The Undertaker's 24 WrestleMania Matches Ranked - From Worst To Best

The Streak...Is Over(rated).

Taker Mania XXX
WWE.com

At Sunday's WrestleMania 33, The Undertaker is set to settle a housing dispute with Roman Reigns. To whom does the "yard" belong? Normally the stuff of the civil court, the two big dogs will instead fight on the grandest stage for their property.

Match quality is difficult to gauge. While 'Taker has forged a legendary career out of making fools of his detractors, murmurs of his physical deterioration abound whenever he exerts himself with the slightest hint of activity. He was said to be hurting badly after his appearance at the Royal Rumble - and it was hardly the danger-laden, minimum fifteen match he is expected to perform in just a few days. WWE would do well to exploit his condition for maximum drama. He is not what he was.

But then, many fans, dismayed at his Big Evil zombie biker schtick, thought the man had outstayed his welcome at the turn of millennium - years before he embarked on the fabled streak-within-a-streak of a guaranteed 'Mania classic.

He cannot be written off, which is ironic; rumours persist that this might be the Last Outlaw's last stand. If this year is actually it, his best matches will take some beating - but even something entirely average would handily eclipse some - nay, many - of his less glowing efforts.

24. Vs. Big Boss Man - WrestleMania XV

Taker Mania XXX
WWE.com

Michael Cole invited unflattering comparison to the great Hell In A Cell matches which preceded it - but his idiocy was far from the most offensive element of a disaster of a contest.

It was an instant failure. Fans had little interest in it, and they weren’t given any reason to turn up the volume. ‘Taker fell clumsily when delivering one of countless clotheslines. Boss Man, not to be outdone, took years off everybody’s life by taking an eternity to drop ‘Taker with a swinging neckbreaker. The notoriously awful coda was almost karmic.

As the match dragged on, ‘Taker momentarily remembered the stipulation and threw Boss Man into the mesh with a few token slams, before Boss Man cuffed him to it. The match was so powerfully awful that it made a believer out of those who denied the concept of fate. The cuffs broke when Boss Man was in the midst of his beatdown spot. Of course they did.

After little else than minutes of terminally dull, borderline polite exchanges of punches and kicks, Undertaker’s Brood henchmen descended from the rafters and hanged the Boss Man in a supernatural scene even too ridiculous by the dismal standards of the time. “Could this be symbolic?” a prepubescent Cole whined on commentary.

It was only symbolic of how terrible the Attitude Era was at its unspeakably bad nadir.

Contributor
Contributor

Michael Sidgwick is an editor, writer and podcaster for WhatCulture Wrestling. With over seven years of experience in wrestling analysis, Michael was published in the influential 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 former AEW World Champions Kenny Omega and MJF, and surefire Undisputed WWE Universal 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!