A heel turn is a wonderful thing. When done correctly, it can completely revitalize a wrestler’s character, giving them a new lease of life and allowing them to flourish in a new role that they were simply born to play. However, this is pro wrestling we’re talking about, so, as per usual, this isn’t always exactly how things end up. Whether it’s because the circumstances weren’t right, the turn wasn’t given enough attention or the wrong person was turned, sometimes a heel turn can get over about as well as the idea of sensitivity training from Scott Steiner. However, because we are a balanced and respectful site, we’re not just focusing on the negatives today; we’re here to celebrate the good and ridicule the bad when it comes to wrestling heel turns, although I know which one of those things I’m looking forward to more.

Anyhow, here are 8 Wrestling Heel Turns That Worked and 7 That Failed Miserably.

15 15. An In-Zayn Reunion (Worked)

We’ll start with the most recent one.

Sami Zayn has been one of WWE’s most underutilised talents ever since joining the main roster in early 2016. After a stellar run in NXT, where he captured the NXT Championship and put on numerous classic matches with the likes of Neville, Samoa Joe and Shinsuke Nakamura, Zayn got lost in the shuffle on the main roster, despite a promising feud with long-time rival, Kevin Owens. Zayn got moved from Raw to SmackDown in the 2017 Superstar Shake-Up and his most memorable moment since that time was a lacklustre feud with Mike Kanellis. Well, until Hell in a Cell 2017, that is.

The main event of the show, a Hell in a Cell match pitting Zayn’s arch-nemesis, Owens, against Shane McMahon, looked to be going the way of Shane-O-Mac as it entered its closing stages. McMahon had Owens laid out on the announce table and was positioned on top of the Cell, ready to leap onto his prone foe and, seemingly, win the match. However, just as Shane was about to crush KO, who should run down to ringside and assist the Prizefighter – why, none other than Sami Zayn. Zayn pulled Owens out of the way of Shane, sending the SmackDown commissioner crashing through the announce table himself, which allowed Owens to pick up the win. Zayn explained his actions on the following SmackDown, saying that he didn’t hate Owens, but rather that he was “right all along,” before embracing his former enemy in a truly shocking move. The two men have been real=life best friends for years now, but, in the WWE, they were always presented as bitter enemies, so this turn was truly something unexpected for the WWE Universe. Also, thank God they’re doing something with Sami Zayn now. It’s about damn time.

14 14. Jeff Hardy Goes Bad... For Three Weeks (Failed)

This one is a bit weird.

Jeff Hardy is an extremely likeable guy. Well, that is once you get past the drinking, the drugs and the ruined matches (here’s looking at you, Victory Road 2011). But seriously, Jeff has done very well to clean up his act since the dark days of his past and now finds himself as one of the most popular and beloved wrestlers of all time. His high-flying move-set and repertoire of death-defying stunts have earned Jeff the respect of millions of wrestling fans around the world, which is why you rarely see The Charismatic Enigma portrayed as a villain. That doesn’t mean it hasn’t happened though. Shame it was a bit crap.

Whilst Jeff’s heel run in TNA in 2010 went pretty well, his first attempt at a turn in the WWE, well, that was less effective. In January of 2003, Jeff ditched his good guy persona and started attacking various babyface members of the Raw roster – Rob Van Dam, Booker T, Shawn Michaels and others fell afoul of Hardy’s rampage. What was this leading to, I hear you ask? Maybe a bold new character direction for Jeff? Perhaps a step away from his usual high-risk style to focus more on pure wrestling skill? How about a brand new partnership with- oh, wait, he went back to being a face less than a month later... and this heel persona was never mentioned ever again... and he actually started teaming up with Shawn Michaels, one of the men he had previously attacked. What? WWE clearly saw that Hardy was no heel and turned him back as quickly as possible, but us eagle-eyed fans will never forget this black mark on Jeff’s WWE career and we will forever remember it as one of the most pointless and ill-thought out storylines of all time.

13 13. Triple H Destroys DX (Worked)

A lot of turns on this list featuring somebody joining up with Vince McMahon. The power of capitalism, everyone.

Triple H took over as the leader of influential Attitude Era stable, D-Generation X following the “retirement” of Shawn Michaels in 1998. In his time as leader, Trips recruited new members Billy Gunn, Road Dogg and X-Pac, entered DX into a high-profile feud with Vince McMahon’s Corporation stable and brought in a revolutionary new healthcare and dental plan for all DX members. Ok, maybe I made one of those up, but the point is, he was a pretty good boss. However, The Game would ultimately end up being the one who killed his own creation.

It’s WrestleMania XV and DX member, X-Pac, is battling Corporation member, Shane McMahon, for McMahon’s European championship. Yes, once upon a time Shane McMahon held a championship in the WWE. (And people get mad about Enzo Amore’s title win.) X-Pac and Shane put on a pretty decent match for what it was, but the most remarkable moment of the bout came at the end, when Triple H and DX member, Chyna, ran down to the ring, seemingly to help their buddy, X-Pac, out. After McMahon’s muscle, Test, was taken out at ringside, X-Pac hit his finisher on Shane and looked ready to claim the European title. However, Chyna would put a stop to this when she distracted the referee, allowing Triple H to enter the ring and deliver a Pedigree to his former friend, X-Pac. In a shocking twist, Triple H aligned himself with The Corporation, helping McMahon retain his title and bringing to an end one of the most popular factions of the time in DX. It was unexpected, it was meaningful and it happened at The Grandest Stage of Them All. Doesn’t get much better than this, really. Well, obviously it does, or we wouldn’t have a list, but you know what I mean.

12 12. What Were They Fink-ing? (Didn't)

Jesus, Howard, what the hell was this?

Howard Finkel is a bona fide legend of the wrestling business. The voice of the WWE for much of the 1980s, '90s and early 2000s, Finkel served as ring announcer for most of WWE’s programming during this time and was the first employee ever signed to the company by Vincent K. McMahon. Finkel was also a huge player behind the scenes in WWE as a member of Vince McMahon’s “cabinet”, a trusted group of advisors Vince would turn to in his hours of need. In fact, it was Howard who came up with the name “WrestleMania” when the idea of an annual supercard was pitched by McMahon in the mid-1980s, a name that is now the most famous wrestling event in the world. All-in-all, it seems pretty hard to have anything bad to say about The Fink. That is, however, until you look at his heel run from 2002.

Finkel had been a part of WWE storylines before 2002, but they were always as a loveable character in need of rescue from heel wrestlers. In 2002, however, Fink decided he’d had enough of being nice and decided to become an absolute d*ck instead. He began insulting female members of the Raw roster and going after Raw announcer, Lilian Garcia, whom he was convinced had stolen his spot. The culmination of this “feud” was an evening gown/tuxedo match between Garcia and Finkel, where the winner would be the first person to strip their opponent to just their underwear. I don’t know what’s worse here; the idea of Howard forcibly stripping Lilian, or the idea of Howard in just his underpants. Anyway, Finkel lost and mercifully this was the end of the storyline. Finkel would revert back to being just a plain old announcer and WWE never tried to do a storyline where a neutral figure turned heel ever again. Didn’t they, Michael Cole from 2011?

11 11. The Shield Cracks (Worked)

Good thing I didn’t start writing this list a few weeks ago, otherwise I may have made some comment about The Shield never getting back together. And then I would have looked dumb.

Seth Rollins, Dean Ambrose and Roman Reigns made a huge impact when they first debuted in WWE. At Survivor Series 2012, they ran in from the crowd to prevent Ryback from capturing the WWE Championship from CM Punk, delivering a vicious beatdown and then a trademark Triple Powerbomb through the announce table. Yes, Ryback was once taken that seriously. I’m as surprised as you. This began a nearly two-year-long rampage by The Shield that saw all three men capture championship gold, take on three veterans at WrestleMania and win and main event a WWE Pay-Per-View for the first time when they defeated Evolution at Extreme Rules 2014. However, as the old saying goes, “all good things must come to an end," a saying Seth Rollins must have been a big fan of.

The night after Extreme Rules 2014, Evolution members Triple H and Randy Orton confronted The Shield in the middle of the ring. Batista should have been there, but he was too busy being a famous movie star to participate. After their defeat the night before, fans expected Evolution to be a lot more crest-fallen. However, Triple H had one trick left up his royal sleeve; a trick that revealed itself when The Game uttered the now-infamous words, “there’s always a plan B.” With this, Rollins, steel chair in hand, brutally attacked Roman Reigns from behind, laying the Samoan out as Ambrose watched on in horror. Dean was next to be laid out, leaving the newly-heel Rollins standing tall over his fallen brethren, with his family of Triple H and Randy Orton at his side. Ugh, can you imagine that family at Christmas? This heel turn was effective for two reasons; one, because the Shield were such a popular group, so their breakup had a huge emotional impact on the fans, and two, because so many people had gotten the idea of Dean Ambrose turning heel into their heads, that Rollins being the one to break the group up was a truly shocking twist. Although, if it had been Reigns that had turned heel, we’d have saved ourselves a whole lot of trouble further down the line.

10 10. JR’s “Razor” and “Diesel” (Didn't)

To this day, I still don’t understand what WWE were thinking here.

When Kevin Nash and Scott Hall left for WCW in 1996, it left a particularly bad taste in the mouth of one Vince McMahon. Not only had he lost two of his top talents in Hall and Nash (who performed under the names Razor Ramon and Diesel respectively in the WWE), but they were being used in such an effective way in WCW (more on that later), that they were threatening to put the WWE out of business. Something needed to be done and Vince realised that the only way to solve this problem was to act rationally and maturely. Then he remembered he was Vince McMahon, so he did something stupid instead.

Throughout the summer of 1996, WWE Commentator, Jim Ross (or Good Ol’ JR, as he’s best known), continually referenced the fact that he was “still in touch” with Hall and Nash, even though they had left the WWE. On a September episode of Raw, Ross cut a heel promo addressing this situation, announcing that he had been the one responsible for allowing so many WWE talents to leave for WCW, running down the company for their past treatment of him and outing Vince McMahon as chairman of the WWE for the first time ever (in storyline). Finally, he revealed his big secret; Razor Ramon and Diesel were in the building! Well, actually, they weren’t; they turned out to be two imposters pretending to be the characters. Yes, everybody, Vince McMahon was so petty, he booked two random bozos to dress up like Hall and Nash’s former characters in an attempt to get his own back. Real mature, Vince, real mature.

The angle was gratefully dropped after a few weeks and Ross returned to his previous character, but this was such a stupid and pathetic storyline that it’s still made fun of to this day, even by wrestling fans who weren’t alive when it aired. At least things didn’t work out too badly for Fake Diesel, though, as he would go onto ditch the gimmick and re-debut the following year as The Big Red Machine, Kane. Don’t ask me about Fake Razor, though. I have literally no idea what happened to him.

9 9. Andre Gets “Shirty” With Hogan (Worked)

I really hope “shirty” means the same thing in the US as it does in England. Because that is a genius pun I just made.

Andre The Giant was an absolute megastar back in the day. His incredible size made him a true main event attraction in 1980s WWE, earning him the nickname “The Eighth Wonder of the World.” However, the condition that cause’s Andre’s size (gigantism) also had negative effects on his health and mobility. By 1987, Andre could barely move and he knew his in-ring career was going to come to an end within a few years. So, in an attempt to give Andre the main event push he so desperately deserved, Vince McMahon did something drastic; he turned the big man bad.

On an episode of Piper’s Pit in early 1987, Andre was presented with a trophy for being the “only undefeated wrestler in history.” Of course, this wasn’t true (Andre had lost by countout and DQ a whole bunch of times), but that wouldn’t have made for a good story, so shut up. Andre was quite upset about this, because, some weeks earlier, Hulk Hogan had been presented with an even bigger trophy for being WWE Champion for three years. Feeling underappreciated, Andre and his new manager, Bobby “The Brain” Heenan, confronted Hogan in the Pit. Andre made a challenge for Hogan’s WWE Championship at the upcoming WrestleMania III and cemented his heel turn by grabbing The Hulkster by his shirt and ripping it off. This might sound about as threatening as mouse with asthma, but, at the time, this was huge. Andre had been one of the company’s top babyfaces for so long that him turning to the dark side was something a lot of fans never thought would happen. Couple this was the unstoppable manner in which he was presented on TV and plenty of wrestling fans thought this was truly the end of Hogan’s championship reign. Obviously it wasn’t (Hogan’s backstage politicking was still the strongest force known to man at this point), but the match they had at Mania III is still widely regarded as one of the biggest in the event’s history and this feud helped propel WrestleMania from a success to a global phenomenon. Not bad for a dude who couldn’t walk.

8 8. Big Show Turns On Team Cena (Didn't)

I’m laughing just thinking about this.

Where to begin with the Big Show? There’s a running joke amongst wrestling fans about Big Show’s face and heel turns, because The World’s Largest Athlete has made so many of them during his time with the WWE that they have lost all meaning entirely. According to a list I found on squaredcircle.net, Big Show has turned heel/face a whopping 27 times during his WWE career. 27 times! And this isn’t including the numerous turns he had in WCW either! Seriously, Show, what is going on with you? Is it really that frustrating not being able to buy off the rack clothes?

The one heel turn I’ll focus on for this article is the one from Survivor Series 2014, Show’s last heel turn (for now, at least). After splitting with tag team partner, Mark Henry, Big Show joined Team John Cena to take on Team Authority in a match that would determine the fate of the WWE; if Team Cena won, then the evil authority would be banished from WWE forever, if they lost, then everyone on the team apart from John Cena would be fired. The Authority may have hated Cena, but there’s no way they’re giving up those merch sales. After eliminating Henry (who was on Team Authority) seconds into the match, Show eventually turned on his team, knocking out John Cena before walking away, leaving Dolph Ziggler in a 3-on-1 scenario that he was only saved from by a debuting Sting. By this point in time, Show’s “shocking” heel turn, was nothing more than a joke and almost damaged a really good match. Big Show is a face now, but be careful, everyone, you never know what might set this giant off again. Maybe he just needs a hug, not that I’m volunteering.

7 7. The Corporate Champion (Worked)

The Great One sure knows how to make a Great Heel Turn.

Dwayne Johnson is a man who owes pretty much his entire career to a successful heel turn. When Dwayne first appeared in the WWE, it was as a classic “blue chipper” babyface named Rocky Maivia; happy, full of smiles and generally quite boring. This led to fans turning on The Rock more than Baywatch was panned by the critics (sorry, Dwayne, but come on), booing him, even chanting “Die, Rocky, Die”, because wrestling fans are horrible people. In order to put a stop this, Dwayne took a huge risk and made a drastic change to his character; gone were the smiles and in was a cocky, trash-talking jock character, who joined up with The Nation of Domination. After this, he was simply known as “The Rock”. The rest, as they say is – IT DOESN’T MATTER WHAT I SAY!

Whilst The Rock’s first heel turn was completely revolutionary in terms of his character, I’d have to say his second heel turn in 1998 was far more effective. It took place at Survivor Series of that year in the finals of the Deadly Games tournament to crown a new WWE Champion. The Rock, who had been rising up the ranks as one of the biggest faces in the WWE, was facing off against Mankind, a puppet of Vince McMahon, in the finals of the tournament. The Rock had fought his way through the likes of Big Boss Man, Ken Shamrock and The Undertaker in gruelling matches to earn his way to the final and had the fans behind him all the way. However, as it turns out, their support was entirely misrepresented. In the dying embers of the match, The Rock managed to trap Mankind in a Sharpshooter submission, grabbing the ropes for leverage. Rather than breaking the hold, the referee was rang the bell, before Mankind tapped out. In a reference to the Montreal Screwjob the year before, The Rock was crowned the new WWE Champion and revealed himself to be the newest addition to McMahon’s Corporation. And the fans, oh, they did not like this. A shocking turn that came in the middle of a meteoric rise to the top, Rock’s heel turn in 1998 was expertly done and it lead to a brilliant feud between him and Mankind and later Stone Cold Steve Austin. Can’t argue with that, really, although, I suppose some of you will.

6 6. New Blood, New Goldberg, Bad Idea (Didn't)

Ooh, WCW in 2000. Bad times.

By the year 2000, WCW were losing the Monday Night Wars to the WWE and they were losing it badly. In a desperate attempt to get themselves back on track, WCW put together two of the most controversial figures in wrestling history; Eric Bischoff and Vince Russo. You know when your two drunk uncles get together at a family gathering and start singing really badly? This was basically the wrestling equivalent of that.

At The Great American Bash 2000, Jeff Jarrett was defending the WCW Championship against Kevin Nash in the main event. Jarrett was on the side of Russo and Bischoff, who (of course) made themselves powerful on-screen characters as the leader of a new stable called The New Blood. I don’t know why it was called The New Blood, because Jeff Jarrett (who was just 32 then) looked as old as Mount Rushmore. The end of the match came when long-time WCW favourite, Goldberg, turned heel and speared Kevin Nash, saving Jarrett’s title reign and aligning Goldberg with The New Blood. Sadly, this meant that Goldberg was now a heel... even though everyone loved him. Right. Sometimes this can work and a beloved babyface can become a despised heel. Sadly, WCW were in dire need of top faces, evident in the fact that Goldberg switched back to being a face a few weeks later. A sign of a company on its knees, Goldberg’s heel turn was poorly managed in every way and it’s no surprise that the company was dead within a year and a half. Seriously, if you ever think your life is going poorly, just remember that you never made David Arquette the world champion.

5 5. That Austin/Hitman Double Turn (Worked)

You know which one I mean. You know.

The year was 1997. Bret “The Hitman” Hart had been a WWE employee for over a decade at this point, but his goody two-shoes shtick was getting pretty old with the audience. On the other hand, there was an up-and-coming star rising quickly up the WWE ranks; a Texan by the name of Steve Austin. The two had a great feud in the early part of 1997 over Hart wanting to teach respect to the disrespectful Austin that even involved Stone Cold stealing a win in the 1997 Royal Rumble from Hart. The feud was set to come together at WrestleMania 13 in what promised to be a good match; however, Austin was going into this match the heel, whilst Hart was the face. But, fear thee not, oh loyal readers, for this was about to change.

In a brilliant match, easily the match of the night, Austin and Hart took each other to hell and back in a No-DQ Submission bout. Austin was bloodied, brutalised and beaten by Hart and the Canadian suffered equally at the hands of The Rattlesnake. In one of the most iconic WrestleMania moments of all time, Hart trapped Austin in his signature Sharpshooter hold in the middle of the ring. Austin, with blood dripping down his face, screamed out in agony, but never tapped out, keeping his hands flat upon the blood-soaked canvas, taking the punishment like a real hero. Eventually, Austin passed out from the pain, losing the match, but refusing to tap out to Hart, which only made The Hitman even angrier. In a beautifully executed move, Austin had been turned into a beloved good guy, whilst Hart had transitioned into a full-blown villain, brilliantly setting up the two men’s character trajectories for months, even years to come. Whilst Austin’s face turn was the real story here – seeing how it created the biggest star in wrestling history – let’s not forget how well Hart played his part in this match. Without Hart’s heel turn, there would have been no Austin face turn, and that’s got to count for something.

4 4. “I Did It For The Rock” (Didn't)

Oh, Rikishi.

Cast your minds back: it’s Survivor Series 1999 and the scheduled main event is Triple H defending his WWE Championship against The Rock and “Stone Cold” Steve Austin in a triple threat match. However, Austin had been suffering from neck problems in the lead up the match and it was determined that he was unable to compete. So, to cover this up, WWE ran an angle in which Austin was hit by a car just before the match, removing him from the match within storyline. Whilst this may seem like an ingenious, last-minute cover-up by the WWE, in actual fact, the company had planned for Austin’s absence weeks in advance, but didn’t tell the fans because they were afraid they’d lose out on money. Thanks, guys, thanks a lot.

Almost one year after the event, the mysterious attacker was finally revealed. Fans had been kept on tenterhooks for nearly twelve months over the identity of the assailant and everyone had their own theories about the driver; was it old enemy, The Rock? Was it Triple H trying to stop Austin from taking his title? Was it a brand-new wrestler debuting in grand fashion? Nope. It was Rikishi. The dancing fat man in a thong. Yep. Rikishi claimed he did it “for The Rock”, protesting that Samoan wrestlers like Rock and him were always held back at the expense of white performers (let’s leave that can of worms closed for the time being), turning heel in the process. After almost a year of intrigue, almost a year of mystery, almost a year of suspense, fans were left thoroughly disappointed with this lacklustre reveal, especially when it was revealed that it was Triple H who had hired Rikishi to drive the car. Then why didn’t you just make Triple H the attacker in the first place?! Seriously, WWE, it’s not hard.

3 3.  HBK Shatters The Rockers... And a Window (Worked)

Or, if you ask Bobby Heenan, Marty Jannetty was trying to escape through that window.

The Rockers (known as The Midnight Rockers before joining WWE) were one of the most popular tag teams of late '80s WWE. The athletic, good-looking team of Marty Jannetty and Shawn Michaels wowed audiences with their impressive in-ring ability and, despite never winning the tag team championships, they were still highly respected amongst the WWE audience. Then, one fateful night in 1991, Jannetty and Michaels decided to take an ill-fated trip to The Barbershop.

After tension between the two had been mounting for a few weeks, Shawn and Marty were guests on Brutus “The Barber” Beefcake’s talk show segment, The Barbershop. The segment (which aired in January 1992) seemingly showed the team reconciling their differences and embraced each other, to huge applause from the crowd. However, this would be a very short-lived moment of happiness, as Michaels took this opportunity to introduce his partner to the bottom of his boot. Michaels superkicked Jannetty as the crowd watched on in horror. The future HBK then cemented his heel turn by picking Marty up and throwing him through one of the windows on the set of the segment, breaking the class and breaking up The Rockers once and for all. This was a perfectly executed heel turn, as the audience were taken on an emotional rollercoaster throughout this segment; the tension before the interview, followed by the relief at the apparent reconciliation, then the shock and horror at Michaels’ betrayal of Jannetty. This would be the moment that would catapult Michaels to stardom, allowing him to transition into his famous “Heartbreak Kid” gimmick and slowly rise up through the ranks of the WWE to become one of its most famous and admired stars. As for Marty, well, let’s not get into that now. I want this entry to end on a positive note.

2 2. Stone Cold Sells His Soul (Didn't)

As funny as the guitar-playing and the cowboy hats were, this just wasn’t Stone Cold.

WrestleMania X-Seven is universally recognised as the best WrestleMania of all time. So many legendary matches took place on this show; Triple H vs The Undertaker, TLC II, Kane vs Big Show vs Raven for the Hardcore title. Hell, even the gimmick battle royal was fun and that had The Gobbledygooker in it. However, out all these legendary matches, there’s one that stands out above all the rest – The Rock vs Steve Austin in the main event for the WWE Championship. Whilst some people may have enjoyed the match for its intense action, gripping story and brutal bumps, most people remember this match for one reason and, sadly, it’s not the best one.

Towards the end of the match, Austin hit Rock with a Stunner, but only had him pinned for a two count. Frustrated, Austin knew he needed some serious help and that help presented itself in the form one the man standing at ringside; Vince McMahon. In a shocking move, McMahon handed Austin a steel chair which he used to batter The Rock with. After this brutal assault, Austin pinned Rock to claim his WWE Championship, celebrating with McMahon, the man he once considered his most hated foe. Whilst this was certainly shocking and memorable, that’s all this moment was, because, when you look into it, this turn made no sense. Firstly, Austin didn’t actually need McMahon’s help here – all Vince did was hand him a chair, something Austin could have just walked twenty feet and gotten himself. Secondly, the WWE audience did not want to boo Austin. The company had spent the last two and bit years building him up as their top guy, only to have him go bad on the Grandest Stage of Them All (in Austin’s home state of Texas, no less) and they expected the audience to boo their hero. Of course it didn’t work! Whilst this was certainly a memorable end to a memorable show, in the long run, turning Stone Cold heel just wasn’t the right decision. And that’s the bottom line... because I can’t think of anything else to say. Sorry.

1 1. Enter The nWo (Worked)

Cue the music.

The New World Order (nWo) are one of the most influential stables in the history of pro wrestling. Fuelled by the departure of founding members of the group – Scott Hall and Kevin Nash – from the WWE to WCW, the nWo built itself on reality-based storylines, something that fans (who had grown tired of the silly, cartoonish nature of pro wrestling) were dying to see. The nWo also pioneered the “cool bad guy” trope of pro wrestling that still exists to this day; they were villains and portrayed as such, but they did in a way that made fans want to see more of them. Well, that was until it got massively out of hand and began the focal point of literally every storyline in WCW. That kinda killed the company.

One of the reasons that nWo was so popular was the incredible way in which they debuted. At Bash at the Beach 1996, Hall and Nash were facing off against Sting, Lex Luger and Randy Savage in the main event. The heel duo of Hall and Nash promised that a third man would join their team against the good guys, but this third man wasn’t present at the beginning of the match, so the contest began as a handicap. However, towards the end of the match, who should come to ringside but none other than Hulk Hogan, one of the longest-established and famous babyface icons of all time. See where I’m going with this. In a truly shocking move, Hogan turned heel for the first time in almost twenty years, aligning himself with Hall and Nash and forming the New World Order in the process. This was a truly revolutionary move on WCW’s part – the equivalent of John Cena turning heel today – and helped put them significantly ahead in the Monday Night Wars. Seriously, this heel turn almost put the WWE out of business; it was that good. A shocking twist, a memorable angle and spot on casting, Hulk Hogan’s turn to the dark side in 1996 may just be the greatest heel turn in pro wrestling history. Well, maybe not as good as Hogan’s other heel turn – you know, the one with those leaked tapes...