5 times the heel stood tall in the WrestleMania main event
WWE always has a "good guy" end Wrestlemania the victor...except when they don't.
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.
#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.