Abdullah the Butcher & Terry Funk (AJPW December 15, 1977)

In December of 1977, Terry Funk and his brother, Dory Funk Jr., took on the team of Abdullah the Butcher and The Sheik in a bloody tag team battle in Sumo Hall in Tokyo.

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Antonio Inoki & Ric Flair (WCW/NJPW Collision in Korea April 29, 1995)

In an industry where weird occurrences are the norm, perhaps one of the strangest events of all took place in April of 1995, when WCW and NJPW went to North Korea to hold two days of grappling in Pyongyang headlined by Japanese wrestling legend, Antonio Inoki, taking on the dirtiest player in the game, Ric Flair.

Sports Illustration had a pretty decent oral history of the entire thing a while back that you can read here.

“Hardwork” Bobby Walker vs. Rick Fuller (WCW Worldwide January 17, 1998)

Back in the 90s I loved me some WCW B and C Shows mostly because they’d have the most batshit insane matchups of all time. Want to see Macho Man take on Ultimo Dragon? Want to watch former ECW stalwarts wrestle the highest flying luchadors Mexico had to offer? Worldwide, Pro, and Saturday Night were the places to be.

But beyond those weird “Yeah, Booker T wrestled Robbie Brookside on an episode of Saturday Night” matches that happened you’d also get bizarre “enhancement talent” vs. “enhancement talent” bouts that were oddly engaging.

Here we have “Hardwork” Bobby Walker taking on one of WCW enhancement hosses, Rick Fuller. Tony Schiavone and Bobby Heenan have an uncomfortable conversation in which Tony tells Brain that “Hardwork” Bobby Walker isn’t related to “Hardbody” Harrison (another black enhancement guy) and it seemed like he was about 3 seconds away from declaring that Bobby Heenan thinks all black people look alike, but I digress.

Fuller’s the bigger man and had at this point gotten some B and C show victories under his belt so he’s my pick to win. Bobby “The Brai” Heenan says that Fuller should wrestle on Nitro though since that’s where the real international talent is and goes on to compare Rick Fuller to a horse as the match gets underway.

Fuller gets some offense in before “Hardwork” goes to town. He outquicks Fuller and even gets the big man up in a power slam before pinning him: one, two, three for the upset victory.