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As fans of professional wrestling we’ve been conditioned to believe that, in the end, the good guy always comes out on top. After months of being bested by the dastardly villain in question, one thing that you can all but guarantee when it comes to the showcase of the immortals is that the babyface will win the feud and the fans will rejoice.
Unfortunately for fans of that narrative, sometimes, things don’t always turn out that way. Sometimes the undeserving bad guy manages to sneak in a big-time win on the grandest stage of them all, and as the years go on, it doesn’t get any less surprising.
Of course, most of these ‘heels’ are deserving of their wins, but as fans, we want to be invested enough to the point where we actually want to see them get their comeuppance.
With that being said, here are our 10 greatest heel WrestleMania victories.
#10 The Undertaker - WrestleMania 18
It may come as a surprise to some in the present day, but back in 2002, The Undertaker was a pretty big heel. He was in the midst of his American Badass gimmick which gave him more of a ‘human’ side, and as it turns out, that human side wasn’t very pleasant. Unfortunately for Ric Flair, he learned that lesson the hard way.
The entire build-up of the Taker vs Flair match involved The Deadman torturing Ric and his entire family, to the point where he even beat his son to a bloody pulp. It seemed as if The Nature Boy was in line for a feel-good Mania win, but alas, not even an Arn Anderson spinebuster could prevent Taker from walking away with the win.
#9 The Iron Sheik & Nikolai Volkoff - WrestleMania 1
This one may seem a little bit random, but hey, sometimes that’s what WrestleMania is all about. Of course, there’s no way Vince McMahon could’ve known his back in the 80s when he booked the finish of this match, but it’s still fun to look back and consider what the process of arranging this bout would’ve been.
The Iron Sheik & Nikolai Volkoff, who were managed by Freddie Blassie, were a classic evil foreign tag team. Together they were virtually unstoppable, and they managed to prove that on the grandest stage of them all. Sheik & Volkoff managed to topple the US Express at Madison Square Garden, capturing the Tag Team Championships in the process.
#8 Yokozuna - WrestleMania 9
This one may seem like a bit of a cop-out when you consider what happened immediately after, but we feel as if it should still count. Essentially, the monster Yokozuna managed to stun Bret Hart in the main event of WrestleMania 9 with a huge victory which saw him win the WWF Championship.
The aftermath of the match saw Hulk Hogan come in and steal everyone’s thunder by defeating Yokozuna in a ridiculously quick match, but hey, we’re going to avoid that little anecdote for now. The fact that they initially had the big bad heel win the belt in the main event of the biggest show of the year was, and still is, truly staggering.
#7 Kurt Angle - WrestleMania 21
The Olympic Gold Medallist Kurt Angle has been through many character transformations since beginning his professional wrestling journey, and most of the time he’s found success. However, above all of his other gimmicks, our favourite by far was his ‘wrestling machine’ persona from back in 2005 and 2006.
Angle went around kicking ass and taking names for months, which eventually led to a showdown with Mr WrestleMania Shawn Michaels in Los Angeles. To this day the match they put on is still considered to be one of the best in the history of the event, and the everlasting image of Angle twisting HBK’s ankle until he finally gives in is iconic.
#6 Edge - WrestleMania 22
For a few years prior to WrestleMania 21, Edge was considered to be a rising star in World Wrestling Entertainment. The multi-time tag team champion was finally starting to establish himself as a bonafide star as a singles performer, and all he needed was one star-making performance in order to take him to that next level.
Step right up: Mick Foley. The Hardcore Legend put on a stunning match with Edge in Chicago, as the Rated R Superstar was able to more than hold his own with the creator of the Hardcore Championship. The match ended with Edge spearing him through a flaming table, and from that point on, his rise to superstardom was inevitable.
#5 Owen Hart - WrestleMania 10
It’s not often that you see two brothers squaring off in a WWE ring, and it’s even rarer to see it happen at WrestleMania. So then, you can imagine the excitement of the WWE Universe when they discovered that Owen Hart and Bret Hart would be squaring off in one of the most anticipated blow-offs to a sibling rivalry in the history of the business.
Many thought Bret would come away with the win so that he could carry some momentum into his world title match later in the night, but instead, WWE pulled a fast one by having the heel Owen get one over on his big brother. It was a shocking result back then and in some ways, it still is to this day.
#4 Randy Orton - WrestleMania 24
Randy Orton doesn’t exactly have the best WrestleMania record in the world, but when he does pick up the win on the big stage, it’s almost always an important moment. One such example came back in 2008 when Orton defied the odds by retaining his WWE Championship against Triple H and John Cena in a triple threat match.
Quite literally nobody was expecting The Legend Killer to walk out of the Citrus Bowl with his title, as evidenced by a poll earlier in the night. Orton managed to deliver a sickening punt to the skull of The Game in the dying embers of the match, and thus, his first ever major WrestleMania moment was born.
#3 Seth Rollins - WrestleMania 31
It was called the heist of the century on commentary that night, and three years on, we’re inclined to agree. The venue was Levi’s Stadium and the match was Brock Lesnar vs Roman Reigns, in a contest that nobody initially wanted to see. As the bout went on, though, it became obvious that we were witnessing something special.
Then it happened. Rollins music hit and he sprinted down to the ring with his Money in the Bank briefcase, and all of a sudden, we had a triple threat match on our hands. Before we could even comprehend what was happening, Seth had nailed Roman with the curb stomp before picking up the pinfall that allowed him to walk out of Santa Clara with the WWE World Heavyweight Championship.
#2 Stone Cold Steve Austin - WrestleMania 17
WrestleMania 17 is widely considered to be the greatest Mania of all time, and a big reason for that is the main event. In one corner you had Stone Cold Steve Austin and in the other, you had The Rock, as the two men prepared to square off for the WWF Championship for the second time at the showcase of the immortals.
We always knew it was going to be a grandstand finish, but nobody could’ve predicted quite how stunning it would be. With multiple swings of a chair and a handshake, The Texas Rattlesnake sold his soul to the devil by siding with Vince McMahon in order to guarantee that he came away from the show with the belt.
The heel turn still gets mixed reactions to this day, but at the time, it was revolutionary.
#1) Brock Lesnar - WrestleMania 30
In many ways, it was the night hope died – along with the childhood of millions.
On April 6th, 2014, Brock Lesnar defeated The Undertaker and broke his legendary unbeaten streak at WrestleMania. The thousands in attendance at the Mercedes-Benz Superdome couldn’t quite believe what they’d just witnessed, and in all honesty, neither could any of us watching at home.
We'd become content with the idea that Taker would continue to hold onto his streak year after year, and all of a sudden, it was gone. This part-time monster heel had walked into the WWE and destroyed one of the most prestigious records we’d ever seen. You can debate whether or not it was the right decision for days on end, but there’s no denying that it’s the greatest heel triumph we’ll likely ever see.
