Dustin takes a walk on the heel side and looks at a few of the most shocking heel-turns the WWF/WWE has ever seen.

This Sunday, WWE Summerslam will feature a triple threat match as Big Show, John Cena and WWE Champion CM Punk for Punk’s title. Building up to the match, we’ve been treated to glimpses that Punk may soon be going heel once more, after his sneak attack on the Rock shocked fans at Raw 1000. While heel Punk would be a welcome return, what fans really want to see is beloved WWE cornerstone John Cena take a walk on the heel side. It’s unlikely that this will come to fruition anytime in the near future, so let’s take a look back at some of the most shocking heel turns in the WWE.

Hogan Joins NWO

Hulk Hogan is the wrestler who got every kid to respect authority and eat their vegetables. He essentially served as the first ever pillar of the then-WWF so when he shocked the world by attacking Macho Man Randy Savage and aligning himself with Scott Hall and Kevin Nash at WCW’s Bash at the Beach in 1996, fans were devastated. By the end of the video, the ring is full of trash that has been thrown at Hogan in disgust. The Hulkster had never before gone heel, but as Hollywood Hogan of the NWO, he made one of the best heels the company has ever seen. It’s rumored that only WCW owner Eric Bischoff and Hogan himself knew of the heel turn before it happened, shocking not only the fans but his fellow wrestlers alike. That’s the type of emotion a good heel turn can yield and Hogan played it to perfection.

Stone Cold Steve Austin Pummels JR

This one is hard to watch because when Stone Cold Steve Austin went heel and sided with Vince McMahon, it just felt wrong. Whereas Hulk Hogan played the heel to perfection, Austin took his heel turn a step further, after winning the title by pummeling the Rock with a steel chair; Austin shared a beer with his, up until then nemesis, Vince McMahon. Austin overhauled his entire image, going from anti-establishment badass to almost a childlike demeanor where he just wanted appreciation and attention from McMahon and felt like he didn’t get enough respect from the fans. The worst of this heel turn is featured in the above video; Jim “Good Ol’ JR” Ross has long been considered one of Stone Cold’s best friends, a fact that was mentioned quite often throughout Austin’s career, so when JR asked Austin about why he would do it, why he would turn on the fans and on him, everybody sat anxiously knowing what was coming. That doesn’t lessen the impact of watching Austin systematically destroying his best friend, a brutal yet perfect metaphor for his complete change in persona. After this heel turn ended, Austin enjoyed a little time as a fan favorite again, only to once again rip out the fans hearts by joining the Alliance during the ECW/WCW invasion storyline. Still, no heel turn has ever been as brutal as Austin’s deal with the WWE devil himself.

The Undertaker

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(apologies for just a link but this video is harder to find than a non-offensive Eugene moment)

In 2001, the Undertaker became the American Badass, complete with a Limp Bizkit entrance theme on a Harley; the Deadman began to proclaim that the ring was “his yard” and that if you crossed him, he’d have to “make you famous.” It was as ridiculous as it sounds but because it was the Undertaker, there was a certain believability to it still. Here, we once again witness a fan favorite become a heel by pummeling JR and joining Vince McMahon. I remember actually watching this happen and wondering how long it took to convince JR that the Undertaker should mercilessly call him “hillbilly boy,” knock him out and shove his head in Vince McMahon’s ass, but that’s incidental. The Undertaker is the rare exception that he doesn’t really fit as either a heel or a face, he can toe the line and still, you not only respect him but genuinely cheer for him. His Ministry of Darkness gimmick was just plain awesome, the Paul Bearer era was pretty creepy, his American Badass phase helped me win countless matches in WWF Smackdown 2 when I was younger and his current tendency to show up once a year in time to wrestle in Wrestlemania is the perfect end to his illustrious career.

The one thing all of these heels turns have in common is all of these wrestlers did turn face again, regaining their spot in the hearts of the fans and showing that sometimes, it can be fun to turn the expectation on its’ head.