10 Most Infamous Matches In Wrestling History

Shambolic shadenfreude sh*t-shows.

Chamber Of Horrors
WWE.com

There are so, so many dishonourable mentions to consider.

Al Snow and the Big Boss Man's Kennel From Hell match at Unforgiven 1999 was an obvious contender, but it was really more dull than it was shambolic, despite the best efforts of some drugged-up rottweilers. "Donald Trump" versus "Rosie O'Donnell" from the January 8, 2007 RAW wasn't a wrestling match but a publicity stunt. Bret Hart Vs. Vince McMahon, at WrestleMania XXVI, was under serious consideration - but ultimately it was too depressing to reach the near-shadenfreude tone elsewhere.

That's not to say every match contained herein has taken on a so-bad-it's-good quality. Some are so naff that they can't help but become hypnotising car crashes, appealing to the grimly curious side of the human condition - but others, which demand inclusion, remain so painful, so infuriating, that when the referee's hand strikes three the viewer might as well need scraping off the windshield.

Incredibly, several of the men included here have also been awarded ***** matches by the Wrestling Observer - then again, those matches weren't insanely one-sided cage collisions which narrowly avoided severe distress to an entire ethnoreligious group.

10. Hulk Hogan Vs. Kevin Nash - WCW Monday Nitro (January 4, 1999)

Chamber Of Horrors
WWE Network

By early 1999, WCW's status as North American top dog was in critical condition, but contrary to WWE's revisionist history, the competition for ratings supremacy was very much alive - until WCW managed to commit suicide twice in one night.

Tony Schiavone gave away the result of the taped Rock Vs. Mankind match which aired on RAW that night. "That'll put some butts in the seats," he oozed. It was, of course, deeply ironic. Viewers flocked in their droves to witness Foley's moment of triumph. It wasn't quite the watershed moment it has since been portrayed as; those viewers returned in almost the same number to watch the three hour Nitro's main event.

The WCW World title match between Kevin Nash and Hulk Hogan was a catastrophe. It was a major, much-anticipated match between two former allies and massive stars. It was never going to be a classic, but that much was beside the point. It was huge. It was epic.

It didn't happen. After Nash pushed Hogan into the turnbuckle, detonating the crowd, Hogan responded by gently poking Nash in the chest with his finger. Nash flopped to the mat exaggeratedly. The ruse was revealed; the New World Order - the very faction WCW fans were sick at the sight of - had been reformed.

It was meant to generate controversy, and relaunch the storyline, but the angle only underlined to fans that WCW was manipulative and entirely devoid of original thought. Never again did the company win a ratings battle.

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!