10 Harrowing Wrestling Matches That Are Incredibly Difficult To Watch

1. Jim Neidhart & King Kong Bundy Vs. Jake Roberts & Yokozuna - Heroes Of Wrestling 1999

One of the most infamous and infamously awful wrestling events of all-time, Heroes Of Wrestling - a merciful one-off event featuring the faded stars of yesteryear - unintentionally staged one of the grimmest scenes in wrestling history.

Jake Roberts was deep in the throes of alcoholism by 1999, and he relapsed to a depressing extent prior to the show. His pre-match promo has taken on mythical status. “You don't want to play cards with me because I'll cheat. Okay? I cheat. You wanna play 21? I've got 22. You want to play blackjack? I've got two of those, too! You wanna play...Aces and eights, baby? I got too many of those, too!" After he made his agonisingly slow entrance, he suggestively cavorted with his trademark snake, kissing it, positioning it as a proxy for his penis, lewdly stroking it up and down.

Naturally, his match with Jim Neidhart fell apart. The promotor, Bill Stone, frantically combined it with the King Kong Bundy Vs. Yokozuna main event, but Roberts was too out of it to do anything else but withstand depressing punishment. As Bundy and Neidhart attempted a double team spot on Yoko in the ring, Roberts, out of his head, could only stagger around and prop himself up on the apron.

It’s hard, even disturbing, to watch - but, paradoxically, it makes his eventual recovery all the more uplifting.

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!