WWE announcer Jim Ross has always had something of an interesting relationship with his boss, Vince McMahon. Over the course of more than 15 years of employment, JR has been the clear-cut best play-by-play man in wrestling, signed many of WWE’s top stars in his former role as head of talent relations, and been a faithful lieutenant to Mr. McMahon all the while. In response, McMahon has fired Ross twice, removed him from television a couple of more times, and booked him in a wide variety of humiliating situations on national television. The most memorable such moment may have occured in November of 2001 when McMahon, perhaps more emboldened by his storyline vanquishing of WCW than his actual purchase of the organization earlier that year, began booking his employees to literally kiss his ass live on The New The National Network. Following the hilarious sight of snooty Englishman William Regal placing his lips on McMahon’s backside, Vince attempted to force his top nemesis, Stone Cold Steve Austin, join the nascent “Kiss My Ass Club.” Unfortunately, for his troubles, Vince had his ass whipped by Stone Cold’s belt.
After seeing JR respond to this butt-striking incident with the fakest laugh this side of the audience at a Mad About You taping, Vince, Kurt Angle and a beanie-wearing Undertaker (spouting such tough-guy phrases as “Vince, drop your pants” and “Pucker up, bitch”) forced Ross to join the club in place of his BFF Austin. Vince, wearing what appeared to be either a prosthetic ass or a pair of flesh-colored briefs, placed JR’s trademark cowboy hat atop his head as Ross’s lips touched his fictitious rear end. McMahon then danced around the ring to the sounds of Limp Bizkit in celebration of one of the most homoerotic segments in wrestling history.
Sadly for Ross, the butt-related humor at his expense was not over. Join us next time as Ross is nearly replaced by a man with zero experience in the wrestling business, hit in the balls by a 57-year-old woman, then had his colon surgery mocked on TV, all in the span of about two weeks.