10 All-Time Craziest Wrestling Match Stipulations

3. Kiss My Ass Match

WWE had run "Kiss My Foot" Matches as a way of humiliating hated heels following long and bitter feuds, so it was little surprise that, during the raunchy Attitude Era, things got bumped up to the level -- in this match, the loser would be forced to kiss the winner's rear end, plain and simple. Of course, the contest involved Billy Gunn, who adopted the name Mr. Ass as he branched off as a singles heel. Gunn won the King of the Ring tournament in 1999, and soon afterward, became embroiled in a feud with The Rock -- all in all, not a bad place for someone receiving his first real singles push. At SummerSlam 1999, the two would clash, but the derrière-obsessed Superstar demanded the unique stipulation. Confident of victory, The Rock agreed. When the match came along, though, Gunn revealed that he wouldn't be putting his own ass on the line -- no, The Rock didn't deserve such a privilege. Gunn brought out a substitute rump, belonging to an obese woman. Still, The Rock was unflustered. When Gunn gained the advantage, he got cocky, and called the woman into the ring. This was his undoing. As Gunn tried to maneuver The Rock's face into the woman's buttocks, "The People's Champion" regained control. He shoved Billy Gunn face-first into the ass, then nailed the Rock Bottom for the victory. Fortunately, there was no more ass-kissing after the match.
 
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Scott Fried is a Slammy Award-winning* writer living and working in New York City. He has been following/writing about professional wrestling for many years and is a graduate of Lance Storm's Storm Wrestling Academy. Follow him on Twitter at https://twitter.com/scottfried. *Best Crowd of the Year, 2013