Michael “P.S.” Hayes tells the story like this — in the thick of The Fabulous Freebirds’ heated rivalry with The Junkyard Dog in Mid-South Wrestling, the fans in Louisiana became so wrapped up in the dispute that the police once apprehended a man in the audience with a Saturday night special in his hand. In the chamber of the gun was a bullet with the word “Freebirds” engraved on it.

Things have changed since the all-or-nothing days of Southern wrestling, but the intent of a good ring villain remains. If the people buying tickets don’t want to see the bad guy get what’s coming to him, then the bad guy isn’t doing their job. It’s a dangerous occupation for the competitors and managers who have been insulted, stabbed and, on more than one occasion, shot at by the fans. But the wicked Superstars and Divas on this list wouldn’t have had it any other way. ( PHOTOS)

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50

Batista

Lex Luthor hated Superman because The Man of Steel became the savior of humanity and Metropolis, something Luthor strived for his entire life. That legendary comic book rivalry draws strong parallels to a WWE enmity between Batista and John Cena.

Although he broke out in WWE as the powerhouse of Evolution, Batista always despised being overshadowed. All of his villainous actions over the years came to light when he attacked John Cena to win the WWE Championship after Cena survived a grueling Elimination Chamber Match. Just as Superman became the savior of Metropolis, the Cenation leader had become the face of WWE — something that did not sit well with The Animal.

Finally, after years of questionable actions, Batista revealed his ultimate jealousy, believing he should be the face of WWE instead of Cena. Unfortunately for The Animal, he was unable to defeat Cena again and eventually tucked his tail and ran, quitting WWE altogether. — KEVIN POWERS

49

Randy Savage

Sure, “Macho Man” may now bring nostalgic smiles to the faces of the WWE Universe, but in his heyday, Randy Savage was the prime antagonist to WWE’s top heroes.

After debuting in WWE in 1985, Savage introduced the lovely Miss Elizabeth, but “Macho” often shielded his beautiful manager from the bright lights of stardom, much to the dismay of WWE fans. The unpredictable Superstar even accused Hulk Hogan of having “jealous eyes” for Elizabeth, and the two met in an iconic clash at WrestleMania V. Savage later donned the crown of “Macho King” and called on the devious Sherri to be his Queen. He targeted Ultimate Warrior with a series of heinous attacks, and the two battled in a Retirement Match at WrestleMania VII. “Macho” remained a villain during his days as a member of The nWo in WCW, and had a bitter rivalry against Diamond Dallas Page.

While Savage’s legacy left an indelible mark on the squared circle, was the “Macho Man” a macho villain? Oooh yeah. — ZACH LINDER

48

Vickie Guerrero

“Excuse me!”

By screeching this simple and seemingly innocuous phrase whenever she steps through the curtain, the shrill and shrewd Vickie Guerrero elicits an immediate response from crowds in arenas around the world. However, Vickie’s transgressions against the WWE Universe extend far beyond her numerous, ear-splitting aural affronts.

A former Raw and SmackDown General Manager, the self-professed “Queen Diva” has used her cunning business savvy and unique feminine wiles to repeatedly climb the corporate ladder and pull the necessary strings for her friends and business associates, including the likes of Team Lay-Cool, 2012 WWE Hall of Famer Edge and her current client, “Mr. Money in the Bank” Dolph Ziggler.

In WWE’s animal kingdom, this notorious “cougar” is always on the prowl and, as is the case in the wild, morality is seldom a factor when it comes to getting what she wants. — JAMES WORTMAN

47

Mark Henry

Some WWE fans were critical of the fact that it took Mark Henry 15 years to embrace his status as the squared circle’s most intimidating figure. Truth is they should be thankful. Had the powerhouse from Silsbee, Texas, spent the last decade behaving the way he did in fall 2011 then WWE history would look a lot different. Imagine rings destroyed. Legends hobbled. The Streak? A few digits less impressive.

So be grateful that Henry chose 2011 to construct what he called his “Hall of Pain” out of the broken bones of fallen opponents like Kane, Big Show and Randy Orton. Had nagging injuries not slowed him, Henry may have depleted an entire roster. Even fans in the front row seemed uneasy in the looming presence of the former Olympic power lifter.

Broadcasters who bandied around the word “monster” in regards to Mark Henry missed the point. Monsters are fiction. It is men that are real. And Henry was the meanest man of them all. — RYAN MURPHY

46

The Iron Sheik

The Iron Sheik was easily the most recognizable villain of his era.

Proudly claiming to have come from “10,000 miles away in Teheran, Iran,” the former bodyguard of Shah Mohammad Reza Pahlavi enraged American fans by flaunting his Arabic heritage. But The Iron Sheik wasn’t just a blowhard. A dangerous Greco-Roman wrestler, he garnered headlines on Dec. 26, 1983, when he humbled WWE Champion Bob Backlund in Madison Square Garden with the dreaded Camel Clutch.

In the years that followed, Sheik continued to draw the ire of fans in the U.S. as he aligned himself with Russian baddie Nikolai Volkoff and, later, Sgt. Slaughter when Sarge outed himself as an Iraqi sympathizer. — HOWARD FINKEL

45

Andre the Giant

What happens when the friendly colossus who could always be counted on to do what’s right turns his back on his friends? The WWE Universe found out in 1987, when Andre the Giant bitterly betrayed longtime ally Hulk Hogan. It began when WWE, in recognition of the giant’s 15-year undefeated streak, presented Andre with a trophy. One problem: "The Eighth Wonder of the World’s" trophy paled in comparison to a trophy Hogan received to honor his three-year WWE Title reign.

Andre stormed out of his ceremony, and the next time he appeared on TV, he had Bobby Heenan by his side. As Heenan claimed the giant was overdue for a title shot, Andre ripped off the cross from around Hogan’s neck, ending a friendship that years earlier saw Andre pour a celebratory bottle of champagne over Hogan’s head. Suddenly, the globe’s most beloved performer became WWE’s most hated Superstar. — JOHN CLAPP

44

Eric Bischoff

Eric Bischoff has been called many things throughout his sports-entertainment career. “Visionary” and “ambitious” have been used to portray the former WCW President, but the word “sleazy” has also been drawn to casually describe the man who nearly won the Monday Night War.

Bischoff’s reputation as “Sleazy-E” didn’t begin when he revealed himself to be a member of The New World Order. In fact, his earliest villainous acts weren’t even inside the squared circle — they came from behind a suit, a tie and a corporate desk. In 1994, Ricky “The Dragon” Steamboat was sidelined due to injury when he received a package from Bischoff containing his pink slip. In 1995, Steve Austin was out with an arm injury when he answered a phone call from the WCW President and was subsequently fired.

Inside the squared circle, following his revelation as the corporate power behind The New World Order, Bischoff had the power to bend the rules to serve Hollywood Hogan and the black and white clad faction’s needs. He offered no apologies for the decisions he made. — K.P.

43

Eddie Guerrero

One of Eddie Guerrero’s best-known mantras — “I lie, I cheat, I steal!” — sums up the darker side of the WWE Hall of Famer. In his early days competing south of the border, “Latino Heat” appalled fans by mocking their Mexican pride and gesturing as though they should be swimming to the U.S. Later on in WCW, he claimed his wallet had been stolen and in trying to find the perpetrator, forced every WCW luchador to break a time-honored lucha tradition by removing their masks.

Yet, none of these bad deeds could compare to the inglorious offensive Guerrero launched toward Rey Mysterio in 2005. Believing The Ultimate Underdog to be an ungracious tag partner and friend, he not only ended their team by bailing on Mysterio, but also sought to rip apart Rey’s very family by threatening to take custody of their son, Dominick, whom Guerrero had actually sired. — J.C.

42

Brock Lesnar

Throughout his entire career, Brock Lesnar has lived for one person and one person only: Brock Lesnar.

Making his WWE debut in 2002, Lesnar dominated anyone in his path and the WWE Universe loved every second of it. However, by the time WrestleMania XX came in 2004, he abandoned WWE to pursue a career in the NFL. During Lesnar’s match against Goldberg on The Grandest Stage of Them All, the WWE Universe turned their backs on The Next Big Thing and he responded with equal negativity to the crowd.

Fast forward eight years to the night after WrestleMania XXVIII, John Cena was still reeling from his loss to The Rock the night before when Lesnar made his shocking return to WWE. The WWE Universe was initially elated. However, the truth about Lesnar once again became clear. He was less interested in entertaining the fans and more interested in showing the world he was the toughest man alive — for a price. — K.P.

41

Kane

Freezing his father alive? Check. Electrocuting a McMahon? Check. Launching a wheelchair-bound Broski off the entrance ramp? Check. Burning and burying his half-brother alive? Checkmate.

In his fiery tenure with WWE, Kane did his part to heinously torment everyone who stepped in his path. Anytime he remotely hinted at remorse, The Big Red Monster became more despicable than ever.

Kane’s most vile behavior came after losing his mask in 2003. During an interview with Jim Ross, Kane flipped out on the helpless WWE Hall of Famer, saying he needed to “feel [his] pain.” The Devil’s Favorite Demon then attacked J.R. and doused him with gasoline. As the production crew pleaded for mercy and J.R.’s longtime friend, “Stone Cold” Steve Austin, watched helplessly from the arena, Kane ignited the legendary broadcaster.

Any Superstar willing to burn another defenseless human being warrants a spot as one of the baddest of all time. — JEFF LABOON

40

Don Muraco

Don Muraco backed up everything he said he was going to do inside the squared circle — and what he did was not revered by the fans.

Hailing from Sunset Beach, Hawaii, The Magnificent One rode the waves into WWE in 1981 and proceeded to dethrone the beloved Pedro Morales as Intercontinental Champion. From there, the powerful Muraco had many memorable matches in WWE rings, punishing a long list of WWE Hall of Famers, including "Superfly" Jimmy Snuka, Tony Atlas and Hulk Hogan.

It was Muraco who trapped The Hulkster in the corner and allowed King Kong Bundy to splash Hogan until his ribs buckled. Worse yet, The Magnificent One once ate a meatball sandwich in the ring while abusing a local schmo. It was pure arrogance, but who besides the man WWE fans mocked as a “beach bum” could have pulled it off? — H.F.

39

The Dudley Boyz

Bubba Ray and D-Von were the epitome of villains. They spewed vitriolic, profanity-filled diatribes with the sole purpose of breeding hostility. As Bubba once said, “We were the worst of the worst. We were the most in-your-face, disgusting, hated people to ever step foot in an ECW ring. And I think anybody that came through ECW would say the same thing.”

During a May 1999 match in Detroit, they lit a table on fire for the first time, and powerbombed Balls Mahoney right through it. Later that year, they nearly incited a genuine riot at Heat Wave by getting a little too close to ringside ticket-holders. But no one could deny the success of the multi-time champions.

Paul Heyman said it best, “The Dudleys are the greatest team in the history of ECW bar none. They egged on a crowd and antagonized the audience more than any other act in the history of this business, and they were fearless in doing it.” — Z.L.

38

CM Punk

Arriving in WWE in 2006, CM Punk quickly earned respect from the WWE Universe due to his work ethic and tremendous discipline. But in 2009, Punk cashed in his Money in the Bank contract to win the World Heavyweight Championship from Jeff Hardy, and immediately began insisting he was Hardy’s moral superior.

Punk’s actions began to take a turn for the sinister. He grew out his beard and formed The Straight Edge Society, a posse of cult-like converts who praised Punk’s preachy straight edge sermons as gospel. Punk’s followers even shaved their heads in the ultimate display of loyalty to their drug-free chieftain. No one was safe from Punk, who harassed Rey Mysterio’s young children, and momentarily took the 2010 Royal Rumble Match hostage. When The Nexus was in a state of transition, they turned to Punk for his résumé of villainous leadership and ability to influence the masses.

"Pipe bomb" or not, when CM Punk preaches, the world pays attention. — Z.L.

37

Ernie Ladd

One of the few individuals to successfully make the transition from pro football to wrestling, Ernie Ladd meant business in every sense of the word. Tall and tough, the 6-foot-9 “Big Cat” carved his niche during the ’70s and ’80s, when he became one of the most hated villains of his day. When he spoke, people listened, and that translated into capacity crowds at arenas, hoping to see him get his comeuppance.

One of Ladd’s meal tickets to success was his “taped thumb.” Ladd claimed that he received that through an old football injury, but when the going got tough, he put it to good use to gain his victories. Ladd left his mark during the territorial days against such stars as Wahoo McDaniel (Mid-Atlantic/Florida), Mr. Wrestling (Georgia), and The Junkyard Dog (Mid-South). His WWE tenure in the ’70s included taking WWE Champions Bruno Sammartino, Pedro Morales and Bob Backlund to the limit. — H.F.

36

Ivan Koloff

He was the man who shocked the wrestling world. Ivan Koloff became a household name in Madison Square Garden on Jan. 18, 1971, when he ended Bruno Sammartino’s nearly eight-year reign as WWE Champion. The eerie hush that fell over the New York City crowd as they watched their Italian hero fall was downright haunting.

Although he only held onto the title for 21 days, The “Russian Bear” gained more confidence after that fateful evening and became one of the most despised foreign villains to ever set foot in the ring. As the Cold War between the United States and Russia heated up in the ’70s and ’80s, the proud Soviet terrorized the likes of Dusty Rhodes and The Rock ‘n’ Roll Express in the NWA alongside his nephew, Nikita, Krusher Kruschev and other aggressive Russians. — H.F.

35

Paul Heyman

There was nothing the man once known as Paul E. Dangerously wouldn’t do to make audiences hate every fiber of his being. Case in point, he once had to be rushed from the ring by police after mocking the plight of Georgia peanut farmers who were in dire financial straits because of a drought.

As an announcer in WCW, Heyman incensed TV viewers by undermining WWE Hall of Famer Jim Ross. As a manager, Heyman directed Superstars like “Ravishing” Rick Rude and Brock Lesnar to destroy beloved legends like Ricky “The Dragon” Steamboat and Hulk Hogan. But it was the men in power who the brusque New Yorker incensed the most.

No matter how many times employers tried to banish him, Heyman always returned to be an even more painful thorn in their side. His most recent reemergence in WWE is proof that only cockroaches are more inexorable than the mad scientist of sports-entertainment. — JOEY STYLES

34

Abdullah the Butcher

Uncivilized monsters aren’t uncommon in sports-entertainment. Kamala the Ugandan Giant, Umaga and The Missing Link all made their mark. But no competitor was ever as savage as Abdullah the Butcher.

Internationally feared for his lust for flesh, The Madman from the Sudan routinely caused riots in Puerto Rico when he bludgeoned their national hero, Carlos Colon, and horrified the fans in Japan by taking a dinner fork to the forehead of the iconic Terry Funk. A renowned villain since the early 1960s, Abby terrorized the biggest stars in the world for more than five decades. He carved up Bruiser Brody in Texas, stalked Sting in Atlanta and waged a gory war with The Sheik in Detroit. Even at the geriatric age of 71, Abdullah is still raising hell.

A 2011 WWE Hall of Fame induction was meant to humanize The Butcher, but it didn’t stop him from hitting the podium wild-eyed with rusty fork in hand. — R.M.

33

Terry Funk

Terry Funk found great pride in infuriating fans and instigating them to the point of action. While in Florida, he declared fan favorite Dusty Rhodes to be a "yellow, egg-sucking dog.” In Memphis, Tenn., he accused hometown hero Jerry Lawler of being a "lover of chickens.” It may come as little surprise, then, that the crazed man from the Double-Cross Ranch in Amarillo, Texas, once described fan riots as a “form of flattery.”

But all that served to make Funk strangely endearing, not villainous. If you want to find an act that will forever live in infamy, look no further than The Funker’s heinous attack of NWA Champion Ric Flair in 1989. While Flair was in action, Funk jumped him from behind and wrapped a plastic bag around his head. Much more than an attempt to hide Naitch’s unmistakable bleached blond locks, Funk’s ambush was a (thankfully) unsuccessful attempt to suffocate the champion. — J.C.

32

Randy Orton

Like any true serpent, The Viper has chilled blood circulating through his body. In fact, Randy Orton’s is among the coldest of any athlete to ever perform in WWE.

Alluring a sight it may be, the RKO has been a weapon of ruin ever since Orton was first christened “Legend Killer” in 2003, when no venerable ring icon was exempt from his contempt. Orton’s shift of focus from legends to championships is when he proved most dangerous. If he wasn’t aligned with villains like Edge or Triple H, The Viper was slithering up behind them to strike and assume their accolades as his own.

Don’t blame the IED. The heap of fallen humanity in the distance is handiwork of the calculating third-gen Superstar, who RKO’d John Cena throat-first onto a steel chair, punted WWE’s Chairman and kissed Stephanie McMahon to get cerebral with The Game, all to be acknowledged (even feared) as what he is today: WWE’s Apex Predator. — CRAIG TELLO

31

Kevin Sullivan

It’s hard to imagine that the short, stocky guy with the thick Boston accent could be the living embodiment of Satan. However, that was very much the case with Kevin Sullivan.

A former good guy in other territories, Sullivan began to explore the darkest depths of evil after arriving in Championship Wrestling from Florida. Declaring himself to be “The Prince of Darkness,” he unleashed hell on heroes like Dusty Rhodes, Blackjack Mulligan and Barry Windham.

He didn’t come alone, either. He conjured up a cult-like army of evil. Sullivan used Satanic spells to draw the mysterious Purple Haze from the depths of the sea. His haunting army grew as stars like Jake Roberts and “Superstar” Billy Graham fell under the spell of “The Prince of Darkness.”

Sullivan brought the dark arts to WCW in the mid-1990s, leading the Dungeon of Doom into a war to stop Hulk Hogan. — BOBBY MELOK

30

Jerry Lawler

Make no mistake — Jerry “The King” Lawler was once as despised as he is now beloved. Honing his notorious acerbic wit in his hometown Memphis, Tenn., during the 1970s, Lawler declared himself the savior of wrestling. But he wasn’t all talk — The King employed foreign objects like a steel chain to win matches, often assisted by his managers Sam Bass and Jimmy Hart.

Lawler brought his brand of villainy to WWE in 1993 by brutally attacking King of the Ring winner Bret Hart. The two kings battled for more than two years in one of WWE’s most heated rivalries, with Lawler constantly scheming his way out of matches with the “Hit Man.”

No target was safe from “The King,” who even invaded Philadelphia’s ECW Arena in 1997. Settling at the broadcast booth, Lawler became one-half of the iconic Attitude Era commentary team, often sympathizing with WWE’s biggest baddies, much to the frustration of Jim Ross. — Z.L.

29

Raven

No ECW grappler was more despised than the sadistic Raven. Arriving in 1995, the man from The Bowery became the company’s prominent antagonist and always made things personal. His eloquent manner of speech was in direct contrast to Raven’s signature look of greasy, long hair, torn jeans, leather jacket and plaid shirt tied around his waist.

The influence of Raven and his Nest of henchmen was clear in his intense rivalry with The Sandman. He brainwashed The Sandman’s son into denouncing his father, and later crucified the beer-swilling brawler at ringside. Kurt Angle was so offended by Raven’s actions, he refused to join ECW.

After Tommy Dreamer earned the respect of the Philadelphia faithful, Raven revealed that they had been summer camp adversaries when Tommy was a popular jock. As the rivalry escalated, the two battled many times for more than two years. Dreamer was never able to topple his grungy rival until Raven’s final night on the roster when Tommy was finally able to quoth, “Nevermore.” — Z.L.

28

The Fabulous Moolah

Truly one of the all-time greats from a feminine side of things was the ageless Fabulous Moolah. Born Lillian Ellison in Columbia, S.C., Moolah exuded a “Southern Belle” charm to everyone she encountered — except when she competed in the ring, where her persona was the exact opposite.

For the better part of seven decades, Moolah’s modus operandi was to win at any and all costs. She knew how to break the rules in the most innocent of ways and it earned her the reputation of being one of the ring’s most difficult female competitors to defeat. Many tried, but very few succeeded in accomplishing that feat.

Moolah won the Women’s World Title in 1956 and used every dirty trick in the book to retain it for the next 28 years. The WWE Hall of Famer was also an integral part of the fabled Rock ‘n’ Wrestling Connection, where she terrorized the beloved Wendi Richter. — H.F.

27

Paul Orndorff

Following his loss to Hulk Hogan and Mr. T at the inaugural WrestleMania, “Mr. Wonderful” Paul Orndorff had a change of heart. He ditched Bobby “The Brain” Heenan and joined forces with The Hulkster.

Orndorff was mocked as “Hulk Jr.” by Heenan and “Adorable” Adrian Adonis for being Hogan’s lackey. But when “Mr. Wonderful” tried to get his friend to team up with him against Heenan’s pair of Big John Studd and King Kong Bundy, Hogan allegedly let the calls go to voicemail. When The Hulkster finally agreed to face the giants with his pal, the damage had been done.

With his partner in peril, Orndorff hung out on the apron, feigning interest in helping Hogan. When he finally came to his partner’s aid, “Mr. Wonderful” cleared the ring of the monstrous opposition before viciously piledriving Hogan to the canvas. Orndorff earned the ire of Hogan and the WWE Universe, becoming one of the most hated figures in WWE history almost instantly. — B.M.

26

Nick Bockwinkel

It would be easy to call Nick Bockwinkel the original “Cerebral Assassin.” After all, the former AWA Champion could expound on the intricacies of his Sleeper Hold like a college professor holding a master's class. But Bockwinkel didn’t play assassination games. Where other bad guys would resort to sloppy brutality against their seemingly unstoppable opponents, “Wicked Nick” kept his cool, taking a clinical approach to the dissection of a rival. It was that rationality that made him so dangerous.

A mosquito on the neck of Minnesota legend Verne Gagne, Bockwinkel dominated the AWA as champion for seven years with his unique ability to walk away with the title even when he lost. Hulk Hogan and The Crusher were just a few of the challengers to beat Bockwinkel, only to find that he had taken advantage of an overlooked line in the rulebook to reverse the decision.

The WWE Hall of Famer often said he was the smartest man in wrestling. He wasn’t lying. — R.M.

25

Vader

Few men have run roughshod over sports-entertainment like Vader. The Mastodon was pure fear packed into a 6-foot-5, 450-pound frame. Rampaging across the globe, Vader destroyed WWE Hall of Famer Antonio Inoki in Japan, brutalized El Canek in Mexico and severed Cactus Jack’s ear in Germany.

Even WCW’s Sting was no match for the monster. Vader steamrolled The Stinger on multiple occasions, including a vicious White Castle of Fear Strap Match. After leaving WCW’s top stars in shambles and capturing the Atlanta-based promotion’s World Title on three occasions, Vader moved on to WWE.

Shortly after his debut, The Mastodon made a lasting impression on the WWE Universe when he brutally assaulted President Gorilla Monsoon. Vader was a looming threat for any WWE Superstar, as few competitors wanted to willingly step in the ring with the monster. — B.M.

24

Harley Race

Though he was a technical mastermind, Harley Race was never afraid to get dirty in order to get the duke. Nor was he afraid to hire other grapplers to take out his opponents. Having tired of Ric Flair’s attempts to take his NWA World Championship, Race posted a $25,000 bounty for anyone who could take The Nature Boy out permanently. He cackled delightfully as he watched Dick Slater and "Cowboy" Bob Orton break Flair’s neck and collect the cash.

Flair recovered and got retribution, defeating Race for the title at the inaugural Starrcade. In the following years, however, Race’s arrogance soared to new heights. When he arrived in WWE in 1986, he won the King of the Ring tournament and wore his cape and crown everywhere. Upon his victories, Race forced his fallen opponents to bow before him and acknowledge his superiority. — B.M.

23

Sgt. Slaughter

His boots were always polished. His jutting jaw was recognizable from a mile away. And his aggressive nature against heroes like Tito Santana and Ricky Steamboat made him instantly hated. His name was Sgt. Slaughter and although he is recognized today as a patriot and a WWE Hall of Famer, things weren’t always that way for the Superstar from Parris Island, S.C.

When Sgt. Slaughter entered WWE in 1980, the former Marine made life miserable for WWE Champion Bob Backlund, repeatedly abusing the good guy in brutal matches. Sarge could be vicious, as he displayed in his landmark 1981 Alley Fight against Pat Patterson in Madison Square Garden, but he became abhorred in 1991 when he turned his back on the U.S. and outed himself as an Iraqi sympathizer. With the Persian Gulf War raging at the time, Sarge’s turn drew so much controversy that WrestleMania VII had to be relocated for Slaughter’s safety. — H.F.

22

The Undertaker

Loved, feared or respected? The Undertaker is all three. But he’s built a hell of a lot of equity as a malicious specter who haunts sports-entertainment and, for years, cast a tall, dark shadow over WWE.

The wicked thoughts in The Phenom’s mind are the substance of nightmares. The worst part? How many times he’s acted on those thoughts. Over the years, Undertaker has hurled human beings off the top of 20-foot cells and symbolically zipped them up in black vinyl bags. As a minister of the dark arts, The Deadman captured and tried to wed an innocent Stephanie McMahon, among other ritualistic acts like setting ablaze his cross-like emblem on the McMahons’ front lawn. We won’t even discuss the stuffed bear.

There’s been no grave to hold the body down of this originator of macabre villainy in the squared circle — probably because even hell won’t have a demon like The Undertaker. — C.T.

21

Freddie Blassie

Known as the “Hollywood Fashion Plate,” Fred Blassie epitomized every aspect of what a true wrestling villain should be: sly, cunning and smart. He knew how to break every rule in the book.

Blassie received worldwide recognition for his dastardly deeds. While facing Japanese legend Rikidozan in the early ’60s, he gnawed at his opponent’s forehead and left him with a crimson mask, terrifying an entire nation. He supposedly kept his teeth sharp by using a file on them, as Rikidozan found out. If fan ire was a stock, shares would always be up as it related to how Blassie played with their emotions.

As his in-ring career as a wrestler wound down, Blassie entered the arena of managing, and found a great measure of success along those lines. Imparting some of his years of chicanery on The Iron Sheik, Killer Khan and Nikolai Volkoff, the WWE Hall of Famer left a permanent mark on WWE that remains to this day. — H.F.

20

Edge

If seizing opportunities no matter the circumstances is a characteristic of a true villain, then no Superstar in history lives up to that principle more than Edge.

In 2005, Edge became the first Money in the Bank winner at WrestleMania 21, creating an opportunity that would define his career. At New Year's Revolution 2006, John Cena successfully defended the WWE Championship inside the unforgiving Elimination Chamber. Before the show ended, however, Edge cashed in his World Title contract and defeated an exhausted Cena to win the title.

In his quest to become legend, Edge stole Lita from his friend, Matt Hardy, and allied himself with villainous Superstars such as Randy Orton. He even engaged in a relationship with SmackDown General Manager Vickie Guerrero for no other reason than to advance his own career. The Rated-R Superstar's cunning, unapologetic and opportunistic nature defined him as one of the most hated and brilliant villains in WWE history. — K.P.

19

Jim Cornette

A spoiled, rich mama’s boy, Jim Cornette chose to use his family’s wealth to put together a stable of grapplers capable of capturing championships.

Clad in some of the most garish suits in sports-entertainment history, Cornette’s whiny voice grated on fans throughout the southern United States as he led a coterie of baddies including The Midnight Express and Big Bubba Rogers. There was no level Cornette was afraid to stoop to in order to get one up on the competition. When it looked like The Fantastics were on the verge of unseating The Midnight Express as U.S. Tag Team Champions, Cornette led Sweet Stan Lane and Beautiful Bobby Eaton in a brutal leather strap lashing of the challengers.

Cornette brought his brand of villainy to WWE in 1993, when he was hired as the spokesperson for Japanese WWE Champion Yokozuna. Mama Cornette’s pride and joy went on to annoy the do-gooders in WWE for years. — B.M.

18

Killer Kowalski

There was no denying the credentials of WWE Hall of Famer Walter “Killer” Kowalski. Strong on conditioning and smart on in-ring skills, Kowalski employed an aggressive, “no mercy” style toward his opponents that more times than not ended with his dreaded Stomach Claw.

One of Kowalski’s most notable aggressions took place in 1954 in a match against Yukon Eric. With his opponent down, Killer dropped a knee and took off a part of Eric’s ear, strengthening Kowalski’s reputation as a ruthless competitor in the ring.

In the decades after that incident, Kowalski’s reputation continued to spread as he attacked an Australian talk show host on live television and put boxing great Jack Dempsey in the hospital. And in later years, Killer imparted his wicked wisdom of the squared circle to eager learners, as he trained future villains like Big John Studd and Triple H. — H.F.

17

Mr. Perfect

Basketball, bowling, table tennis, darts, diving, you name it, Mr. Perfect was, well, perfect at it. And he never let WWE fans forget it. Oh yeah, he was flawless in the squared circle, too.

The Minnesota native’s cocky attitude rubbed nearly the entire WWE Universe the wrong way. He didn’t care, though, as it paid off in the ring. Finishing off opponent after opponent with his patented Perfect-Plex, the consummate technician went undefeated for more than a year.

In addition to capturing the Intercontinental Championship on two occasions, Mr. Perfect was a constant thorn in the side of WWE Champion Hulk Hogan. Perfect was so fixed on taking Hogan’s title that he stole it and destroyed it with a hammer, declaring that he was the “perfect champion” and that no one but him deserved to wear the title. — B.M.

16

Sherri Martel

There is an old saying that “behind every great man is a great woman.” During the 1980s and 1990s in WCW and WWE, behind every great villain was Sherri Martel.

Known as “Sensational” Sherri, the lovely lady was a pioneer for women in sports-entertainment and a true antithesis to another 1980s mainstay, Miss Elizabeth. A former AWA and WWE Women’s Champion, Sherri mastered her craft under the guidance of The Fabulous Moolah. As a manager, Sherri was most closely associated with “Macho King” Randy Savage, "The Million Dollar Man" Ted DiBiase, Ric Flair and Shawn Michaels.

Whenever a competitor matched up against someone who had Sherri in their corner, they had to keep their eye on the tough-as-nails Diva because she was never afraid to get herself physically involved. On more than one occasion, Sherri would break down gender lines and interject herself into the fray to give her competitor an edge. — K.P.

15

Chris Jericho

Chris Jericho’s early antics were often as comical as they were infuriating, but The Ayatollah of Rock ‘n’ Rolla soon established himself as a threat to wrestling’s greatest heavyweights. After breaking down the walls in WWE, Jericho shocked the world when he defeated “Stone Cold” Steve Austin and The Rock in the same night to become the first Undisputed Champion in history, a fact Jericho allows no one to forget.

As he began to amass one accolade after another, Jericho’s demeanor morphed from flamboyant loudmouth to calculating sociopath. No less pompous, he traded in the glittered vests for pinstriped suits, and chopped off his signature, long blond locks. Speaking in hushed tones with a mighty vocabulary, Jericho verbally eviscerated Shawn Michaels and got personal with CM Punk’s family and straight-edge lifestyle.

Chris Jericho is arrogant enough to refer to himself as "The Best in the World at What He Does," and the worst part is: He may be right. — Z.L.

14

The Original Sheik

Few competitors struck fear into the hearts of opponents and fans like The Sheik. From the moment he stepped on American soil in the 1960s, the Syrian madman introduced a brand of hardcore carnage that had been unseen in the squared circle.

Nothing was off limits for The Sheik. He would open wounds by biting the opposition. When the official looked away, he’d make things worse by attacking the victims with an extra-sharp pencil. And to top it all off, The Sheik would viciously toss a fireball into his foe’s face, blinding and burning them as crowds shrieked in horror.

The Sheik terrorized sports-entertainment for decades, making life hell for Bobo Brazil, Freddie Blassie, Bruno Sammartino and other heroes. When he decided to hang up his boots, he kept his sadistic tendencies in the family, teaching his nephew, Sabu, how to torture opponents. The death-defying maniac learned well, introducing hardcore wrestling to a new generation of fans in ECW. — B.M.

13

The Fabulous Freebirds

Michael “P.S.” Hayes, Terry “Bam Bam” Gordy and Buddy “Jack” Roberts embodied everything Southern wrestling fans loved. The fast-living, whiskey-drinking rock ‘n’ rollers should have been idolized in Texas’ World Class Championship Wrestling. But when Gordy cost Kerry Von Erich the NWA World Title by slamming a steel cage door on his head on Christmas night 1982, The Fabulous Freebirds became the most reviled team in sports-entertainment.

The dastardly trio had more than just The Von Erichs coming after them for retribution, because audiences were just as rowdy. Fans slashed their tires and smashed their windshields to the point where police had to drive them from the station to the arena — until fans slashed the cops’ wheels too. Michael Hayes isn’t exaggerating when he tells stories of crowds coming after them with knives or the more creative ones filling up squirt guns with Liquid-Plumr and attempting to blind them, just to help their idols get one up on the boys from Badstreet, USA. — B.M.

12

JBL

Known mostly as a rough cowboy for much of his career, Bradshaw was encouraged in 2004 by sniveling SmackDown General Manager Paul Heyman to embrace his Wall Street success. The following week, the former APA member reinvented himself as John Bradshaw Layfield.

Flaunting the millions he made off shrewd investments, JBL shockingly defeated Eddie Guerrero to win the WWE Championship at The Great American Bash. The J.R. Ewing clone became the longest reigning WWE Champion in 10 years, but titles weren’t enough for him. He rolled to the ring in a longhorn limousine, claimed to be a “Wrestling God” and humiliated WWE Hall of Famer Shawn Michaels by forcing HBK to do the millionaire’s bidding.

Loathed by fans and opponents alike, the arrogant investor had the last laugh as he retired to a tropical island with millions of dollars in his bank account. Whoever said "money can’t buy happiness" never saw the smile on this man’s face. — Z.L.

11

Rick Rude

"Ravishing" Rick Rude defined the meaning of arrogance more than any other Superstars in WWE history. Looking as if Michelangelo chiseled him from marble, Rude oozed machismo and backed it up with impressive agility inside the squared circle.

The former Intercontinental Champion was unapologetic in his taunts to both opponents and the WWE Universe. Overwhelmed with boos from the men in the audience as he made his way to the ring, Rude would draw more ire by referring to them as "sweathogs" or "sleazy city-dwellers" and then proceed to disrobe and flex for the enjoyment of the women filling the arenas.

Adding to his unrivaled arrogance, Rude's ring attire often featured an airbrushed image of either himself with a sanctimonious smirk, his opponent or a title he desired. Most notoriously, while trying to get inside the head of Jake "The Snake" Roberts, Rude tried to woo Roberts' wife Cheryl, going as far as airbrushing her face on the front of his ring gear. — K.P.

10

Jake "The Snake" Roberts

The moniker started, innocently enough, as a tribute to quarterback Ken “The Snake” Stabler, an Oakland Raiders general who slithered past defenders. But after years of stalking to the ring with a python in a burlap sack slung over his shoulder, it became more than just a nickname for Jake Roberts.

As cunning and heartless as a serpent, Roberts nearly ended Ricky “The Dragon” Steamboat’s career when he drove his head into the concrete floor with a DDT. Even worse, he once tied a helpless Randy Savage in the ring ropes and forced a poisonous cobra to sink its fangs into "Macho Man’s" forearm. Psychologically, "The Snake" was even more dangerous as he used mind games to cripple foes like Ultimate Warrior.

Roberts was always effective, but few could deny that he went too far. By the end of his career, it was hard to tell where Jake ended and "The Snake" began. — R.M.

9

Gorgeous George

George Wagner took sports-entertainment from black and white to Technicolor when he stepped into the squared circle wearing lavish robes and coifed platinum hair under the name of Gorgeous George.

Emerging from obscurity at the dawn of the television era, the WWE Hall of Famer turned the accepted sneer and snarl of wrestling villainy on its cauliflower ear in the early 1940s. Where other baddies spit and stomped, the self-proclaimed “Human Orchid” allowed a manservant named Jeffries to perfume the ring with Chanel before his bouts and recoiled in mock horror when referees attempted to check him for foreign objects. With that, George created the preening prima donna archetype of wrestling depravity that everyone from Ric Flair to Dolph Ziggler would later adapt.

This unmatched influence extended beyond the squared circle to include icons like Muhammad Ali and James Brown who credited "The Toast of the Coast" for inspiring their bad boy alter egos. — R.M.

8

Bobby Heenan

The greatest manager in wrestling history was also the most devious. Bobby Heenan was “The Brain” behind some of WWE’s toughest brawn of the 1980s, and used his keen intellect to scheme his clients’ into the main event — he was known as The Weasel for good reason.

After a star-making tenure in the AWA, "The Brain" brought his version of class to WWE in 1984. A key figure in many of WWE’s greatest rivalries, Heenan led villainous Legends like Andre the Giant, Mr. Perfect and Rick Rude to championships against WWE’s top heroes. In late 1991, Heenan played an instrumental role in wooing reigning WCW Champion Ric Flair to WWE, and in a memorable moment, "The Brain" compared Flair’s title to ice cream and Hogan’s WWE Championship to horse manure.

After retiring from managing, Heenan became the inciting half of an iconic commentary team with Gorilla Monsoon. His cutting wit infuriated his partner, often prompting Gorilla to beg, “Will you stop?!” Thankfully, The Weasel never did. — Z.L.

7

"Superstar" Billy Graham

“Superstar” Billy Graham reimagined what it meant to be a ring villain. His bleached blond hair, feather boas, tie-dye and chiseled physique were a tremendous influence on future greats like Jesse “The Body Ventura, Hulk Hogan and countless others.

In 1977, Graham ended Bruno Sammartino’s WWE Championship reign by using his feet on the ropes for leverage. During that era, villains did not maintain a stronghold on the title, and were often quickly defeated by the ring’s heroes. But Graham remained WWE Champion for an astonishing 10 months — a record among villains that stands to this day.

“Superstar” sold out 19 of the 20 events he headlined at Madison Square Garden. In 2004, he was inducted in the WWE Hall of Fame in the place that made him famous, New York City. Graham was certainly “the man of the hour, the man with the power, too sweet to be sour” and defined what it meant to be a “Superstar.” — Z.L.

6

Triple H

I nicknamed Triple H “The Cerebral Assassin” for good reason. The eight-time WWE Champion is the consummate thinking man’s wrestler who has studied the greats of the game since he was a teen. Taking a little from the best rule breakers in the profession such as Harley Race and Ric Flair, among others, and then incorporating what he saw into his repertoire, Triple H worked tirelessly to mold himself into the best villain of his generation.

Notwithstanding his unequaled wrestling IQ, Triple H also possesses legitimate physical and mental toughness — two traits that must exist in any legend. Tearing his quadriceps — the thigh muscle which is the largest muscle in one’s body — off the bone and still finishing the match proved that The Game was a rare athlete with bona fide grit. For my money, no one has ever been a better wrestling villain. — JIM ROSS

5

"Hollywood" Hogan

July 7, 1996, is a day that will forever live in sports-entertainment infamy. With the execution of one Atomic Leg Drop to his supposed ally “Macho Man” Randy Savage, Hulk Hogan went from a red-and-yellow clad personification of all that is good to one of the most notorious villains in sports-entertainment history. That evening — alongside Kevin Nash and Scott Hall — The New World Order and “Hollywood” Hogan were born. Clad only in black and white, Hogan rewrote the rules and played by his own, spray-painting the prestigious WCW World Title and anyone who dared challenge the faction with the three letters that defined the late 1990s, “nWo.”

Hollywood Hogan was arrogant, ruthless and did everything in his power to keep the WCW Title in his grasp. But like a true villain, Hogan would cower behind the ranks of The New World Order whenever he was threatened by WCW’s face-painted franchise, Sting. — K.P.

4

The Million Dollar Man

"The Million Dollar Man" Ted DiBiase was the one percent before there was a one percent.

Like Scrooge McDuck without the three nephews to balance him out, the wealthy Superstar cared for nothing but money and took pleasure in taunting those less fortunate. Most infamously, "The Million Dollar Man" Ted DiBiase offered a young fan $500 to dribble a basketball 15 times. On the 14th bounce, the WWE Hall of Famer kicked the ball away from the boy and sent him home with empty pockets.

Young WWE fans weren't the only ones the villain took pleasure in humiliating. Whenever he defeated an opponent inside the squared circle, "The Million Dollar Man" would stuff wads of filthy cash into the unfortunate competitor's mouth. Using his vast fortune for devious purposes extended beyond his tenure in WWE and into WCW. Shortly after The New World Order was formed, he was revealed as their financier. — K.P.

3

Mr. McMahon

What kind of egomaniacal monster would have his own daughter kidnapped and offered up as a sacrifice to The Ministry of Darkness? The same individual who masterminded the notorious “Montreal Screwjob”: the incomparable Mr. McMahon. The Chairman's shrewd business acumen mixed with his "survival of the fittest" approach to sports-entertainment has cemented his legacy as a larger-than-life scoundrel in the history of the industry he revolutionized.

Sure, it began at Survivor Series 1997 when he screwed Bret "Hit Man" Hart out of the WWE Championship, but that moment was simply the tip of the iceberg when it comes to Mr. McMahon's wicked deeds. The boss who publically butted heads with “Stone Cold” Steve Austin during WWE’s “Attitude Era” has been known to make life hell for anyone who dares defy him, even forcing a handful of competitors to join an exclusive club.

The Chairman rules WWE with an iron fist and anyone brazen enough to stand up to him may be the recipient of two famous words: “You’re fired!” — K.P.

2

Ric Flair & The Four Horsemen

There is no faction in the history of sports-entertainment that defined villainous more than The Four Horsemen.

No matter what Superstars filled out their ranks, The Horsemen’s goals remained the same: being the diamond standard in sport-entertainment. With the incomparable “Nature Boy” Ric Flair leading the charge, The Four Horsemen were unrepentant in their brazen attacks on their opponents or those that didn’t fit their limousine-riding, jet-flying lifestyle. In their most appalling act, the group chased down Dusty Rhodes in a parking lot and broke his hand.

The Four Horsemen refused to play nice and crossing one of them would mean crossing all of them. Ric Flair may indeed be the one responsible for their attitude, but they all strived to be the best — a fact proven when Flair, Arn Anderson, Tully Blanchard and Barry Windham held every major NWA title much to chagrin of fans and competitors alike. — K.P.

1

"Rowdy" Roddy Piper

Shock doesn’t age well. Things that once outraged the public — Howard Stern, tattoos, Chubby Checker’s “The Twist” — seem downright family friendly today. The years have not had this effect on the crimes of “Rowdy” Roddy Piper.

The key antagonist in Hulk Hogan’s rise to pop culture ubiquity in the mid-80s, Piper and Paul Orndorff headlined the inaugural WrestleMania against The Hulkster and Mr. T. But "Hot Rod" was at his worst against defenseless victims. As the incendiary host of his “Piper’s Pit” talk show, he enraged audiences and incited guests long before Jerry Springer was a household name. During his unpredictable segment, The Rowdy Scot forcefully clipped the hair of little person grappler The Haiti Kid and, most infamously, cracked a coconut over Jimmy Snuka’s head and then smushed a banana in Superfly’s maw.

Three decades removed and WWE fans are still shocked by Piper’s actions. Few other villains can say the same. — R.M.