10 Most Ambitious Wrestling Matches Of All Time

2. Triple H Vs. The Undertaker - WWE Super Show-Down

Shawn Michaels Undertaker Super Show-Down
WWE

Certain expectations surrounded the ‘Last Time Ever’ match between Triple H and the Undertaker at last year’s Super Show-Down pay-per-view—expectations lowered by ‘Taker’s general physical decline. He could only manage sub-three minutes with John Cena at WrestleMania 34, and so surely, this thing wasn’t going 25+ trademark Triple H minutes.

Essentially, if you escaped with your cherished memories intact, you’d probably be reet.

This thing went 27 minutes and 33 seconds, and it felt significantly longer than that because the Undertaker struggled so badly to perform as even a parody of his old self. He didn’t even have it in him to adequately do his part in a back body drop he wasn’t on the receiving end of. He looked as exhausted out there as he does at the prospect of mustering a half-smile for a fan paying extortionate money to meet him.

And what’s sad or morbidly hilarious, depending on your perspective, is that those cheeky prehistoric bastards aimed to pay tribute to their early 2010s classics, as if this was a narrative continuation of them, and not the last scene in Kingpin transposed to the wrestling arena. What were they thinking?

This was either the most woefully ambitious match in recent memory, or the most horrendously narcissistic.

Contributor
Contributor

Michael Sidgwick (Creative Writing BA Hons) is an editor, writer and podcaster for WhatCulture Wrestling. With over a decade of experience in wrestling analysis, Michael was published in the influential UK institution that was Power Slam magazine, and specialises in providing insights into All Elite Wrestling - so much so that he wrote a book about the subject. You can order Becoming All Elite: The Rise Of AEW on Amazon. Possessing a deep knowledge also of WWE, WCW, ECW and New Japan Pro Wrestling, Michael’s work has been publicly praised by AEW World Champions Kenny Omega and MJF, and Undisputed WWE Champion Cody Rhodes. When he isn’t putting your finger on why things are the way they are in the endlessly fascinating world of professional wrestling, Michael wraps his own around a hand grinder to explore the world of specialty coffee. Follow Michael on X (formerly known as Twitter) @MSidgwick for more!