Until the Last Minute, Streak vs. Career Is Maybe the Best WWE Match of All Time

I am going to start this piece about the WrestleMania 26 match between Shawn Michaels and The Undertaker before I rewatch it, to explain my predisposition against it and the WrestleMania 25 match Joseph and I have already covered. Gonna give you my hot take first, beginning with a doozy! I won’t log in to my Twitter account to dredge up the DMs, but buried in a conversation I had with Joseph some months ago is a pretty wild claim on my part, given my biases and beliefs about the great sport of professional wrestling, that, if I was watching the matches Michaels was having against The Undertaker in 1997-1998 from the perspective of an evil human being who’d just fucked over Bret Hart, Hell in a Cell and the Royal Rumble casket match would make me feel pretty fucking good about my decision.

Forget, for a moment, that Michaels is breaking down physically at that point and was already at a point of mental extreme that makes every “say what you want about Vince McMahon but he’d never allow his locker room to get out of line” take that emerged in 2023 feel like paid-for snark. Also forget, for a moment, that Bret Hart’s 1997 is, up until he’s forced to feud with The Patriot, one of the greatest single years any wrestler has ever had in WWE, including a strong contender for greatest match of all time that happened to be the true launchpad for a wrestler who changed the cultural zeitgeist. The Michaels/Taker matches from that year are extremely good, Hell in a Cell astonishingly so. They’re big, ballsy main events with big-ass swings for memorable image, chaotic setpieces that make good on the violence and spooky nonsense of Undertaker’s character while turning Shawn Michaels into a truly vile, loathsome son of a bitch instead of a guy you just kinda didn’t like because he whined a bunch. 

Their feud is, I think, the peak of both of their careers from a character standpoint, but it feels a little underserved in the story WWE tells about itself and both men. Hell in a Cell is an all-time important WWE match, but the past is a product, and in neatly packaging it for endless resale, WWE has come to the following conclusions: that match is mostly important for Kane’s debut, DX needs to be shown as organizing itself around Triple H, Mankind vs. The Undertaker is the 90s Hell in a Cell match everybody cares about, and the Michaels/Taker matches that stand as the best, maybe even of all time, are the ones from WrestleMania, both of them old and one of them retiring, neither of them capable of the organic-seeming chaos of their 90s encounters but both perhaps a little smarter with the passage of time or lack of drugs or knowledge of Christ or whatever. 

I liked the WrestleMania 25 match more than I thought I would, but it doesn’t have the same fire as its predecessors. I think a lot of that boils down to Shawn Michaels, whose post-hiatus work I’ve seen a lot of recently, the tone of which is pitched towards biblical epic but, this being wrestling and Michaels being a wrestler whose acting chops were “guest spot on a TV show about a beach” good but not “Walker Texas Ranger” good, often feel like megachurch morality plays. My bias against these matches runs pretty deep — I can imagine Terry Taylor hitting play on the YouTube video of this match for his class at the WWE Performance Center and saying “this is how it ought to be,” putting in another hard day of adding nothing to an artform he’s managed to wring a living out of for longer than I’ve been alive, and I kind of fucking hate it. I know that’s unfair — who knows if he does this, for one — but we are deep into an era of in-ring work that riffs off of these matches despite the fact that most of the wrestlers doing the riffing are nowhere close to the auras Michaels and Undertaker had established in 1992, let alone 2010.

Now with all of the purposefully inflammatory stuff out of the way, I am going to actually watch the match. I will see those of you who are paid subscribers to BIG EGG behind the paywall. The rest of you can either sign up or wonder if I just dumped on the legacy of a match on its 15th anniversary for the sake of ragebait.