Wrestlers are in the business of entertainment and pretty much have to do anything that’s asked of them, or else it’s "pack your bags" time. You don’t want to fall out of favor with your boss in any business, but in professional wrestling, a business that is cutthroat, you are especially at risk if you don’t comply with the boss’s orders. Anyone who has ever worked with Vince McMahon can corroborate this.
The thought of snogging Vince McMahon must have been enough to make any wrestler want to run a mile. Then, there was the infamous "Kiss My A** Club" where Vince made certain wrestlers get down on their knees and kiss his behind. Now that's what I'd call intimate.
Now what does intimacy mean? Intimacy means closeness, either on a physical or emotional level. But there would be plenty of wrestling stars who’d agree that they got way too close to Vince -- too close for comfort.
Whether it was through the "Kiss My A**" club, or on-screen affairs, there have been many wrestlers who have gotten intimate with their gung-ho, power-wielding boss. These are 15 instances where Vince McMahon's employer-employee relations developed on a more intimate level.
13 Candice Michelle
This was one of the more publicized affairs featuring Vince. Having openly admitted to cheating on his wife Linda – lucky her – Vince had no misgivings about flaunting his latest girl on -screen in front of the wrestling public.
Vince must have had Candice Michelle in his sights from the get go; the company selected Michelle straight from the Diva Search after her audition. She began life with the company as a makeup artist, but this gimmick didn’t last long because she was quickly propelled into a prominent role as one of 'Vince’s Devils' and then became the WWE Women’s Champion. There’s no doubting her talent and ability, but perhaps she got to that stage because of Vince.
In 2006, Michelle played the role of Vince’s side action, during which there were a lot of hot and steamy moments between the two, including intense and sometimes disturbing intimate scenes.
12 Bret Hart
The “Montreal Screwjob” is arguably the most infamous match in WWE, perhaps even the most infamous match in wrestling history. It will be remembered for Vince McMahon essentially screwing Bret Hart out of a title; it was a fix and disaster of epic proportions.
Everything had been arranged beforehand, but not in the way Hart thought. Vince ordered the referee to ring the bell when Hart was in a sharpshooter, even though he didn’t submit. To say that Hart was furious would be an understatement. Before trashing the set, Hart ended the night by getting up close to Vince – within spitting distance you might say, and ended up hocking a loogie right on his face. While this appeared on screen during the 1997 Survivor Series, behind the scenes the two men would get even more personal. Bret Hart clocked McMahon, and left a visual record of his frustration right under the eye of the WWE Chairman.
This time, it was Vince who got buried up inside a rump. This time he got up close and personal to another man mountain’s backside– Rikishi’s.
Now Trish Stratus features on this list because she got very intimate with Vince when he was trying to anger his wife, Linda. There was plenty of on-screen kissing and Vince didn’t want people to forget it. In 2001 on an episode of SmackDown, he demanded that Trish get down and become the next member of the ‘Kiss My A**’ club. But as Vince squatted and dropped his pants, Trish escaped and in came The Rock. He had Vince keep his pants down, and had his fun humiliating him a bit, but the real humiliation was to come later in the year from The Rock.
The Rock ordered Vince to his knees, and tried to make him kiss the "People's A**". Vince got very close but it didn’t happen. J.R. then came out and tried to make Vince do the same, but The Rock had something else in mind. Out walked Rikishi, a smile plastered across his face. The Rock subsequently forced Vince’s face right into Rikishi’s finisher the Stink Face for a good ten seconds, marking the end of the club.
The whole Vince-Hornswoggle relationship was one serious storyline, but one that many people may have deemed to be utterly ridiculous. It began in 2007 when it was revealed that Hornswoggle was Vince’s illegitimate son, and culminated with Hornswoggle becoming the 6th and final member of the infamous "Kiss My A** Club."
During this time, Vince was being extremely harsh to Hornswoggle, putting him in the ring against much larger opponents such as the Big Show, apparently in an effort to behave like a model father and show some tough love. Vince demanded Hornswoggle to kiss his butt to show loyalty to his family. He did some butt tricks, bared his cheeks for all to see and squatted down in front of Hornswoggle. A commotion then ensued with Finlay – who was revealed to be Hornswoggle’s actual father – interrupting the butt-kissing ceremony, during which Hornswoggle bit Vince’s rear end. It may not have been the gentle kiss Vince was after, but Hornswoggle’s lips still touched Vince’s derriere, thus making him a member of Vince’s club.
11. The Big Show
This is intimacy on another level, and one that Vince probably still has nightmares about. WWE Unforgiven 2006 was the event where Vince got his comeuppance after subjecting many self-respecting wrestlers to kiss his backside; this time it was Vince who got up close and personal with The Big Show’s – really up close and personal.
It occurred during match four at the Unforgiven event – a Hell in a Cell match, which have always been known for their brutality. This handicap match between DX, The McMahons and The Big Show was no exception – there was plenty of violence, plenty of blood, but for Vince, plenty of Big Show’s crack.
Vince actually tried to get HBK to become a member of his ‘Kiss My A**’ club that night, but the tables turned pretty quick. Shane McMahon was out of it, spitting up blood, so Vince was left on his own. Triple H and Shawn Michaels grabbed Vince and shoved his head right into Big Show’s exposed butt. Vince sniffed 500 pounds of crack that day, something he’ll never be able to live down.
10. Linda McMahon
Although it may be hard to believe – because of all the affairs in front of the cameras (and even off camera) – Vince and Linda McMahon have been married since 1966, and everyone at the company is aware of this fact. Linda has decided to stay away from the wrestling limelight, focusing on her political career instead of engaging with Vince and his on-screen antics in recent years. Perhaps that’s wise, as any wife seeing her husband talk openly about dating and sleeping with other women has to have seriously thick skin. But she realizes that a lot of what goes on at the company is purely for the cameras – like actors having to kiss on-screen – so she lets it be.
Although Linda’s involved with WWE in a more creative capacity, she’s also been involved in a number of on-screen roles, most of which have been with her hubby. These were interesting because the viewers were well aware that they’re a couple. The sedation storyline for example was just bizarre. Vince got up close to a sedated Linda, abused her and then cheated with another woman, all in front of her face.
9 Stacy Keibler
Vince loves new talent and over the years, he’s always been at the center of a story line or other that involves making out with a fresh face in front of the cameras.
Vince contracted Stacy to WWE and put her on the roster for his SmackDown brand. Her initial interaction with the McMahon family was with Vince’s son, Shane, who escorted her into the ring to distract Rhyno. But then Vince took a shine to her and wanted to get involved himself. Stacy danced for Vince in the ring in front of the cameras, which resulted in Vince hiring Stacy as his personal assistant. Things soon got very close and personal. The two got together for a number of make-out sessions – of course in front of the cameras and she was yet another woman that Vince got to fondle and kiss on-screen. It's good to be the boss!
8 William Regal
Current General Manager of NXT, William Regal, is today doing pretty well for himself, that’s despite having to recollect the mentally scarring moment of kissing Vince’s backside back in 2001. Regal was initiated into the club during a segment of Raw. Regal and the audience at the time had no clue what was going on as it was the first time Vince had dropped his pants.
For Regal, it was a case of kiss Vince’s rump or get another job because Regal had previously been a member of The Alliance. Vince knew Regal didn’t really have any other choice except to do as he was told and took delight in taunting and humiliating Regal before the actual kiss took place. Vince did butt tricks, flexed his cheeks and even made Regal apply a coating of lip balm before Regal went in for the kiss and became the first member of the "Kiss My A** Club."
7 Mick Foley
Mick Foley’s on this list because he was trying to be a gentleman, trying to help a girl out, but I’m not sure he would have stuck up for Melina had he known what was coming -- what saving her job would entail.
On an episode of Raw in 2006, Foley joined the "Kiss My A** Club," becoming the fifth member to join by planting a long kiss on Vince’s behind.
Being gross is in itself its own form of intimacy, certainly for Vince anyway who took an enormous amount of pleasure from being kissed on his back side.
Foley obliged in order to save Melina’s job, but it proved to be a fruitless task. After all that, Melina was less than grateful and a short time after the incident, turned on Foley and betrayed him. Foley succeeded in saving Melina’s butt, by kissing Vince’s, but got his own butt fired in the process.
Sable quit WWE in 1999 after taking the company to court with allegations about unfair treatment and sexual harassment. The lawsuit was for $110 million. Vince has always hated people trying to get money from his company, and so with a load of legal muscle behind him, he counter-sued and the matter was eventually settled out of court. After all of this, it was therefore puzzling when Sable returned to WWE in 2003 – not just as another face on the roster, but as Vince’s mistress. During this time, she kissed Vince several times in the ring, once with Vince’s wife, Linda and daughter Stephanie looking on.
Needless to say, the Sable-Vince romance caused a few rifts within the McMahon family on-screen, not that Mr. McMahon seemed to care. Sable had several brawls with Stephanie and even had a scuffle with Linda. Of course the Mr. McMahon character doesn't give a damn how others around him feel, right?
5 Trish Stratus
Trish is arguably the hottest, most famous, successful and most beloved diva to have stepped foot into the ring. She began life with the company as a villainous character but quickly rose through the ranks to become a seven-time winner of the title everybody craves – the WWE Women’s Championship.
But on the road to becoming champion, she had to endure some tough times and was involved in a number of different storylines, one in particular was sure to have made her cringe. She was used to escalate the feud that was growing between Vince and his wife, Linda.
Trish and Vince had a relationship, which occurred when Vince asked Linda for a divorce. Needless to say, the other McMahon family members weren’t pleased with Trish. Stephanie brawled with Trish several times, even getting the better of the future Women’s Champion at No Way Out. But eventually, after plenty of make-out sessions and bitter arguments, Vince discarded Stratus just as quickly as he had picked her up, saying that she was a “toy” he was “tired of playing with.” He then proceeded to humiliate Stratus, making her strip and bark like a dog.
But Stratus got some form of retribution – that slap at WrestleMania X-Seven sure must have felt good.
4 Shane McMahon
Getting employees to kiss your backside is one thing Vince, but getting your own son to do the same is, well, abhorrent. There’s a line to father-son intimacy that mustn’t be crossed, but Vince went so far over the line that night – no son should be subjected to anything like that, especially at the hands of his own father.
Many sons love to brown nose to get preferential treatment, but I’m sure this wasn’t the form of brown nosing Shane had in mind.
To be fair to Vince, Shane wasn’t the intended butt-kisser. Vince demanded Shawn Michaels kiss his cheeks, but instead, with Vince already in the squatting position with his back turned, Michaels grabbed Shane, and shoved his face right between his father’s butt cheeks. Vince wiggled and laughed thinking it was Michaels who was making contact with his cheek, but it was Shane who became a new member of the "Kiss My A** Club" that night. He’d never be able to look his father in the eyes again.
3 Torrie Wilson
A man of Vince’s stature is certainly intimidating for a first-timer coming into the company, especially when that person is to immediately have a number of intimate one-on-one encounters with the man. This all happened when Wilson joined the company – during her first night in fact. She’s said: "First day backstage, I was so nervous. Vince is an intimidating man, and I'd just met him, so of course he's even more intimidating. To have to kiss someone that you're physically scared of, that's frightening." Wilson was new to all of this and the fact that there were no rehearsals really freaked her out. She was told to just jump into it and recalls thinking “this is so messed up right now."
What made the situation even more screwed up was the fact that Vince’s wife, Linda, was by her side, cheering her on and advising her how to go about kissing her own husband. Damn, Wilson must have been confused as hell and bricking it!
2 Jim Ross
Jim Ross, affectionately known as JR, is a much-loved figure and prominent personality in the sport, having been around for what seemed like forever and having graced many events as a commentator, referee and occasionally, as a wrestler.
On the night of November 26, 2001, JR wasn’t at the WWE Raw event in an in-ring capacity. He was watching from the sid-lines, watching Vince drop his pants and attempt to get Stone Cold Steve Austin to kiss his rear. But Austin wasn’t going to subjected to that ridicule, so Vince had to take his anger out on somebody else. He spotted JR chuckling at the sidelines and forced him to get down on his knees and become the second member of the "Kiss My A**" club. The Undertaker turned up to help, but the night ended in a humiliating fashion for JR, with Vince squatting in the ring wearing JR’s hat while JR was forced to kiss Vince’s butt in his hometown of Oklahoma City.
1 Shawn Michaels
Michaels and Vince shared a weird relationship, but things got even more weird very quickly when Michaels was forced to kiss Vince’s rump and became third member to join the club during a WWE Raw segment in 2006.
It was Marty Jannetty who was originally in Vince’s plans, but Jannetty downright refused and ended up getting a punch in the face for his troubles. Michaels ran out and tried to save Jannetty from becoming a member of the club, but things didn’t end well for him. Shane McMahon knocked Michaels out with a chair and shoved his face onto his father’s back end.
This disgusting situation remarkably didn’t really affect the Michaels – Vince relationship. They remained incredibly close, right up until the time Michaels decided it was time to call quits on his wrestling career in 2010 – just watch the video of HBK's retirement speech and you’ll realize how much Michaels meant to Vince and the company.