Top 5 Favorite Heels of All Time

Personally, I have always found the heel character (tweeners as well) to be more interesting and entertaining than the "good guy" face wrestler, so I thought it might be fun to see who others on this forum consider their personal favorite "bad guys." Name, and give reasons for, your top five favorite heel wrestlers of all time, from WWE/WWF, WCW, ECW, TNA, or any other promotion you may prefer.

My List:

5. Randy Orton- I know I am probably going to get hammered for this, "so sue me." Do I think he ranks among the top heels of all time? No (not yet). But he is definitely one of my favorites from this past decade. He is an old school type heel, a complete character. He is evil, cruel, and, at times, downright insane. I think over the past 2 years, he has improved dramatically. Physically, he no longer looks like a soft kid out there, so he is much more convincing as a top level heel. In the ring, he looks demented. He really makes you believe he is hurting his opponent (sometimes, he might be) with how well he tells that story during the match. His mic skills are great as well. He is a good actor, and that is a big part of entertaining the fans (it's not all about in ring ability or big spots). While a lot people were upset with how his feud with HHH ended last year at Mania, those two, along with the McMahon family, had the most heated, personal rivalry in years. It was great storytelling, and that angle helped make him, in my opinion, the top heel working today.

4. Hollywood Hulk Hogan- It pains me to say it (never was a big Hogan fan), but he was a great heel. His heel turn at Bash at the Beach '96 was the biggest (and most well done) thing in wrestling. No one ever expected this guy to turn heel, and when he did, it shocked wrestling fans everywhere (if you don't believe me, check out the crowd reaction after it all went down). In the ring, Hogan was never any good, but he could tell a story like no one else, and it never came off as well as when he was WCW's top heel. He made up for a lack of in ring talent by entertaining the crowd with his over the top antics and gimmicks. On the mic, he always knew the right buttons to push (on the crowd). He knew how to draw cheap heat better than anyone in the business, and it was pretty entertaining to watch (much more so than his Red and Yellow garbage).

3. Ravishing Rick Rude- From WWF, to WCW, this guy had it all. He was super talented in the ring, with unlimited athleticism. He could put on a 2 minute squash match or a 40 minute battle, and either one would come off entertaining. He was great on the mic as well, calling everyone sweat hogs and telling the women in the audience to "see what a real man looks like." This guy was born to be a heel, with that cocky, arrogant attitude that everyone remembers. He never reached the heights in WWF that he did in WCW, which is unfortunate, because WWF was so much bigger at that time, he didn't shine nearly as much as he should have. I believe nagging injuries and such kept him from being one of the two or three greatest heels in the history of professional wrestling.

2. The Million Dollar Man Ted DiBiase- This guy was hilarious. HIm purchasing the WWF title from Andre the Giant has to be one of the greatest moments ever (not for poor Andre). That was the perfect way for him to get the belt (too bad they took it away from him before it could count as a title gain). But him never being a WWF champion doesn't bother me, because I think he was one of those guys who didn't need a title to get over. He had a great, slow paced offense in the ring, and not many people sold better than him. He was top notch on the mic, with the ability to draw heat without actually insulting the crowd. His gimmick with Virgil was pretty racist, and it wouldn't stand today, but those guys played very well of off one another. While I don't believe he needed the WWF title, I wish he had won it, at least once (almost did in an amazing match with Savage at Mania 4).

1. Ric Flair- Greatest heel of all time. He did it like no one else for 30+ years. He had feuds with Harley Race, Dusty Rhodes, Randy Savage, Sting, Hulk Hogan, Ricky Steamboat, and many, many more. There has never been a guy who could get a face over as well as he did. He could help make anyone a beloved star just by being in the ring with them. I have always thought his best attribute was his ablity to sell. No heel in the history of pro wrestling has been able to sell a beating like Flair. He wasn't just called the dirtiest player in the game, he WAS the dirtiest player in the game. But this guy was no sloach in the ring. He could go 30 minutes no problem with just about anyone, and make it look great. He was the figure-head of the greatest heel faction in the history of wrestling, the Four Horsemen. I could go on for pages about this guy and what he did for the role of the heel in pro wrestling, but I won't. In my opinion, he was the best and no one has come close to him.
 
5. Edge: There's just something about Edge that makes him such an amazing heel, he really knows how to work the crowd, and he can run the mic very well when it comes to getting boo'd.
Also looking back at his long feud with Cena, it really elevated Edge into the main event picture, and he's stuck around ever since, I personally wouldn't want to see Edge as a face, because he works so greatly as a heel, hence nr 5.

4. randy Orton: Randy is just awesome as a heel, just as Edge he knows how to get the crowd to hate him, he knows how to get an reaction out of the crowd, especially the weeks before wrestlemania 25, me being a complete mark around that time, I really got to hate the character Randy orton, and since then, knowing it was just a character and everything, I've realised how awesome a job he is doing as a heel.

3. Ric flair: He could it all, he could work the mic like noone else, and knowing how to work the crowd, his dirty in-ring moves and everything, it really classified him as the perfect heel, seeing some of the promo's he cut on people in the WCW NWA and the original NWA concentrating alot on being custom made, which really solified him as a self centeret heel, showing respect to the opponents but not being too shy on dissing them.

2. Chris Jericho: Chris is a full born heel, whether he's getting cheered, or getting boo'd by the crowd as a heel, he knew how to draw a reaction from the crowd, also once reading a interview he made, where he mentioned that he stopped with all his y2j things and the fun loving heel, because he felt he wasn't doing a great job as being heel if he was getting cheered, which really made me give him alot of respect for what he's doing, working the mic perfectly, working the crowd in matches with his constant taunts and his slaps to the back of the head, the occasional Codebreaker that he would bust on opponents that just beat him, or as a final beatdown to a just beaten opponent, in this case the moment that really made a lasting impression for me was the time he, Edge and Ziggler assaulted Rey Mysterio.

1. Triple H: really.. who else is there to put in number 1 than triple H? yes I know Nick put Ric Flair as number 1, but to me Triple H is the greatest heel of all time, his work in the late 90's both in DX and in the Mcmahon-Helmsley faction/era to the time in Evolution with the constant beatdown of enemies, the cheating to win, the sledgehammer to the head of Shawn Michaels, the title-reigns.. everything about Triple H screamed the one and only!
Triple H's way of complaining when he got mixed into a match with someone like Rikishi, The Rock and Stone Cold in the 99-00's standing in the ring and someone like Vince od Foley announcing it, it was awesome, and I truely miss this Triple H, and hope he makes a return eventually, cause his heel character was.. "that damn good"
 
Y'all are so young. You really are.

5. Bobby Heenan. Managers often make the best heels. Heenan, much the same way JJ Dillon did in the territory system, became the quintessential heel manager. He got the faces he opposed over HUGE. Virtually everybody under the sun wanted to see Hogan, Warrior, et als get their hands on Heenen for just a moment. You wanna talk about heat? When he helped Rick Rude defeat the unstoppable Ultimate Warrior for the Intercontinental Title. THAT was heat!

4. Big Van Vader. Damn right. He opposed Sting very respectfully after Flair went to WWF in the early 90's. Him and Harley Race were dominating as a pair, beating fan faves such as Sting, British Bulldog, Ron Simmons, and Cactus Jack. Vader was not only sadistic and borderline evil, he was also terrifying and could back everything up in the ring. Even internationally. When Vader beat Inoki in under 3 minutes in Japan, Vader's debut, a riot ensued.

3. Tully Blanchard. The guy was a master. A fantastic worker. He understood what a heel's job was better than almost anybody - be a good worker and get the face over - not yourself. Tully was a phenominal NWA National Champion. With JJ Dillon as his manager and Baby Doll as his valet, Tully was the embodiment of what everybody hated - good looking, successful, surrounded by powerful people, and in your face better than YOU.

2. Shawn Michaels. In the early 90's, Shawn was an amazing heel. He was, like Tully, everything you hated. He turned on his best friend, became brash and arrogant, carried a mirror everywhere he went, ran away when he could, had a valet with a shrill voice, and yet somehow always managed to come away seeming like a winner, even in being a coward. He put guys over left and right - Marty Jannetty, Crush, Tatanka, even Doink the f'ing Clown got face pops when he faced Shawn. As great as Shawn was as a face, he was even better as a heel.

1. Ted DiBiase Sr. Brilliant heel. He never held the WWF Title, and never needed to. People DESPISED this guy because he had loads of money, and used it to get what he wanted. Plus, he opposed the working class guys like Dusty Rhodes, and was a decent anti-hero for Hulk Hogan. The relationship DiBiase had with Andre is similar to what Shawn did later on down the line with Diesel and Sid.
 
Y'all are so young. You really are.

I think I'm fairly excused being 17 (nearly 18) and only having watched WWE for 1 year ;p

But yeah, your list is pretty good, I just personally didn't think Shawn Michaels fitted into my list so much because he's gone for quite a while as a face guy, and sure he had some great heel characteristics in the 90's especially with his funny stuff with DX, but I just felt he didn't fit into my list :)
 
I think I'm fairly excused being 17 (nearly 18) and only having watched WWE for 1 year ;p

But yeah, your list is pretty good, I just personally didn't think Shawn Michaels fitted into my list so much because he's gone for quite a while as a face guy, and sure he had some great heel characteristics in the 90's especially with his funny stuff with DX, but I just felt he didn't fit into my list :)

Hahaha, it's ok. I am just always amazed by the lack of old school representation on some of these lists. It's just a curse of the IWC - people think pro wrestling started with the Attitude Era.

Anyone who didn't experience Shawn Michaels in the early 90's, immediately following the breakup of the Rockers and up to this WM13 Title win, missed out on one of the great heels of the era. And LONG LONG LONG before the DX vs Hart Foundation and Screwjob controversies, Hart vs Michaels was a rivalry between two young studs who were poised to rule the WWF. One Survivor Series main event saw a half-hour match between WWF Champion Hart vs IC Champion Michaels. It was truly one of their best matches ever.
 
Hahaha, it's ok. I am just always amazed by the lack of old school representation on some of these lists. It's just a curse of the IWC - people think pro wrestling started with the Attitude Era.

Ofcourse it didn't ;p as I noted in my list when I listed Ric Flair I took the time to view some of his promo's in the 80's which I really enjoyed, but I must indeed admit I'm far behind on my old school 70-80 wrestling knowledge if the person wasn't a big name in the mid-end 90's and in the 00's which is where my knowledge lies the most.

But about the Shawn Michaels part, I did watch some of the start 90's thing with him, he did indeed stand out as an amazing heel and very cocky character, the whole bodyguard angle, the sherri thing completely dominating her in a kind of S&M kind of relationship, but with a fun twist to it. Shawn has always been a great wrestler to me, but the only time I really enjoyed him as a heel was when he was doing fun heel stuff in DX, anyelse Shawn works best as a face.
 
5. Rick Rude- The removal of his robe at the beginning of his matches and the ensuing promos were the stuff legends were made of. Then his tights were heat machines all in themselves. Jake Roberts wife on his tights? The IC strap on his tights before he won it? Just insane and heel godly!

4. Hollywood Hogan- Man for every bit as I was a Hulkamaniac back in the day, I hated him that much as Hollywood. I liked the nWo but I just hated, absolutely hated Hollywood and he was great at it. Slapping people, chicken shitting out, having his goons beat people up for him and bsing his way into keepin the strap and his ego, good lord he just played himself so well.

3. Ric Flair- THE epitome of what a heel was. The founder of the greatest faction ever. That's all that needs to be said.

2. HBK- holy shit was HBK godly as a heel. He was always a strong heel in his first heel run, but his 97 DX run is just amazing. No one was better on the stic at the time than HBK and his DX skits were revolutionary and I really hope he gets another heel run when DX breaks up this time around because he was totally awesome during his 2005 1 month heel run against Hogan.

1. Jake Roberts- Nobody today can even come close to matching this dudes psychology or intensity in promos. Jake was the absolute darkest heel I ever met and as a child he came closest to scaring me than any wrestler ever. His feud with Randy Savage is perhaps the best heeling the business has ever seen. He slaps Elizabeth, which was the first time that had been done in WWE, beats the ever loving shit out of Randy many a times and then he HAS A FUCKIN COBRA BITE Randy! To top it off, after Randy won the blow off match he still laid him out with two DDTs and leaned over and yelled at a an unconscious Savage and screaming at Liz that it was "her damn fault". Just sickness that blows away all the lameness of WWE's modern heels. I think Orton's attacks on the McMahons were molded after Jake. If you really want to see what a heel is supposed to be go youtube some of this stuff. Still miles ahead of the garbage TNA and WWE is peddling these days.
 
5. Macho Man Randy Savage-this guy could pull a heel or face character off well. I liked him much better as a heel than face, his fued with Hogan was great, but I still felt he deserved to beat Hogan AT LEAST once.

4. Demolition-My all time favorite tag team. Loved it when they beat Strike Froce for the belts at WM IV, Chico Santana got on my nerves!

3. Million Dollar Man-My favorite was when he tried to buy the belt and when he purchased number 30 for the Rumble from Slick, then comes back the next year with #1 and last through much of the Rumble.

2. Ravishing Rick Rude-My 2nd favorite wrestler of all time. I can't tell you how much I appeciated him for beating the Ultimate Douchebag for the IC strap at WM 5. I only wish he could have won the World Strap from him at SS 90.

1. Hollywood Hulk Hogan-I loved him through think and thin and loving him at a time when everyone hated him was special for me. Once at a WCW PPV there were only 3 Hogan fans on the side that I sat, I was one of them!
 
IC25 wants old school. I will give him old school.


5. "Nature Boy" Buddy Rogers:
Talk about flamboyant, talk about getting under the crowds skin. this guy could do it. He would go on and cheat to win, then get on the microphone and say "To a nicer guy, it couldn't have happened". He would also go and take advantage of his opponent. The crowd thinking it was real at the time ate it up, and he got booed even more.

4. Larry Zbyszko: Started off as a face, as the student of ultra babyface Bruno Sammartino. After almost a decade, Larry decided he wanted out of Bruno's shadow, and decided to challenge him to a match. Bruno accepted and then the turn came. He left Sammartino bloody. The student turned on his teacher, and one of the best heels was born.

3. The Sheik: Just one crazy motherfucker. Seriously. He would throw fireballs at his opponents, and not only that, when he was out on the streets, he would do it to fans that approached him to preserve his character. His style of wrestling was also mundane, hold after hold. Refusing to break them. This man knew how to be a heel.

2. Tully Blanchard: Everything that IC25 said and ten fold. He just knew what was up. Making his opponent look good. His promo work. Just everything about him oozed evil. Can't say much more than this.

1: "Classy" Freddie Blassie: "You pencil necked geeks!" The phrase everyone used to hear, and everyone used to hate. Whether he was wrestling or he was just managing. The fans loved to hate the shit out of this guy. He can probably be attributed to the way today's heels are. He was so hated at one point, that the fans couldn't hate him anymore, and started to cheer him when he was a wrestler, then he turned into a manager, and the rest is history.
 
I'd say these guys are my top 5 favorites:

1) Michael Hayes : The leader of the "Boy's from Badstreet" got so much heat that it was off the charts ! He had the fans of the Von Erich's as well as JYD wanting to kill him ! One of the best promo guys ever !

2) Tully Blanchard : So cocky and he just came off so smug that you couldn't help but hate him. Great talker and worker and had a classic feud with Magnum T.A. and I thought bought out the best in Dusty !

3) Roddy Piper : What a talker and the guy who really helped make the first Mania a success !

4) Gino Hernandez : Like Blanchard, his former partner, just a great natural heel ! So cocky and hateable the guy was made for wrestling and could never be taken seriously as a face !

5) Ric Flair : The total package as a heel from the look, promo's and cockyness !
 
5. "The Nature Boy" Ric Flair
This guy is amazing, and he can get the crowd to hate him easily. Even in todays world where fans will cheer a wrestler who's a heel just because he's wrestled for 12 plus years.

4. Kurt Angle
In this business there's a few people who can only play one alignment. Sure, Angle has done the face roll before, but let's face it you guys... We all love to boo Kurt Angle. Whether it was with the "You Suck" chants started by the Rated R superstar himself or if it was with his run as TNA Champion, wrestling fans have always hated Kurt Angle.

3. Vince McMahon
So he's not exactly a wrestler... But he IS a heel, and quite frankly, the biggest one of all time. If he's a face, he isn't one for long. Vince is just that good at getting us to hate him.

2. Curt Hennig
Along with Rick Rude, these two made being a heel so fun. They always went out there and talked about their good looks or their superior wrestling abilities. Sadly though, neither of them went on to be the top champion they should've been.

1. Shawn Michaels
He isn't given the roll a lot, but when he does, he brings his A-Game like never before. From the times he was with Scary Sherry to the Commissioner of the Corporation, HBK is without a shadow of a doubt the most charismatic heel of all time.
 
5. Ric Flair - Flair was cocky, brash and charismatic and he did it all with such style. He cheated his way through countless title reigns in an era when cheating was neither cool nor funny. Flair new how to draw heat yet entertain the audience at the same same. Flair was the NWA back in the 1980's. He was their top draw and he did it as a heel. Now that's good work.

4. The Dudley Boys - Anyone who didn't have the opportunity to see these guy perform back in the ECW in the mid 1990's is really missing something special. They cut promos that made your jaw drop. ECW had to stop the show on a few occasions because the Dudley's had incited a near riot. They created so much heat that it was uncomfortable to watch at times. They were no holds barred, say what you feel, badd ass guys who worked the role of a heel like nobody's business.

3. Jake Roberts - I couldn't decide whether Jake Roberts or Raven should be #3 on this list because in my eyes they are cut from the same cloth. Masters of the heel psychology. However, Roberts did it first. Back in the 1980's almost all promo consisted of yelling in your "I'm a wrestler" voice. Jake Roberts attacked a promo with a new and refreshing approach. He spoke calmly in a quiet and creepy tone. He evoked emotion and he made you believe that he might just be evil.

2. Roddy Piper - He was innovative before you were allowed to be innovative in the wrestling business. The Piper's Pit segment with Jimmy Snuka will forever be burned in my mind. It was absolutely amazing and just a glimpse of what Piper was all about. He was a tremendous talent who could generate heat at the snap of a finger. This guy was so successful as a heel, he never needed to win a major championship. He was already over.

1. Shane Douglas - The Franchise. Say what you will about his attitude- it got him fired from WCW and the WWF. So what? Shane Douglas took that attitude and made himself into the greatest heel this business has ever seen. Shane was able to generate obnoxious amounts of heat. I'm talking about white heat. The kind where he had to be snuck out of arenas because fans wanted to kill him. Shane spoke from the heart and said things that pissed off alot of people and he disgraced the NWA belt (hey, he didn't mean a hell of alot by that time anyway). An amazing performer who delivered beyond expectations each and every time he stepped into the ring.
 
5. Mr. Perfect: Just a jerk you wanted to see get beat, but was so darn good. I equate him to a villian jock in a high school movie that always has a smirk on his face chewing gum like a goon.

4. Hollywood Hogan: What I thought was great about Hollwood was that a lot of guys turn for no reason, but he had more than enoug fodder to have it all make sense. His turn seemed only natural after years of the fans begin sick of his old gimmick. He didn't become someone else- he became an older, insecure, over fed and bloated meglomaniac-a natural progression for anyone in his position.

3. Ric Flair: There are only two reasons that he isn't farther down the list. (1)He was just too darn cool for my money as a heel(2) He is clearly overcompensating in my opinion for a loss of confidence now. This has resulted in Flair going from a cool customer to too much of a raving lunatic. You might call it reinvention, but I don't see it that way. I still love him though

2. Rick Rude: I think that Ruck Rude would have been just fine with the same exact gimmick right this very moment in time. He was darn cool too, but just rotten enough to wanna see him get his. I think he should've had a run with the title and would have if this was like 6 years later than he was on top. I also think Hogan/Rude would have been really cool. One of my faves, so maybe that's why he is so low on the list.

1. Piper: You just hated his guts, but not in the way you don't like say, a Bubba. You really did love to hate him. His mouth was dangerous, and even in the last several years he has come out with some great stuff.
 
5. Triple H
When he was a heel, By god you knew it. Everyone loved hating him. From his feuds with Shawn Michaels to Ric Flair, to being the leader in the heel group, Evolution, Triple H was a good heel. He also had moments where he wanted to make you punch your TV and curse him out. Such as, attacking HBK in a parking lot, or when he turned on Shawn during that supposed "DX Reunion" back in 2002.

4. Ted Dibiase
A cocky, arrogant man who was better than you just because he had money. A heel for pretty much his entire career. He had many moments that made you want to knock his teeth out. There was the infamous "Dribble the basketball 15 times" Incident. He hired fan favorite, Andre The Giant to win him the WWF Title. Ended up creating tag teams that made you mad at times too. Anybody remember Money Inc.?

3. Ric Flair
He's called "The Dirtiest Player In The Game" for a reason. That's because when he wasnt cheating his way to a victory in the ring, he was most likely managing a superstar. Ric was a part of Evolution, a mega heel stable. In Evolution he was the man that every fan loved to hate. But even before that, like his times as world champion, where he was a cocky son of a gun. Ric was THE heel to beat during his time.

2. Hollywood Hulk Hogan
I remember him standing in the middle of the WCW ring with fans throwing trash into the ring, when Hogan said those infamous words, "You fans can stick it, Brother!" I was pretty pissed off when that had happened. From that point forward, Hollywood Hogan established himself as a mega heel with the nWo. He contributed to the collapse of a company! Even when he and the nWo jumped ship to the WWE, he was a mega heel. Anyone remember when he and the nWo brutally attacked The Rock after Rock challenged Hogan to a match at Wrestlemania? He god damn almost killed the man! Hogan was a great heel.

1. Vince McMahon
Could've seen this one coming. Ever since the infamous Montreal Screwjob, which pretty much cemented himself as the biggest heel of all time, he would go around screwing other superstars. There was the feud with Steve Austin that everyone remembers oh so well. There was his feud with Bobby Lashley, where he kept screwing him out of the ECW title. There was also the feud with DX, where he tried to destroy them. Simply put, he is the boss, and at the end of the day, if you were to face him in a match, you are probably going to end up losing. Why? Because he IS the term "Heel."
 
5. Raven
This guy always creeped me out for some reason he cut scary promos and always had a bunch of dudes with him that would protect him by any means.

4.William Regal
This guy made you hate him just for the fact that he was english. whether he was kissing McMahons ass bring the commissoner of Raw or Being an unamerican he got under everyones skin

3. Curt Hennig/ Kurt Angle
These two tie for me Hennig played the heel role perfectly from his time in the AWA WWE and WCW. As for Angle the you suck chants say it all the fans had a passionate hate for him

2. Roddy Piper
Whatever this guy said pissed people off. He always knew the right way to insult his opponent and was quite funny while doing it.

1. nWo
These guys had no respect for anything they ran through WCW kicking ass and taking names. They always kept things between them too which i liked because they ran it like a street gang and it was quite interesting to say the least lol.
 
5. Ted DiBiase- The Million Dollar Man- The name says it all. You hated him for everything he was, rich, talented, handsome (I think so.), and he could get anything he wanted. He even passed this on to his namesake now!! You gotta admit, getting fans to do whatever he wanted, just for mere dollars. The most heinous thing I remember was offering that little kid I think $500 dollars if he could dribble the ball 15 times. By the 13th time, he kicked it away from him, and the kid was in tears!! That is a CLASSIC heel. LOVE HIM!! :worship:

4. Jeff Jarrett- Dude, when I first started watching TNA, I truly hated this man with all my heart. I truly despised everything he did. I watched old clips of him from my hubby's classic WWE shows, and even then he seemed like a prick. The lengths he went to just to keep his belt no matter what organization, but mostly TNA, it was heinous. The splashing of gasoline in Sting's eyes. :wtf: I was so in shock. Having someone secretly videotape Sting's family, that was very cruel. But, I slowly started to love the JJ. Rock on!! :headbanger:

3. Lita- I admit, I LOVED her as team extreme. Then when Matt turned on her, I was shocked. Then she was with Kane. I was shocked when she turned on him with Edge. :wtf: But I was interested to see where it went. Then you add Matt with his craziness and the real life luv triangle. Then it just went on from there. She was kick ass with her attitude. I loved how she could keep torturing him, and women in the division. Then the LIVE SEX show with Edge!! double :wtf: . It just sucked how they sent her out though.

2. Edge- A list wouldn't be complete without him since I brought up Lita. This man will slap Cena's dad. Have a live luv fest in the ring. He will beat the living snot outta wwe legends with no regrets. He hosted the Cutting Edge to make fun of Ric Flair after Flair's arrest for Road Rage. That was pure ballsy. He certainly is NOT afraid to call people out on their little inner demons.

1. Randy Orton- This list wouldn't be complete without him. A man who will RKO old women. He will set people on fire in locked caskets. He runs over them in a car with his dad. He will RKO his gf's on the tv. Starting the streak of punting people out of their tv runs. Then to systematically take out the ENTIRE McMahon family on live tv. Of all, the most vile, to handcuff HHH, and assault his wife in front of him, and then kiss her while unconcious. I truly do think that nothing can ever top that sickening moment.
 
Here's a pop:

5: Vader: This guy was hated everywhere he went. He was hated in Japan, WCW, WWF. He attacked Inoki post a match that Inoki had taken a beating in and the fans hated him for it. He attacked Sting in WCW as well as others like Cactus Jack and Davey Boy Smith, HBK in WWF as well as Gorilla Monsoon. He was despised for beating up the popular guys and leaving them there laying. Nasty guy.

4: The Rock: Cast your minds back to Survivor Series 1998. How hated was the Rock when he slapped on the sharpshooter to win his first WWF Championship? He was booed until the cows came home. Prior to that you had the Nation Rock as well as The 'Die rocky Die' chants which were nasty as hell. Afterwards we saw the Rock go face for 3 years only to finally turn into Hollwood Rock which was my personal favourite run with The Rock. His promos on Hogan, Austin and Goldberg were all very entertaining as well as the ones he did on The Hurricane. Great heel.

3: Chris Jericho: This man knows how to get people to hate him and he can exploit it. In 1999 he interupted The Rock, that lead to heat. In 2001 he grew an ego out of winning a world title. He became dispised and it lasted for 3 years. In that three years he became Undisputed Champion, attacked his idol Shawn mcihaels and just about launched an anti-Austin campaign. It was in 2008 though when he may have truly become the great heel he is today when he threw HBK into the Jeritron. It was a great turn and slowly he became HATED. But was he punished? Nope, he's won three world titles since then as well as become a record breaking Intercontinental champion and the longest reigning Unified Tag team Champion in history. He's become great.

2: Bobby 'The Brain' Heenan: 'Weasel, Weasel.' Those chants will forever live in the hearts of wrestling fans around the world. This man could get anyone over. This man was the man who made Andre the most hated man in wrestling. This guy was responsible for getting so amny people over it isn't funny. he would sell for The Ultimate Warrior and make Ric Flair WWF Champion. And the fans hated it because the fact was, he backed up what he said. He gave people champions like Mr. Perfect, Andre the Giant and Ric Flair. He truly was hated.

and number one is:

1: 'Million Dollar Man' Ted DiBiase: 'Everybody has a price' is possibly the greatest catchphrase in wrestling history. The fact is DiBiase has the power to make you look great. he was another who helped the Ultimate Warrior. he was hated for trying to buy the WWF Championship, hated for treating Virgil the way he did, hated for being so good at what he did. So when the tables turned against him, the fans would love it. It was great. Ted DiBiase was and is the greatest heel of all time in my opinion.

EDIT: Here's basically a highlight reel of Ted DiBiase in a pre-match interview: http://www.youtube.com/watch?v=td9i6-oa4Kw
 
5. Batista-He's great as a bad guy and a great performer. His run as a bad guy against John Cena I just wish they would come up with a cooler storyline than who's better.

4. HHH-He's so believable. Him & Stephanie had great chemisty together. After Evoloution though he had nothing going for him so good thing they brought back DX.

3. Undertaker-He seemed so much more evil as a heel. I think if they turned him back as a heel to face HHH or something it's be great.

2 Edge- This guy just looks like a mental person when you look at him. As a heel he's got this great thing going as the master of the mind or the ultimate psycholigist. Plus he won his world championships as a heel so theres no reason to turn back.

1.Ric Flair-Woooooooooooo! There is no one worst than the dirtiest player in the game. I don't really even need to explain this one.
 
5: Hogan, I have to say this cuz at the time his heel turn was so dramatic and almost unexpected. It made some people love or loath him. He was great at drawing heat during his nWo days.

4: HHH from DX/Stephanie to Evolution His heel status made memorable feuds with Rock, Austin, Undertaker and helped boost Jericho to upper-main event status. Along with some very memorable Jeri-quotes. HHH was so much more evil and conniving as a heel. Like trapping the Rock in a casket and sledgehammering the crap out of it in 99.. spectacular

3: Owen Hart: as a child I loved to hate Owen cuz he was so whiny and cunning. Especually when he got his mother to throw in the towel at SSeries 94, costing Bret the belt vs Backlund. That was icing on the cake. His feud with Bret was just so well done. he drew heat just by being in the ring. Even during his nugget run he was spectacular. I loved his whiny heel gimmick.

2: Bret Hart: His anti-USA promos even made me hate him, and I am Canadian.. but I was like 13 when this gimmick happened. His ability to draw heat in the US was just incredible. Even attacking The Patriot during the Star Spangled Banner, genius.

1: HBK: As one half of the rockers, he was super over with the crowd. As his problems with Janetty worsened, his gimmick built. The Barbershop indcident was icing on the cake. His "Better than you" attitude drew great heat. He was also very believable, and I think his heel status made him perform better, and made less talented wrestlers like Crush look good in the ring. although he used a pathetic Teardrop Suplex during most of his heel run, he was fantastic.
 
5 - Ric Flair
nobody can deny what the Nature Boy did for the art of playing the bad guy, i'm not a big fan of him, but i will allways recognize that he's one of the finest heels in Wrestling history...
4 - HHH
i hate this douchebag, but looking back to the late years of the Attitude era, he was The bad Guy, the fans wanted his head on a silver platter, he and Steiner took the sadistic heel to a whole new level in 2000...
3 - Scott Steiner
altough not a douchebag like Helmsley (in real life), Scott was an example of what a heel should be, he was sadistic, didn't give a fuck who stepped on his way, he would turn his face into a banana creampie, also the douchebag promos about his Freaks and his Peaks were a great way to make fans hate him...
2 - Raven
the early days of ECW, the birth of one of the darkest characters in the history of Wrestling, yeah, at first sight he was a thypical 90s Metalhead, but he was an evil mastermind who could brainwash a lot of people, even the Sandman's son... awesome heel, also great as face when the time feels right
1 - Undertaker
not a big Taker's fan, but i'll make an exception about 98-99, yeah, the Lord Of Darkness, the best character Taker ever had, that was the definition of Sinister Heel, i remember being 9 years old and seeing him for the first time and being awe in shock, the human sacrifices, the Austin's crucifixion (something Raven did first), his theme (maybe one of the best themes in Wrestling history), his entrance, his promos, everything on him screamed "Best Heel Ever"...

Honorable Mentions:
Kurt Angle, Hollywood Hogan, Sid Vicious, Scott Hall, The Franchise, Macho Man, Eric Bischoff, Stone Cold, Lex Luger, Dudley Boyz, The Rock, Sting, Mike Awesome (RIP), Kevin Nash, Masa Chono, New Jack, Lance Storm, Roddy Pipper, Test (RIP), Diamond Dallas Page...

Promising Heels:
Mr. Anderson, Beer Money Inc, AJ Styles, Ricky Banderas, Chris Harris, Desmond Wolfe, Abyss, CM Punk, Monty Brown...
 
5. Edge - The Rated R Superstar is a good modern heel. I'd say an even better heel than Orton because he can make people hate him, where as a heel Orton has always gotten cheers.

4. Triple H - He was a great heel back when he was with Stephanie and the whole McMahon/Helmsley Era, but also after the brand split he was a good heel and helped carry Raw through that time. They should do something to turn him heel when he comes back.

3. Hollywood Hulk Hogan - Even thought I liked the nWo, Hulk was a great heel at the time and completely different than the "eat your vitamins say your prayers" guy.

2. The Undertaker (1998-1999) - Like said above the Ministry of Darkness Undertaker was the ultimate heel imo.

1. Ric Flair - Dirtiest player in the game. I've never been a huge Flair fan, I know I know haha but I think he is much better as a heel.
 
So wait a sec, this is "favorite" heels, not "best" heels, right? There are several heels I feel are the best, but a different set who were my "favorites."

To be a favorite heel, I had to both hate and respect them at the time, and I had to WANT them to turn face or give me a reason to root for them.

1. Chris Jericho, circa WCW

The only thing more obnoxious than Chris Jericho in WCW around the late 90's? Me, thinking that Jericho was the greatest professional wrestler in history. I was loud, I was annoying. I mean, I still am, but you get the picture. I was such a Jericho mark and people couldn't stand it. My favorite heel of all time.

2. Ludvig Borga

I liked the guy because I actually agreed with him. He made valid points about issues in American such as crime, pollution, etc. Obviously the US isn't the cesspool he made it out to be, but he still derived a load of heat from fairly accurate observations. Plus, he was a beast of a man, a Finnish powerlifter who had a 700-lb deadlift to his credit.

3. The Brood

Even as heels, I was all over this angle. They looked bad-ass, their music was epic, and they worked some solid matches. Who knew that the 2 guys whom Gangrel "led" in the faction would end up with around 10 World Titles between them only 10 years later?

4. Brock Lesnar

There's something about heels who are legit dominant with an honest to God background in being beasts. I followed Lesnar's career in college, as I was a collegiate wrestler as well, and when he touched down in WWE I flipped out. I watched him dismantle (through some really good matches) guys like Rob van Dam, and then saw him feud with The Undertaker and The Big Show. Such an effective guy.

5. Kurt Angle

See above. I followed Angle as a wrestler through the Olympics, and was a huge fan of his during his heel days. I'll take a legit athlete like Angle or Lesnar over the flashiest babyface any day of the week. For my money, few were better than Angle, and the only times I would root against him were when he faced Jericho. When Angle feuded with Lesnar, I was torn down the middle, and held on to every moment of every match.
 
I have so many favorites I had to make this list out of 10.

10. Raven- I had to pick Raven considering the man abducted the Sandman's wife and child and crucified the Sandman to a cross only to have to apologize afterward.

9. Brian Pillman- The man had the ability to become the biggest face and in only moments got the biggest heel heat of anyone in the ECW arena. The fans went crazy for him until he told the fans he was going to urinate all over the bingo parlor.

8. Curt Henning "Mr. Perfect"- Curt was the all star athlete that was perfect in every way. He was the original narcissistic athlete before Kurt Angle and Jack Swagger.This was a man you loved to see beat just so you could say Mr. Perfect was a loser.

7. Jesse "The Body" Ventura- Jesse was the loud mouth that would call out anyone whether it was in the ring or in the announcing booth with Gorilla Monsoon or Vince McMahon.

6. Rowdy Roddy Piper- Piper was the antagonist long before WrestleMania even took off the ground. The man was able to generate the most heat out of anyone at the time facing Hulk Hogan and later Mr. T in the first two WrestleManias. One of the most famous scenes in WWE history was when Piper cracked a coconut over Jimmy Snuka's head. Not to mention that Hot Rod is probably only one a few wrestlers that have actually been stabbed by a fan at ringside before. If that isn't heat I don't know what is.

5.Ric Flair and the 4 Horseman- I had to mention Ric and the Horseman because they were both heels. Flair was the number 1 heel in the 80's for NWA and soon to be WCW. The 4 Horseman were hated so badly that when they locked Dusty Rhodes in the cage, tons of fans were leaving their seats to climb the cage after them. Every night they had to escape the arena for their lives they were so hated.

4. Mick Foley- This man is the only man I have seen that would actually cut a face and a heel promo at the same time on himself while fans cheer and boo him. Foley may be the underdog and the one fans love to cheer for, but he can easily change the pace and turn into a full fledged heel in seconds. He went from the hardcore legend in ECW to the two faced sellout that loved Eric Bischoff.

3. Bobby "The Brain" Heenan- This man was the reason I tuned in every week to watch Prime Time Wrestling or Superstars in the 80's, early 90's. The man was one of a kind that had incredible heat no matter where we went. Truly the greatest manager of all time along with one of the greatest heels.

2. Jake "The Snake" Roberts- Jake wasn't spectacular in the ring, but he made up for it in mind games. He could cut a promo that would chill you to the bone. Roberts was more like a psychopath or serial killer then a wrestler. That is why he was so dangerous and so believable.

1. Million Dollar Man Ted Dibiase- This man would humiliate wrestlers and audience members week in and week out with his money. People would do anything for money has he laughed in their faces. He was truly the anti hero. I have seen countless wrestlers and television shows come and go that try to follow in the Million Dollar Man's footsteps. They have all failed miserably. The difference between the other heels and Ted, is that is was never a face when he was a competitor. He had the character that could never be a face.

Honorable mentions go to : Shawn Michaels, Hollywood Hogan and the NWO, Randy Savage, Triple H, Kurt Angle, and Paul Heyman.
 
5. Mr. Perfect- When I was younger, I wanted to be just like him. I wanted to be perfect.

4. Ted Dibase- It was good times seeing this man kick the ball from the kid when he was only one bounce away from collecting 500 bucks.

3. Hollywood Hogan- I never liked him as a wrestler but every single week, you wanted to see him get his ass kicked.

2. Kane- Kane was awesome when he first debuted and when he set the casket on fire at the Rumble. That was classic.

And #1 is Mr. McMahon. I say he is my favorite heel because he owned the company, he could whatever he wanted and he didn't want Stone Cold to wear the championship. Almost every single week, you wanted to see what new ways Austin would do to torment McMahon.
 
Stan Hansen-Absolutely hated this guy when i was a kid. The mean son of a bitch, his only motive seemed to be to inflict pain and try to mame his opponent. From the bullrope to the tobacco dripping out his mouth and sometimes spit on his opponent, this man was feared.
Vader-As a kid i was amazed by the viciousness Vader showed. He legitimately scared me. Everything about Vader worked as a heel. From the mask he used to wear to the ring, to his promos where he screamed and spit and just looked like a monster. Not to mention his in ring work was brutal looking.
HBK-In the beginning stages of the Rockers split, you could see so many small heelish mannerisms start to show up in HBK's character. Of course then he was just Shawn Michaels. But, after throwing Jannety through the babershop window, Sherri managing him, and the cocky better than you type promos, including the announcement that he had left the building, the Heartbreak Kid was born as well as one of the greatest heel characters of all time. I never thought the day would come where it would be almost impossible for HBK to be anything but a face.
Jake Roberts-Jake the Snake was an amazing heel. The bible quotes sprinkled throughout his dark menacing promos, along with the snake slithering over his opponents lifeless body after he delivered the ddt fit his character perfectly. One of the best heels ever in my opinion. When he was a face it was hard for me to believe it as a little kid. Oh, crashing Macho Man and Elizabeths wedding and the cobra biting Savage were classic heel moments.
Ric Flair-Before he was a legend, and cheered for his heel acts, Flair was hated back in the day. With the Horsemen protecting his title, and his cockiness, he was the ultimate heel. The promos made you feel like he actually looked down on the fans as not being as good as he, the wrestlers as well. Flair was head and shoulders above the rest when it came to making you hate him. Making you want him to get beat finally. Total package when it came to heel work.

I would also like to mention Orton as the Legend Killer was awesome, so is his current incarnation. Though now he's not a heel, when he was psycho punting everyone, that was awesome. Love Orton as a heel. And, I must mention CM Punk as well. In time I think Punk will be mentioned as one of the top heels ever. His promos are pure gold and in my opinion, he's the best heel in the business today.
 

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