WWE is, by its very nature, a babyface territory: throughout its history, the company has been focused on building up the best of the good guys and developing the worst of the heels only for those babyfaces to conquer.
Wrestlemania, as the logic goes, is the company's annual "season finale," where its biggest storylines are capped off and, owing to WWE being a babyface territory, this almost always means that a good guy, at least by WWE's definition, will leave the main event victorious.
However, five times (well, four times and one debatable time), WWE has broken with its long-established traditions and brought up the show-closing graphics with a bad guy winning in the show's final contest.
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#5 WrestleMania 2000
For the first fifteen Wrestlemanias, a babyface walked out of the show's main event with the company's top title (and, for the first nine, that babyface was Hulk Hogan). Diesel, Shawn Michaels, The Undertaker, and twice "Stone Cold" Steve Austin rounded out the list of good guys to close Wrestlemania as "The Man."
As the new millennium dawned, though, WWE found itself in the iron grip of the McMahon-Helmsley Era, the unholy union of heiress Stephanie McMahon and her storyline (and future real-life) husband, Triple H; the pair had ousted Vince McMahon as the head of the company, and their reign of terror led to the firings of many superstars and the forced retirement of fan favorite Mick Foley while claiming both the men's and women's world championships.
Royal Rumble winner The Rock had won the right to challenge The Game on the Grandest Stage of Them All but faced opposition from The Big Show who, in a failed attempt at a redux of the 1994 Royal Rumble ending, was alleged to have co-won the match with The Rock. Show had support from another McMahon progeny in Shane McMahon, and the sibling squabble that ensued brought Vince McMahon out of hiding to throw his considerable weight behind The Rock
Just because one more McMahon needed television time, and because Foley had joked about wrestling retirements lasting mere weeks, Linda McMahon forced her way into the family squabble to give Foley his one and only Wrestlemania main event, and an elimination-style Fatal Four Way with a McMahon in every corner closed out Wrestlemania 2000.
The match would, predictably, come down to Helmsley and The People's Champion; just as predictably, just when The Rock looked poised to capture the strap, the WWE Chairman turned on the superstar he'd backed. Mr. McMahon himself walloped Rock with a chair, allowing Triple H to secure the win and uniting the McMahons with no aspirations in American politics as part of the McMahon-Helmsley era.
While The Rock would lay waste to the assembled heels, this was still the first time a villain had emerged victorious from the show's final match, but would not be the last.
#4 WrestleMania X-Seven
The story heading into the championship clash between "Stone Cold" Steve Austin and defending WWF Champion The Rock at Wrestlemania X-Seven was that Austin was crazed by his desire to regain the championship; during a sit-down interview between the two men and Jim Ross, Austin made plain that becoming champ was the only thing that mattered in his life. He would do literally anything within his power, and make a deal with the devil himself, to put that gold around his waist.
That symbolic boast became literal in the match that resulted; after over twenty minutes of blistering action and numerous finishers from both men (and each men using his opponent's signature maneuvers as well), Austin still could not put away his electrifying opponent. Enter longtime Austin rival Vince McMahon, who allied himself with Austin and provided Austin with a chair that the Rattlesnake would use to batter Rock into oblivion.
An extended and anticlimactic series of chair shots later, Austin finally got his three-count over his rival, and the gold that came with it; Austin and McMahon shared a handshake and toasted each other with some Steveweisers to cement Stone Cold's heel turn as Jim Ross reacted like he was watching Mankind fly off the Hell in a Cell all over again.
Notably, Austin has called this the biggest regret in his career, saying he should have seen the money he'd be throwing away and called an audible by stunning McMahon and remaining a babyface; his desire to turn heel, though, meant a second consecutive spring spectacular would have a downer ending (in this case, a downer ending credited with many fans' decision to walk away from the product).
#3 WrestleMania XXVII
At the very height of the Cena era, The Doctor of Thugonomics challenged everyone's future favorite A-lister (and new dad) The Miz for The Miz's WWE Championship. In the "LOLCenaWins" period of WWE's history, the basic assumption was that Cena would be exiting the Georgia Dome the champion yet again, having earned the right to challenge for it by handily winning RAW's Elimination Chamber match in February. In addition to Cena being Cena, Miz was the heel, and heels were supposed to be in danger at the company's biggest show.
Throughout the story between this match's two competitors, though, was the perpetual antagonism of Wrestlemania XXVII's honorary host, The Rock; making his first major Wrestlemania appearance since the re-formed Rock 'N' Sock Connection took on Evolution at Wrestlemania XX, Rock took potshots at both competitors throughout the beginning of 2011, and throughout this show.
During the match, Cena and The Miz brawled out into the ringside area, then into the crowd, reaching a double knockout in the ringside seating area as the referee counted both men out. The Rock would re-enter the picture, declaring that a show like Wrestlemania cannot end on without a definitive finish to its main event, and ordered the match to be restarted; with Miz and Cena back in the ring, Rock would exact revenge on the leader of the Cenation for an attack on the go-home edition of RAW earlier that week.
A Rock Bottom put Cena down long enough for the villainous The Miz to make the cover for three but, like the last time The Rock was present for a heel championship victory in the show closer, The Rock dispatched the A-lister with a People's Elbow, and the broadcast faded to black with The People's Champion posing triumphantly over the victorious WWE Champion.
#2 WrestleMania 31
The winner of the WrestleMania 31 main event was notable for a number of reasons, not just because he was a heel. First, Seth Rollins, by winning this match, became the first man to win both NXT's and WWE's top championships. Second, in doing so, Rollins also became the first man to successfully cash in his (dented and nearly destroyed) Money in the Bank briefcase on wrestling's biggest stage.
Rollins inserted himself into the championship contest between challenger Roman Reigns and The Reigning, Defending, Undisputed WWE World Heavyweight Champion Brock Lesnar at the most opportune time, waiting until the debut of Suplex City and numerous F-5s had weakened the challenger, and a flurry of Superman Punches and Spears had left Lesnar unable to capitalize on hitting one final F5 out of desperation.
While the two advertised competitors in the main event struggled to regain their breath and take the win, Seth Rollins's music sounded through Levi's Stadium as the Iowan sprinted down the long entrance ramp, briefcase in hand. The match was officially ruled a Triple Threat Match, and The Architect set himself on a history-making offensive.
Rollins's win might have been the fourth heel victory to close out WWE's shining star of its pay-per-view schedule, but it was undoubtedly the most unique, and probably the best-received: Rollins received a hero's welcome at the next night's RAW taping for preventing a Reigns victory (but, in true heel form, turned the crowd back against him within moments).
#1 WrestleMania 33 (kind off)
This inclusion is a controversial one, no doubt, but it earns its spot on this list because of how this match was booked and how fans in attendance saw its winner, Roman Reigns.
Reigns is not a good guy.
Reigns is not a bad guy.
Reigns is the guy, regardless of how fans react; many figures inside the company and out have stated that WWE is as pleased as it could be with the mixed reactions their Samoan superstar gets when he enters arenas. The cacophony of arrogant boos and children's cheers sound like cash registers to a company dead set on selling those smarks Network subscriptions (where they hope to see Reigns demolished) and those children t-shirts.
Reigns and The Undertaker were set on a WrestleMania collision course at the 2017 Royal Rumble when Reigns ended The Deadman's claim at a championship opportunity by tossing him over the top rope. Fans nationwide didn't give a moment's hesitation as to whom they would support in this contest: The Undertaker was always the clear favorite.
The finale in Orlando was, ostensibly, a babyface vs babyface contest, but crowd reactions before, during, and after the match painted Roman Reigns as the bad guy. Ask ten different fans how they felt about Roman Reigns emerging victorious from a sloppy No Disqualification contest where The Undertaker's body seemed to give out on him numerous times (and where Big Evil seemed to be calling it a career) and you'll probably get ten different reactions.
Where there was a unified reaction, though, was in the arena 24 hours later where the assembled Wrestlemania Monday crowd hijacked Reigns' promo to let him know exactly who they felt was the heel in Orlando; in his greatest character work to date, Reigns, in turn, let them know exactly how he felt, too.