The WORST Moment From EVERY WWE SummerSlam
27. Billy Gunn Eats “Mrs. Ass” (1999)
Nobody should sling blame at the company for trying to create fresh main event stars in 1999, and it made sense to try that on for size with Billy Gunn. After all, he'd been over for years as part of D-Generation X and the New Age Outlaws duo, so attempting to turn him from over tag star into over singles star wasn't far-fetched.
It didn't work though.
Gunn's King Of The Ring win didn't magically teleport him to the top of cards, and management gave up on him quickly. By August. he was jobbing to The Rock at SummerSlam and having his face shoved into someone's rear for good measure. The whole shindig was played for laughs as the WWF got experimental with Rocky throughout the second half of the year.
Billy bringing a lady to ringside for this 'Kiss My Ass' match proved to be the worst SummerSlam moment by a mile. Naturally, it was Gunn himself who planted his lips on that woman's behind as Rock turned the tables, McMahons laughed behind the scenes, and fans soaked in the fed's latest obsession with people's faces being rammed into butts.
Sadly for Billy, the match sucked, and his main event push was scrapped overnight. He went back to teaming with Road Dogg (admittedly picking right back up where he'd left off), presumably after devouring some breath mints and washing his face.
'Attitude's' love of toilet humour and all it entailed somehow failed to make him a viable addition to the top line mix. Somehow.