Introduced in 1985, WWE’s King of the Ring tournament features mostly the company’s upper mid-card and below battling in a single-elimination tournament for a much-coveted push in addition to a novelty robe, crown, and scepter. On top of that, many winners end up adopting a goofy “King” gimmick as part of their victory.
And because it’s a tournament, there are often random, unlikely matchups that occur over the course of a given bracket. Since there have been 22 KOTRs to date — including untelevised events — there are loads of random battles. However, none are more random than these 10 KOTR matchups.
10 1987 - SD Jones vs. Sika
The third-ever King of the Ring Tournament was, like all the ones held before 1993, a house show affair. Randy Savage would beat King Kong Bundy in the finals (though he wouldn't become “Macho King” until two years later), but the first round offered a surprising matchup as perennial jobber Special Delivery Jones took on Sika of the Wild Samoans tag team. While that ending sounds like a foregone conclusion, somehow SD Jones got the win, only to lose to Bundy in the quarterfinals.
9 1988 - Randy Savage vs. Red Rooster
Terry Taylor’s unfortunate WWE persona of The Red Rooster is one of those gimmicks that had fans scratching their heads for decades. Was it a joke, or did someone actually think a pro wrestling chicken was a great idea? Either way, Rooster proved shockingly successful in the 1988 KOTR, running through Marty Jannetty and Iron Mike Sharpe to meet 1987 winner Randy Savage in the semifinals. Savage would defeat Rooster only to come up short in the finals against Ted DiBiase.
8 1989 - Akeem vs. Brutus Beefcake
It’s always funny to delve into the career of Brutus Beefcake. One quickly finds out that, despite seemingly being a semi-prominent name, Brother Bruti wasn’t exactly the most important guy ever outside of being Hulk Hogan’s friend. The dude took part in three straight King of the Ring tournaments and lost in the first round every single time.
His final KOTR effort would be in 1989, taking on One Man Gang, who at the time was repackaged into Akeem the African Dream despite being a white man. Akeem would make it to the semis, losing to ultimate winner Tito Santana.
7 1994 - Bam Bam Bigelow vs. Thurman “Sparky” Plugg
By 1994, WWE was well into the New Generation Era, which featured loads of failed occupational gimmick wrestlers, including Bob Holly’s initial WWE persona, race car driver Thurman “Sparky” Plugg. In this first-round match on Monday Night Raw, poor Sparky had to go up against Bam Bam Bigelow, lasting an admirable six-and-a-half minutes before eating a slingshot splash. Bigelow would end up eliminated in the following round by Razor Ramon.
6 1995 - The Roadie vs. Savio Vega
King of the Ring 1995 is one of the most reviled non-Saudi Arabia pay-per-views that WWE ever put on, featuring exactly zero well-received matches and resulting in an infamous push for Mabel. But the true hero of the 1995 tournament was criminally underrated mid-carder Savio Vega, who seemed to be working through an underdog narrative in the tournament that took him all the way to the finals. But before that, he randomly took on The Roadie — as in, Jeff Jarrett’s sidekick and the future Road Dogg — in the semifinals, which is a great indicator of how weird this edition of KOTR truly was.
5 1996 - Vader vs. Jake Roberts
The 1996 King of the Ring is famous for tournament winner Steve Austin’s promo in the aftermath of his victory over Jake “The Snake” Roberts, where the phrase “Austin 3:16” was born. Roberts basically lucked into his spot in the finals due to an odd finish in the semifinals, where he went up against monster heel Vader. The match went less than four minutes before the referee got knocked over by being too close to a DDT, drawing a somewhat nonsensical disqualification for Vader.
4 1998 - The Rock vs. Dan Severn
The finals of the King of the Ring 1998 would feature rivals Ken Shamrock and The Rock putting on quite a show. However, Rocky had a different MMA fighter/pro wrestler to work through first: namely MMA legend and (at the time) NWA World Heavyweight Champion Dan “The Beast” Severn.
Upon thinking about it, the matchup makes sense, but in retrospect, it's odd seeing a KOTR semifinal match between one of the rising stars in WWE and someone whose WWE career is a footnote to everything else he’s accomplished.
3 2000 - Val Venis vs. Eddie Guerrero
The 2000 KOTR finals would come down to Kurt Angle coming out on top over Rikishi, but one of the more surprising efforts of the tournament would be from Val Venis, who was still a few months away from joining Right to Censor. Somehow, Venis made it to the semifinals, losing to Rikishi, but his quarterfinals match had him wrestling Eddie Guerrero. In context, the two had some kind of altercation on SmackDown in the lead-up to this event, but in retrospect, it feels like a totally random matchup.
2 2002 - Brock Lesnar vs. Booker T
Brock Lesnar would end up being the winner of the 2002 KOTR tournament at the King of the Ring PPV, defeating Rob Van Dam in the finals to kick off his mega-push that would take him all the way to the WWE Championship at SummerSlam. His first-round effort, however, happened on the 6/17/2002 episode of Raw, where he defeated Booker T. While that sounds like it would be an unmitigated squash, Brock was only able to F5 Book into oblivion after the nWo interfered with a distraction.
1 2010 - Ezekiel Jackson vs. Alex Riley
By 2010, the King of the Ring had fallen in prominence so hard that there hadn’t had a devoted pay-per-view for it in eight years, so the whole thing played out on one night of Raw in late November. While this edition featured bigger names like Rey Mysterio, Big Show, and eventual winner Sheamus, it also had a first-round match featuring two forgotten WWE stars in final ECW Champion Ezekiel Jackson and The Miz’s sidekick Alex Riley. Jackson would get the win in less than two minutes, but his following quarterfinals match with Drew McIntyre would end in a double countout.