McMahon's promotion, the company thrived, and both WrestleMania events with him involved in high-profile matches proved to be tremendous successes.

    Even prior to his involvement with Hogan, Mr. T and the Rock and Wrestling angle, Piper was proving himself as a hated villain.

    One of the most iconic moments in sports-entertainment history came during an edition of Piper's Pit featuring Jimmy Snuka.

    Piper busted a coconut over Superfly's head and proceeded to beat him down. It was a great heel moment and one that current WWE Superstar CM Punk stated, on the WWE Home Video release CM Punk: Best in the World, made him a fan of pro wrestling.

    Whether he was insulting his foes or nearly inciting riots, Piper never failed to ruffle feathers throughout his career en route to his 2005 Hall of Fame induction.

4. CM Punk

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    The self-proclaimed Best in the World may have debuted with WWE's ECW brand in 2006, but it would not be until three years later when he began making his mark as one of the truly great heels of his generation.

    In 2009, Punk was drafted to the SmackDown brand. The Money in the Bank winner for the second consecutive year, he waited patiently for the most opportune time to strike and did just that following a ladder match between Jeff Hardy and Edge at Extreme Rules in June of that year.

    The fact that Punk cashed in his contract on Hardy, one of wrestling's most popular stars at that time, instantly earned him heat with the fans. It was one thing to cash on someone like Edge, who has among the top heels at the time, but it was another to do it on Hardy, especially after he had just survived a brutal ladder match.

    Over the weeks that followed, Punk insisted that he only did what everyone else would have and that there were no hard feelings between him and Hardy. But that was not the case. With every week that passed it, became clearer and clearer that Punk was not quite the admirable competitor he claimed to be.

    He intentionally got himself disqualified at June's The Bash in order to retain his title. It was after that moment when he began to show his true colors. He attacked Hardy's character and his past addictions to drugs. With every week that passed, he became more outspoken and his actions became more devious.

    The rivalry culminated in a steel cage match for the World Heavyweight Championship in which the loser of the bout would have to leave WWE. Punk defeated Hardy.

    Punk's next major angle would be the formation of the Straight Edge Society. It was a cult-like faction that followed Punk's Straight Edge code and pledged their allegiance to their leader. Serena Deeb went as far as to have her head shaved in the middle of the ring.

    The faction included the aforementioned Serena as well as Luke Gallows and Joseph Mercury. Under Punk, they because the hottest act on WWE programming but saw their run end unceremoniously when Serena was fired and they lost a series of matches against Big Show.

    Punk would continue his leadership role, this time as the head of the New Nexus. A lack of experience for the young performers of the group and a lack of passion and desire on Punk's end doomed the group from the start.

    The now-infamous "pipe bomb" promo, where Punk aired his grievances with WWE in front of the entire world, technically took place while he was still a heel but ultimately resulted in him becoming the hottest star in the business.

    After a year-long run as the second most over babyface in WWE, Punk returned to the dark side after leaving The Rock lying following a Go To Sleep on the Raw 1000 show in 2012.

    Punk said that, despite his lengthy run as WWE champion, he was being disrespected by the company. He denounced their focus on Rock and John Cena and said he should be the one to receive the attention.

    With Paul Heyman by his side, he remained one of the two top stars in the industry and, despite his bad boy tendencies, was as popular with the WWE Universe as any other member of the roster.

    His latest heel turn came to an end when he failed to defeat The Undertaker at WrestleMania 29.

    Punk remains as over as he does, regardless of his status as a face or a heel, because people appreciate the fact that he will speak his mind, he will not hesitate to call himself the best and he will take to the ring to prove it night-in and night-out.

3. The McMahons

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    Is it cheating to lump Vince, Shane and Stephanie McMahon in one large group? Yes.

    Is it my article? Darn skippy.

    The patriarch of the family, Mr. McMahon's heel turn came shortly after the 1997 Survivor Series. During a sit-down interview with Jim Ross, he took full responsibility for screwing Bret Hart out of the WWE title at that event and claimed he would do it again if necessary.

    From there, he made his dissatisfaction with the idea of Steve Austin becoming the poster boy for his company known to the world. He could not allow a beer-swigging, finger-flipping rebel to embarrass him or set a poor example for his company.

    McMahon made it his mission to toy with Austin and prevent him from representing WWE as its champion. He formed the Corporation, a stable of legitimate tough guys (and Pete Gas) whose job it was to protect McMahon and do his bidding in the war with Stone Cold.

    After this legendary, history-making angle with Austin reached its end, Vince would go on to feud with a number of WWE's top faces, including The Rock, The Undertaker, Ric Flair, Hulk Hogan and Bret Hart.

    Throughout his 15 years as an on-screen character, he has made the lives of many Superstars a living hell.

    His son Shane picked up right where Daddy left off, but he did so in a manner that differed from his father. He was less confrontational and far less aggressive. Shane had no problem sitting back and watching bigger, badder guys than himself tear apart his rivals.

    When the time came, however, Shane would willingly take to the ring to send a message.

    He has been a part of classic bouts, including the "Love Her or Leave Her" Greenwich Street Fight against Test at SummerSlam 1999, the brutal Street Fight against Kurt Angle at the 2001 King of the Ring and the Last Man Standing match against Kane at Unforgiven 2003.

    In 2001, Shane and his sister Stephanie led the WCW/ECW Alliance in an invasion of father Vince's WWE.

    Speaking of Stephanie, the Billion Dollar Princess is well on her way to becoming the most vile, ruthless member of the McMahon clan.

    In late '99, she turned her back on her father and revealed that she had not only been working with Triple H for weeks but that she had willingly married him just to spite Vince.

    For months, she and Triple H reigned over WWE, tormenting the top faces in the company.

    In March of 2000, she captured the Women's Championship and, despite having no real in-ring ability, held onto the title for five months. Over that period of time, she would defend the championship on a number of occasions, mostly against Lita. And every time she did, she would win thanks to outside interference from Tori or Trish Stratus.

    She would finally lose the title to Lita on the final Raw before SummerSlam 2000.

    More recently, Stephanie's role in the abuse of power angle involving her husband, COO Triple H, has seen her at her most deliciously evil. She has disingenuously referred to Big Show as her friend, only to humiliate and degrade him repeatedly.

    On the October 7 edition of Raw, she scorned him for his actions at Battleground before slapping him repeatedly and firing him on the spot. The way she spoke to Raw General Manager Brad Maddox was eerily reminiscent of the way her father would have talked to someone like former WWE commissioner William Regal back in the early 2000s.

    The McMahon family, more times than not, have made for entertaining and interesting television, leaving no doubt as to why they are among the most popular heels in WWE history.

2. "Macho Man" Randy Savage

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    Exploding through the curtain with a bright, sequins robe and the lovely Elizabeth by his side, Randy Savage was one of the most hated Superstars in World Wrestling Entertainment from his debut in 1985 until his babyface turn two years later.

    Savage was a consummate rule breaker in his WWE career.

    Throughout his early career, Savage would also prove to be less-than-chivalrous to Elizabeth. He would make her hold the ropes for him to enter the squared circle but never returned the favor. He never let her have any of what he believed should be his spotlight.

    He was even verbally abusive at times. That would change later, but it added to the heel persona that Savage was attempting to portray.

    On February 24, 1986, Savage defeated Tito Santana to win the Intercontinental Championship after using a foreign object to knock him out. Macho Man would hold onto the title in rematches against Santana and in a notable feud with George Steele that culminated in a WrestleMania 2 match.

    The extent to which Savage was willing to go to preserve his title reign, however, was never more apparent than on the November 22, 1986 episode of WWE's Superstars program

    After defeating Ricky "the Dragon" Steamboat by countout, Savage would assault him outside the squared circle before grabbing the ring bell and climbing the ropes. With Steamboat draped over the guardrail, Savage would come of the top with the weapon and crush Steamboat's larynx.

    It was a moment that left fans, especially the younger ones in the audience and watching at home, stunned and concerned for Steamboat's well-being.

    His recovery was part of a major angle that would reach its height at WrestleMania III, when Steamboat defeated Savage for the title in one of the greatest matches in wrestling history.

    Savage would spend the second half of 1987 and all of the following year as one of the two most popular stars in the promotion, winning the WWE Championship and forming a highly successful team with Hulk Hogan known as the Mega Powers.

    Unfortunately, jealousy crept in on Savage's part, and he soon reverted back to the ways that made him one of the top bad guys in the sport. He split with Hogan and kicked Elizabeth to the curb, forming an alliance with the hated Sensational Sherri.

    Savage would defeat Jim Duggan to become the King of WWE and would soon alter his name to reflect the honor. Now "Macho King" Randy Savage, he feuded with Dusty Rhodes throughout 1990 before turning his attention back to the WWE Championship.

    He wanted desperately to be granted a shot at the title, held by The Ultimate Warrior, but Warrior was not willing to simply hand him the opportunity. Despite attempts to beg and plead for a title by Sherri on Savage's behalf, Warrior still refused.

    At the 1991 Royal Rumble, Savage would make his presence felt a number of times during the title match between Warrior and Iraqi sympathizer Sgt. Slaughter. Savage would attack Warrior in the back of the arena before sneaking to ringside and blasting Warrior with a scepter across the head.

    Slaughter would win the title, and Savage and Warrior would be on a collision course to a high stakes match at WrestleMania VII.

    In a Retirement Match, Savage pulled every trick in the book in his attempt to defeat Warrior and end his career. He delivered five top-rope elbow drops and still could not keep the determined Warrior down. After falling victim to a series of high impact shoulder blocks, Savage would have his shoulders pinned to the mat and his career seemingly come to an end.

    After the match, Sherri berated Savage and physically abused him until Elizabeth rushed to the ring and dumped her to the arena floor. Elizabeth then showed concern for Savage and the two reunited in one of the most emotional and celebrated moments in WrestleMania's long and illustrious history.

    That reunion turned Savage from hated heel to beloved babyface, a role he would thrive in for the rest of his WWE career.

    Randy Savage passed away in May of 2011, leaving behind a legacy as one of the most popular, beloved and respected performers in wrestling history.

    He was the perfect combination of showmanship and workrate. He could talk, and he could back up his words with exceptional wrestling ability.

    He transcended wrestling and became a household name and internationally recognized pop culture icon, thanks in large part to his role as spokesman for Slim Jim.

1. "Stone Cold" Steve Austin

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    Photo Credit: WWE.com
    Photo Credit: WWE.com

    The Texas Rattlesnake led World Wrestling Entertainment to heights of popularity it had never seen before and championed a period in its history affectionately known as the Attitude Era.

    He sold boatloads of merchandise, packed arenas across the country and became a mainstream star thanks to his constant bucking of authority.

    You could not go anywhere without seeing at least one Austin 3:16 t-shirt on store shelves or on wrestling fans themselves.

    The stardom Austin achieved and the success World Wrestling Entertainment enjoyed because of it was the direct result of a heel run that established Stone Cold as one of the most must-see wrestlers in the business.

    As the Ring Master, Austin found it difficult to connect with the audience. His in-ring work was extraordinary, but with Ted DiBiase as his manager, he was rarely allowed to speak for himself.

    Once DiBiase left the company, Austin dropped the terrible gimmick and became "Stone Cold" Steve Austin, a cold and calculating Superstar who methodically picked apart opponents en route to victory. He also debuted a new finisher. After months of using DiBiase's Million Dollar Dream, he dropped the submission hold in favor of a Ace Crusher variation he dubbed the Stone Cold Stunner.

    Most important to the future success he would achieve was his change in attitude. He began to use profanity, which was not seen on Vince McMahon's more family-friendly shows. He had a swagger and an attitude to him that was completely different from what other WWE Superstars had at the time.

    Fans were sitting up and taking notice of the talented Texan already, but it was his King of the Ring 1996 performance that won him the hearts of wrestling fans.

    In his first match on the pay-per-view event, he suffered a severe laceration that required stitches. After pinning Marc Mero, he took a ride to the hospital for some medical attention. He made it back to the arena in time for the King of the Ring finals against Jake Roberts, though, and ultimately defeated him to win the tournament.

    After his victory, Austin would cut a promo that would summarize exactly who Austin wanted to be. Playing off of Roberts' born-again Christianity, Austin spouted off a few lines that would live forever in wrestling lore:

    You sit there and you thump your Bible, and you say your prayers, and it didn't get you anywhere! Talk about your psalms, talk about John 3:16... Austin 3:16 says I just whipped your ass

    That promo instantly made Austin a star. Fans across the country brought Austin 3:16 signs to arenas and cheered the surly Texan's every move, no matter how vile or despicable it was.

    Late in 1996, Austin would set his sights on Bret Hart. He would antagonize The Hitman, tear him down in promos and taunt him into returning to the ring for a match. He would make derogatory comments about the respected in-ring veteran, and to the surprise of many, a significant portion of fans would continue to support him.

    By the time the match between Austin and Hart happened at Survivor Series in 1996, Stone Cold had accumulated a great amount of momentum, and for the first time in years, it was clear that WWE had tapped into something special with a brand new talent.

    Austin and Hart's rivalry would continue into WrestleMania 13 in 1997. In a rare wrestling double turn, Austin became a babyface while Hart switched to the dark side for the first time in nearly a decade.

    There was no longer any use in portraying Austin as a villain when so many fans had accepted him as their blue collar hero.

    That decision to give into the want of the fans resulted in a renaissance for WWE. After two years of getting thumped in the Monday Night Wars by Ted Turner's WCW, Vince McMahon's promotion rode Austin and a new attitude to ratings dominance, eventually putting WCW out of business in 2001.

    Steve Austin was inducted into the WWE Hall of Fame in 2009.

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