Over the years, the business of being an effective heel has changed. The heel's character and story type has evolved as the art of wrestling has evolved. And it has developed as the audience's expectations have developed. But one characteristic of a heel has always remained the same: a heel's defeat must always be believable and noteworthy. The villain must draw the crowd into his story before he ultimately falls to the hero in dramatic fashion. Of course, that defeat may not come right away, but it will come eventually.

It's not easy being a villain. In fact, one might question whether it's truly harder to be a villain than to play a "face." And it's a reasonable question. Not only does a villain have to welcome the hatred that inevitably surrounds him like a thick fog, but he must handle immense public pressure whenever he saunters to the squared circle. To further analyze whether or not it's more difficult to be a villain or a "face," we might ask, what is a more powerful emotion, love or hate? Is it is easier to be loved or hated? Is it easier to stay in character when fans are cheering or booing you? Maybe the answers to these questions all depend on the wrestler.

The wrestlers listed here all succeeded where many failed. They not only became an effective heel, they developed into the greatest villains of them all. The audience believed in their characters, their motives, and their ability to carry out those motives over their opponents. Further, these villains helped advance the wrestling business. They helped create the nWo, D-Generation X (if you want to call them villains), The Attitude Era, and every group and individual between. You love to hate them and you hate to love them. The following are the greatest wrestling heels of all time.

25 25. Stone Cold Steve Austin

No one expected Stone Cold to align with the McMahon regime, especially after the their years of fighting each other. However, when Stone Cold finally shook Vince McMahon's hand, it rocked the wrestling world. Fans didn't like it and even Austin had some initial reservations, but every week fans tuned in likely to see if Stone Cold had come to his senses. His stint as a heel was short, but memorable.

24 24. Chris Jericho

He entered the WWE impetuous, cocky and often comical, engaging in classic verbal wars with some of the company's legendary characters. He mocked them and their fans. As his career evolved, Jericho put away the fancy clothes for more standard pin-up suits and sported a shorter haircut to go along with a more serious personality. However, when he first entered the WWE, not many other wrestlers could rile up the crowd like he could.

23 23. Scott Steiner

Steiner's career took off when he betrayed his brother Rick as they defended the Unified WCW Tag Team Championship. From there he morphed into Big Poppa Pump and a powerhouse, capturing the United States Championships, two Television Championships, and the WCW World Title. He was arrogant and aggressive and he made sure people knew it. It's too bad that as he became Big Poppa Pump, his wrestling skills also deteriorated.

22 22. Andre the Giant

He's an icon and forever immortalized as one of the most popular wrestlers in history. However, there was a time when The Giant became the most hated superstar in the business. In 1987, he ripped off the cross from the neck of long-time friend Hulk Hogan, which suddenly ended their friendship. The two would later battle in a match for the history books, which marked the end to The Giant's long, unbeaten streak. The match would help propel the career of another "face" turned heel, Hulk Hogan.

21 21. Edge

After his original group, The Brood, disbanded and his tag-team with Christian dissolved, Edge set off on a singles career. He capitalized on his opportunities and quickly became a superstar and villain in the WWE, cashing in his World Title contract to snatch the WWE Championship from John Cena at New Years Revolution 2006. His relationship with Vickie Guerrero was nothing more than a ploy to advance his career. The crowd knew it too, and they detested him for it. On top of that, his somewhat non-fictional feud with Matt Hardy and Lita really drew the ire of the crowd.

20 20. Randy Orton

Orton made his name in the WWE by taking out legends like Shawn Michaels, Sgt. Slaughter, Ric Flair, Mick Foley, and others. While he turned "face" in the late 2000's, Orton is best known for his vicious, often sudden attacks, using his signature RKO and Punt Kick finishers to literally finish off opponents. Recently he turned heel again, which seems a better fit for The Viper. He also was a part of Evolution, a heel stable, which has 3 members on this list.

19 19. The Dudley Boyz

Tables. Tables and more tables. While the team built its resume without the weapon, their use of tables helped define their characters. In May 1999, The Dudley Boyz lit their first table on fire and power bombed Balls Mahoney through the igniting piece of wood. They knew how to antagonize the audience and continued to do so when they moved into the WWE where they fought in the first ever TLC match with Edge and Christian and The Hardy Boyz. 

18 18. Jake "The Snake" Roberts

Roberts was one of the WWE's most psychologically menacing foes, using fear hidden away in burlap sack to keep opponents on edge. When he won a match, it was not surprising to see a giant python, or a cobra, spill out of the sack and onto the ring, or worse, the opponent. Roberts almost ended the career of fan favorite Ricky "The Dragon" Steamboat and allowed a Cobra to snack on a helpless Randy Savage as he was tied to the ring.

17 17. Kane

Unlike his brother The Undertaker, who some may view as more of an anti-hero, Kane is undoubtedly a pure villain. He's been always cast as the psychologically unstable half-brother of The Phenom who set his half-brother on fire, electrocuted Vince McMahon and caused harm to countless other wrestlers. Even when Corporate Kane emerged in more recent times, he's still as unstable as ever. The suit can't contain the beast within, and more than once he's attacked other wrestlers, which some may view as slightly unprofessional. However, they'd likely never say that to Kane.

16 16. Sgt. Slaughter

While he's revered today, Slaughter was once one of the most hated men in wrestling. His brutal assaults on WWE Champion Bob Buckland, when the former first joined the company in 1980, are famous. Although Sgt. Slaughter was pro-American, he became instantly hated in 1991 when he showed sympathy for Iraq. At the time, America was still neck deep in the Persian Gulf war.

15 15. C.M. Punk

The WWE universe wants Punk to return and for good reason. His matches are epic, his speeches mesmerizing and his influence on the WWE universe iconic. In fact, this power over the wrestling business helped make Punk into a tremendous villain. He formed the Straight Edge Society, pestered and beat Rey Mysterio in front of his family, and mocked Jerry Lawler for his heart attack, to name a few.

14 14. Rick Rude

You don't have the last name "Rude" and then become a "face" in the WWE. Rude only strolled down the ramp and to the ring for two reasons: One, to verbally beat down the crowd and two, to physically beat down his opponents. He first demanded the crowd be silent as he disrobed to reveal his attire, which was often airbrushed with his smirking face or the faces of his opponents. He then ruthlessly attacked opponents.

13 13. The Million Dollar Man

How wicked and crooked was The Million Dollar Man? Let the stories do the telling. He was the Scrooge of the WWE, barking orders at his manservant Virgil, tricking children into believing they could win $500, and stuffing $100 bills into the mouths of his opponents. Perhaps his greatest investment was in a another villain on our list, The Undertaker, who debuted as the fourth man in The Million Dollar Man's 1990 Survivor Series Squad.

12 12. The Undertaker

The Phenom battled countless "faces" over his three decade run in the industry. From Hulk Hogan to Mankind to Steve Austin and every "face" in between, The Undertaker  knew who to target to rise from ashes to stardom. He invented the casket match, threw Mankind off a 20-foot cage, and was the creator of the Ministry of Darkness. His greatest heel moment was when he kidnapped Stephanie McMahon and then forced her to marry him so that he could control the entire WWE. Pretty sadistic...

11 11. Randy Savage

While everyone now respects Savage for his years of work, few appreciated his heinous actions during his heyday. He was the WWE's top villain and often fought against some of the company's hero figures like The Ultimate Warrior and Hulk Hogan. Savage eventually donned the name "Macho King" and his legend continued to grow. He eventually moved onto the WCW and the nWo, which further added to his legacy as a great heel.

10 10. Paul Heyman

"Ladies and gentlemen, my name is Paul Heyman."

He is arrogant and brash and not afraid to upend the status quo. In recent years, Heyman has been one of the WWE's most annoying antagonists and recently further solidified his renowned status as a heel by managing another heel, Brock Lesnar, "the beast incarnate" who ended The Undertaker's 21-0 streak at WrestleMania 30. He knows how unhappy we are about it and he'll never let us forget it.

9 9. Bobby Heenan

Before Paul Heyman had his "Paul Heyman guys," Bobby Heenan had his "Heenan Family." Bobby "The Brain" Heenan was the original, notorious manager who ran his mouth on his client's behalf. Some of his clients were the greatest villains of them all and are well represented on this list. He manged several wrestlers who made this list like Ravishing Rick Rude, Ric Flair and Ted DiBiase.

8 8. Triple H

Triple H took a long, hard road to wrestling prominence, but when he finally made it to the top, he did so as a heel. Whether it was battling The Rock, Stone Cold or countless other victims, Triple H made each match and beat down count, and made especially sure to use his trusted sledgehammer whenever he could. However, his reign as a heel hasn't stopped there. Currently acting as the company's COO, Triple H has redefined himself as a three-dimensional heel, one who simply doesn't hate wrestlers for the sake of hating them, but instead because it's "best for business."

7 7. Hulk Hogan and the New World Order

When Stone Cold aligned himself with Vince McMahon it shook the wrestling world. But when Hogan turned rogue and formed the New World Order with heels Kevin Nash and Scott Hall, he brought the world he once created crashing down. As part of nWo, a ruthless group that showed no mercy on its opponents, Hogan was arrogant, vicious and uncaring. He reinvented himself as one of the most dominant heels in the history of any wrestling industry.

6 6. Vince McMahon and His Family

Vince McMahon is the ultimate heel for one reason and one reason only: he cared only about himself. McMahon wanted to step on the toes of others to put them in their place. And, of course, in the process make himself look better. He sacrificed his daughter, battled his son and orchestrated the notorious "Montreal Screw job." You may even call him a heel behind the scenes. He refused to pay top dollar for WCW's main talent when his company bought out the Atlanta-based company, which aided in destroying any chance the WCW could merge successfully with the WWE.

The apple doesn't fall from the tree, as evidenced with Stephanie McMahon and he role in the WWE. As a current member of the authority, she is one of the more annoying and despised characters in the WWE right now.