10 Most Ambitious Wrestling Matches Of All Time

5. Charles Robinson Vs. Gorgeous George - WCW Slamboree 1999

Robinson George
WWE Network

This lasted 10 minutes and 39 seconds. A total midcard über-gimmick match performed by a referee and a glamour model went 10 minutes and 39 seconds.

In WCW.

In 1999.

It was ambitious enough for 1999-era WCW to present a vaguely coherent and entertaining show, much less a match requiring the canniest inspiration just to avoid calamity.

Lil’ Naitch popped everybody like a f*ckin’ cork in his Big Naitch cosplay entrance alone. He posed with precisely none of the gravitas and majesty of his hero, committing fully to the role, and he did the strut. He actually did the Flair strut, and he kicked the bottom rope in a fit of temper, and he sold for Gorgeous George, with an hysterically hammy quality, as if she was capable of breaking his arm.

George’s friend, Miss Madness, attempted to remove the steel chair from his humiliated grasp. Lil’ Naitch in response boomed her on the back of the head with a cheap shot before slamming her to the ringside mats in a perfectly despicable tonal shift. George fired black, lighting up his chest with chops, before Robinson dazzled throughout his dumbass version of the Flair flop sequence.

This was so inexplicably magical that it’s a wonder Pat Patterson didn’t produce it.

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 current 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!