Every WWE King Of The Ring Winner Ranked From Worst To Best

21. Billy Gunn (1999)

Billy Gunn King Of The Ring 1999 Win
WWE.com

When you talk about trying to use King of the Ring as a vehicle to push a wrestler, you have to point to Billy Gunn as a prime example. Unfortunately, he’s a case study that even at the height of WWF’s popularity, even the then-vaunted KOTR wasn’t a sure thing.

Gunn was already a wildly successful tag team wrestler and part of one of the most popular stables during the Attitude Era, D-Generation X. But in 1999, WWF charged ahead with plans to make him the next breakout singles star. Having him win the 1999 King of the Ring tournament was the right play to launch that initiative.

Unfortunately for Mr. Ass, he fell flat on his… well, ass, right out of the gate.

Someone decided it would be a great idea to pit Gunn, who never was known as being strong on the mic outside of one hit catchphrase, against The Rock. One can only guess how that went for Billy, as Rocky wasn’t about to treat him with kid gloves. Rock shredded Gunn on the mic and beat him at SummerSlam, sending Billy back to Road Dogg for a New Age Outlaws reunion by the fall.

Gunn would putter about for a few years until he was released in 2004. He’d return to the company later, but he’s since then found a home in AEW.

Contributor
Contributor

Scott is a former journalist and longtime wrestling fan who was smart enough to abandon WCW during the Monday Night Wars the same time as the Radicalz. He fondly remembers watching WrestleMania III, IV, V and VI and Saturday Night's Main Event, came back to wrestling during the Attitude Era, and has been a consumer of sports entertainment since then. He's written for WhatCulture for more than a decade, establishing the Ups and Downs articles for WWE Raw and WWE PPVs/PLEs and composing pieces on a variety of topics.