Top 15 Times Vince McMahon COMPLETELY Crossed the Line

When you run a multi–billion dollar company; you're bound to be a bit eccentric. But when you’re the owner of the largest traveling entertainment company this side of Cirque du Soleil, and you're playing a character in your own fantasy land, you're bound to be downright certifiable at times. Since he became a full-time character in late 1997, Vince McMahon has run the gamut of psychotic emotions and has found a way to make fans laugh, cry, and on several occasions cringe in horror of the depths of the boss' depravity.

It's a weird tightrope walk being a wrestling promoter. Over the years, wrestling fans have shown that they like oddball storylines. So it's up to promoters like Vince to keep coming up with out-there stories for his wrestlers to perform for our amusement. This a daunting task, as not every fan is happy with the directions the product goes in and who is pushed to the top. And as loyal a fan base as the WWE Universe is, they're a fickle bunch too.

Keeping the Universe happy solely falls on the shoulders of Vince McMahon. No matter how inclusive the creative process is, the buck starts and stops with him. Why not? It is his money after all, and his company. He built it up after buying it from his father and has turned the whole thing into the industry that it is today. That being said, the guy has produced some very odd, and sometimes creepy ideas. While there are way more than 15 ideas that left us scratching our heads, here are 15 times the boss crossed the line.

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15 Wins the Royal Rumble

via whatculture.com

The tamest item on this list was Vince McMahon winning the 1999 Royal Rumble, at number two, no less. So, a then–60 year old man who owns the entire company booked himself to be the guy who thwarted Stone Cold Steve Austin's attempts to three-peat as Rumble winner. Granted he won by nefarious means but still in the record books, the boss won the whole shebang and, at least for a brief, time was slated to challenge The Rock at WrestleMania. It must have had an interesting effect on the morale in the locker room; no one was good enough to hang with Austin except the middle-aged, non-wrestler.

14 Fakes His Own Death

via wrestlepundit.com

In the soap opera known as professional wrestling, outlandish things happen all of the time. So when Vince McMahon decided to try to take himself off of TV for a while, he did it in classic fashion. Conceptualizing a "Who Shot J.R?" Dallas style conspiracy, the boss would be blown up in his own limousine. But unfortunately, enough dullards think wrestling is real and called the cops. That and the Benoit tragedy forced McMahon to abandon the whole storyline and launch the whole him being Hornswoggle's father angle instead.

13 Vince vs. God

via complex.com

It was only a matter of time before the demonic CEO and Chairman of the WWE would try to take on the Holy Father. He did so when he was taking on the Born Again HBK. Vince would appear in church, alongside his son Shane who himself was backing away from his old man as he was tempting fate, begging to be struck down as only Vince could. McMahon even challenged HBK and the Almighty One to a tag team match at Backlash 2006, the entryway was bathed in a golden light for the Holy Father. But alas, the Bearded Creator did not show his mug on this night or any other. Can you imagine if Vince booked someone to actually play the part? This entry would have shot straight to number one.

12 Vince Says the N–Word

via manslife.com

Several months ago, the legendary Hulk Hogan became embroiled in a scandal where on a sex tape that he is currently trying to have Gawker sued over, he uttered the N-word. In an instant, the very reason many fans became fans was shooed away from the company so not to create a PR mess. Obviously Vince the character is different than Vince the real-life company owner, but he still acted in exceedingly poor taste when in a backstage segment he referred to John Cena as "his n–word." The jaw dropping moment had Booker T and Sharmell nearby and overhearing the boss' remark, but the whole moment should be erased from WWE memory along with many other items on this list.

11 Kiss My Ass Club

via stillrealtous.com

A grown man, father of two, grandfather of six, and ruler of all that is the wrestling industry in North America should probably not show his derrière on national television. And yet, there is an entire club devoted to those who would devote themselves to him–willingly or not. The Kiss my Ass Club reigned supreme for several years and even inspired a web cartoon. What started as a way for William Regal to keep his job (and his facial expressions are only rivaled by Vince's), the club was there to serve the chairman's musings as everyone from Jim Ross (of course) to even Triple H were not safe from the wrath of the Vince's ass.

10 Vince Mocks J.R. 

via bleacherreport.com

Speaking of embarrassing good old Jim Ross in his home state of Oklahoma by forcing the Hall of Famer to join the club, he has also ripped into the man more times than Ross can shill his barbecue sauce (meanwhile the world condemns Ed Ferrarra for Oklahoma). But the worst of the worst would be several hours after Ross had to have emergency surgery, McMahon's warped sense of humor had him portraying Dr. Heiny, complete with a buxom-blond nurse, because why not? Vince would then pull out all kinds of objects out of JR's backside, set to the tune of classic Ross lines. At least he didn't fire him for missing work.

9 (Almost) Fathering Steph's Baby

via bleacherreport.com

While this one never actually happened (thank the very same God he challenged), it still makes this list for almost happening, as had it not been for Stephanie vetoing the storyline, we might all be remembering puking a little in our mouths. While Mrs. Levesque was pregnant with future company owner number one, Vince got a batcrap crazy notion that he'd book himself to be the father of his own future grandchild. Luckily as creative as Stephanie is, she had no interest in turning the already weird McMahon wrestling family into a weird McMahon inbred wrestling family.

8 Booking Al Snow to Eat Pepper

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Whether he's involved in the angle or not, Vince has also booked some crazy ones over the years that didn't involve himself. Maybe he thought he was ribbing the other WWF or PETA but it was strange as heck watching The Big Boss Man devolve into the most disgusting human being imaginable. He kidnapped Al Snow's beloved pet pooch Pepper and then offering to give him back provided he sit down to dinner with the former prison guard. As Al choked down, even complimenting the Boss Man on how good the food was, only then was it revealed the Boss Man had forced Al to cannibalize his own beloved pet. All of this to set up the brutally bad Kennel from Hell Match.

7 Booking Katie Vick

via bleacherreport.com

If eating your own dog wasn't bad enough, at least in some countries dog is a delicacy–necrophilia though, not so much? But Vince thought it would make for compelling television as Kane was in the middle of a career upswing and feuding with Triple H and Evolution. The boss decided it would be interesting if HHH called out the Big Red Machine for his supposed act of "love" with the corpse of his crush Katie Vick. One better is that it was filmed. The Game, turning his voice up to extra raspy. walked into a funeral home, dressed in a Kane mask and proceeded to hump Katie Vick's brains out literally and physically in one of the most disturbing pieces of WWE TV ever filmed.

6 Booking Rosie O'Donnell vs. Trump

via whatculture.com

Just insult us wrestling fans why don't you? That's exactly what the Chairman did when he decided for his own amusement he'd book his good friend, The Donald, against Rosie O'Donnell while those two talking heads were in the midst of their war of words. Only this was just plain stupid. Two buffoons dressed up as the pair and put on an insipid match, perhaps it would have been memorable had he booked a stellar wrestling match between the two impersonators. Instead, Vince put on tripe that insulted every single fans intelligence.

5 Having the Big O Watching Stacy Kiebler

via oldschooljabronies.com

Newsflash, Stacy Kiebler is pretty hot. So hot in fact that her most alluring and endless legs are insured. That being said, when your boss is portraying a lecherous version of himself watching you undulate all over his desk to get a job as his on–camera assistant, you might have crossed the line a bit. At this point in the company's history, the WWE was already a publicly traded company, which meant stock holders had to sit back and cringe as much as some of the fans. Obviously watching Stacy dance is a pleasure for many fans, but when it's borderline sexual harassment on the part of the boss (even in–character), who looked like he was having an orgasm; perhaps Vince should have rethought his hiring process.

4 Interviewing Melanie Pillman

via culturecrossfire.com

One just lost her husband and father of five children, the other was his boss who just lost a genius and gifted performer in the industry. So naturally, less than 24 hours after Brian Pillman's death, Vince McMahon would interview his widow, Melanie. One would assume that Vince was merely trying to make compelling TV while drawing attention away from the company and letting the world know that she might need some financial assistance. But Mr. McMahon has about as little tact as Sheldon Cooper and thought it would be a good idea to point blank ask the poor woman what she would do to raise the kids. Would it have been nice to break kayfabe and let her know he'd take care of it?

3 The Bob Costas Interview

via youtube.com

To be fair, Bob Costas did provoke the guy right away by asking if he thought the XFL would be around for another year and while you can't blame Costas for asking a wrestling promoter if his football games are also fixed, it was a blatant attempt to elicit a negative reaction from The Chairman. Did it ever, as Vince McMahon the man left the room and the evil Chairman smashed through the door. Despite the faltering XFL, Vince had the opportunity to come off and not seem like the media-perceived carny that they believe him to be. But he actually came off more as a petulant child who doesn't like to be interrupted.

2 Montreal Screwjob

via deadspin.com

It's The Godfather as far as wrestling fans are concerned. The great mafia hit that ended the career of Bret Hart and jump started The Attitude Era. But the behind the scenes portion is where Vince crosses the line. No matter the reasons for it, the guy betrayed his number one guy, along with his own word in the process. Make no mistake about it, several wrestlers (re: Mick Foley, The Undertaker) were not happy at all with this turn of events. Obviously Bret has no one to blame for the rest of problems on how he handled what happened, but everything stemmed from November 9th, 1997, and the betrayal of Bret is Vince's cross to bear.

1 Trish Barks Like a Dog 

via onlineworldofwrestling.com

For all of his machinations and insane ideas, this had to Vince at his Machiavellian worst. The man is a husband, father, and grandfather, so why not have the prolific visage of having a very financially-powered man degrade one of the most beautiful women in the world by verbally berating her and having her strip to her skivvies in the center of the ring for his own evil amusement. But if that wasn't bad enough, Vince would have Trish Stratus bark like a dog for the entire world to see. Way to go Vince - very empowering to women everywhere. Almost 20 years later and it's easy to see how moments like this are still affecting how Vince sees the Divas and their supposed revolution.

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