25 Lamest WWE SummerSlam Moments Of All Time
8. Kiss My Ass Match - SummerSlam 1999
In terms of business, it seemed like WWE could do no wrong in 1999 -- but even the juggernaut that was running roughshod over WCW met its match when its higher-ups decided to push Billy Gunn as a singles star. Rechristened "Mr. Ass," Gunn was given the win in the 1999 King of the Ring tournament, and after feuding with his former DX partners, he got into a program with The Rock.
The Rock, being The Rock, overshadowed Billy Gunn at every turn, even debuting his "It doesn't matter what your name is!" catchphrase at the King of the Ring's expense. Before long, it was clear Gunn wasn't going to be a star -- but still, the match was set for SummerSlam, and it had an unusual stipulation: the winner would have to kiss the loser's backside.
When SummerSlam rolled around, Gunn decided to change things up -- he brought an obese woman to ringside and announced that, following his victory, she would act as a substitute posterior for The Rock to kiss. During the match, though, Gunn got cocky and brought the woman into the ring. He attempted to take his spoils early, but The Rock prevented the humiliation, shoved Gunn's face into the woman's rear, and finished him off to win the match. That farce was the semi-main event of the show, and the end of Billy Gunn's push.