WWE: 10 Most Inappropriate Stipulation Matches Ever

4. Kiss My Ass Match

Only in wrestling, folks. In 1999, Billy Gunn was in the middle of his greatest singles push to date and had adopted the moniker of "Mr. Ass." Heading into that year's SummerSlam, he was engaged in a fairly heated program with The Rock, whom he had screwed out of a WWE Championship opportunity in July at Fully Loaded. With a major pay-per-view match between them looming, the decision was made by the writing staff to add a stipulation. See, two talented guys such as Rock and Gunn could not have a good, old-fashioned wrestling match near the top of the card. No, they needed some sort of stipulation to really put the match over the top. It was decided that, to play up Gunn's nickname, the match would be a Kiss My Ass match. Yep, the loser of the match would be forced to pucker up and plant their lips on the backside of the winner. How anyone thought either man would be able to retain dignity or be taken seriously after such a humbling act remains a mystery. There was no way Rock was losing, not as the face of the WWE, which meant Gunn would waste all of the momentum that he had built on one moment that would ultimately kill his push. To make matters worse, Gunn had brought a heavier woman to ringside and planned on having Rock kiss her ass. It backfired and Gunn found his face shoved in the woman's ample posterior. http://www.dailymotion.com/video/x17k6h3_summerslam-1999-the-rock-vs-billy-gunn_creation Vince McMahon would institute the "Vince McMahon Kiss My Ass Club" two years later but in that context, it worked. He was an abusive boss who got off on humiliating his employees. He loved to prove to the world who was in charge and he did just that by forcing the men and women that worked for him to pucker up and literally kiss his ass on live television. It helped get William Regal over as an even bigger heel than he already was and became a staple of McMahon's feuds throughout the mid-2000s. Two grown men fighting to avoid having to kiss the other's ass? Not so effective.