It’s a very good thing that Vince McMahon is a really, really good on-air personality. Whether it’s natural-born talent, just being around the business for his entire life, or a combination of both, the owner of WWE is also one of its most compelling characters. Without the juxtaposition of his evil, corporate, conniving Mr. McMahon character to the politically incorrect, beer-swilling everyman in Stone Cold Steve Austin, pro wrestling as we know it today may not even exist. He’s been involved in some of the most important, intelligent, and celebrated storylines in the history of professional wrestling.

He’s also been directly involved in some of the most mind-numbing, idiotic, nonsensical, sadistic, most insensitive drivel ever produced:

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5. The Higher Power

Jim Ross exclaiming, “Aww, son of a b*tch!” before Vince is even finished completing his sentence just about sums up how everyone feels about this angle, which turned out to be one of the biggest flops of all time. I remember being a wide-eyed 13 year-old, suspending disbelief at some of the most outlandish things they threw my way, and criticizing WWF’s poor booking and lack of commitment with this storyline. Basically, in 1999, The Undertaker formed a stable with a bunch of nobodies, hell-bent on completely taking over the WWF. They pillaged, they literally hung members of Vince McMahon’s Corporation on nooses…they even abducted Vince’s daughter, Stephanie. An already interesting angle gained a new wrinkle when The Undertaker claimed that his motivations were not purely his own; he was working for a “Higher Power”. Who was it gonna be? Who was terrorizing Vince McMahon’s entire company, abducting his only daughter, hanging his employees alive and trying to dismantle the entire Federation down to its very foundation?

Why, Vince McMahon of course! Remember that this was the Attitude Era, headed by swerve-artist Vince Russo himself, where in the minds of the creative team, the only acceptable storyline was the one with as many pointless twists and turns as possible, eventually landing on the one culmination that doesn’t make a damn bit of sense. So obviously, the logical answer to the question “Who’s terrorizing Vince McMahon?” was Vince McMahon. Why did he do it? Apparently all that self-inflicted hell was simply a way for Vince McMahon to destroy Stone Cold Steve Austin. The angle was slowly forgotten about after, as a result, Stone Cold was given 50% ownership of the company as some entirely unwarranted reparations from Vince’s wife, Linda.

Internet smarks still often bring this angle up as a “It could be worse” reminder, pontificating that anyone would have been a better choice than Vince McMahon. There are even those who firmly support Jake “the Snake” Roberts as a more worthy Higher Power. When Jake the Snake is a more logical choice for any storyline post-1994, you know you done f*cked up. Even The Undertaker, the most revered veteran in the business and renowned WWE company man, considers this angle the lowest point of his career in one of his DVDs.

4. Vince McMahon vs. Donald Trump in a Hair vs. Hair Match Ostensibly For Title of Most Self-Absorbed Billionaire of All Time

The Mr. McMahon character is portrayed as crass, money-grubbing, and the type of person who will sacrifice family and reputation for unyielding amounts money and power. The real Vince McMahon, however, is…well, crass, money-grubbing, and the type of person who will sacrifice family and reputation for unyielding amounts of money and power. He provides the perfect yin to Donald Trump’s yang, who by contrast is crass, money-grubbing…y’know what, you get it. They’re both greedy heirs to multi-million dollar fortunes, so whatever made McMahon think that the blue-collar everyman he had spent a lifetime creating stories for would be the least bit entertained by two members of the now-coined One Percent must have been some pretty good sh*t. All I know is we got Bobby Lashley barbarically shaving Vince McMahon’s head in front of tens of thousands of people, so the angle wasn’t a total bust.

The biggest travesty here is that Vince’s hair never quite grew back correctly after this stunt, leaving him to forever look like a third-grader whose mother forced him into combing his hair “like a good boy” for school picture day.

3. McMahon Stages Horrible Atrocity, Recants When Actual Horrible Tragedy Happens

Again, in 2007, there was a planned “Vince McMahon Appreciation Day” on Raw, where wrestlers, referees and other personnel were to basically worship the very hallowed ground Vince McMahon walks on (also known as “every day” in Vince McMahon’s deranged reality). McMahon showed up in a strange, detached, almost dissociative state for some unknown reason, nary saying one word to anyone. At the end of the show, a surreal shot is shown of McMahon wandering aimlessly throughout the halls backstage before Jonathan Coachman shows him where his limo is parked. Unfaltering from his frighteningly blank gaze, he slowly goes outside, peering at crew workers and the sky with childlike wonder, and gets into the limo, which explodes like it was rigged to a metric ton of C4 the second he closes his door.

This baffling scene was supposed to be the end of the Mr. McMahon character on WWE TV. He felt it had run its course, but he wanted to end it in memorable fashion. This would have been a strange stunt to pull by its own merit; the week after this episode of Raw aired everyone from the usual squabbling Internet wrestling fan to goddamned financial pundits were questioning whether or not this was a good move. WWE stock actually went down, presumably because of Wall Street traders thinking that World Wrestling Entertainment just aired the grandoise demise of its owner.

But the real horror started the very next weekend, when Chris Benoit callously murdered his wife and 7 year-old son in cold blood, and then hanged himself from his own gym equipment. McMahon’s “funeral” was supposed to be the main story of that week’s episode of Raw, but it was instead a memorial of Benoit’s career (they didn’t have any details; everyone, including WWE, thought Benoit and his family had been killed by somebody else). It was one of those ultra-rare events where even Vince McMahon thought something was more important than his own family’s weekly exploitation, and his death angle was never followed through on, going the way of the Nexus’ “Greater Purpose” and the identity of the Anonymous Raw General Manager — forever forgotten.

2. Myriad Sexually Explicit Scenes Inexplicably Involving Himself and Unattainably Hot Women

A lot of the WWE Divas over the years have been some of the hottest women in show business. So naturally, Vince McMahon over the years shoehorned himself into contrived storylines about him getting down and dirty with them. They were almost always blatant and self-serving; just taking out his sexual perversions/frustrations trying to turn the WWE into his thinly-veiled live action romance novel, with himself as the tattered white silk-shirted Fabio.

As if making out with, simulating sex backstage with, and shamelessly objectifying his female employees on a weekly basis wasn’t enough, he usually took it to depths even the most salacious freaks wouldn’t even dream of. Here is the public face of a corporation, whose happily married wife is sitting backstage watching the goings-on, beaming with pride for her husband who is proclaiming himself to be a “Genetic Jackhammer” and forcing Trish Stratus to strip naked in the middle of the ring, walk around on all fours and literally bark for forgiveness like a shamed daschund. It’s one of the most humiliating, difficult-to-watch, degrading segments in the history of television.

1. Vince & Shane vs. Shawn Michaels & God

And here we are, at, in my opinion, the most insane storyline Vince McMahon has ever concocted. In 2006, McMahon was feuding with Shawn Michaels, who a few years prior had returned to the company a reformed born-again Christian after spending most of his first run with the company in the ’90s in a drug-induced haze even Amy Winehouse would have had to respect. After his return, he was the “Heartbreak Kid” in name only; gone were his overtly cocky ways, selfishness, and rampant substance abuse. He clashed with the boss and the two had a surprisingly highly regarded matchup at WrestleMania that year, which HBK won. McMahon, instead of chalking it up to Michaels being a trained professional and master of his craft for over twenty years of his life, deduced that obviously God was literally on his side, preventing McMahon’s vile wishes from being fulfilled. So at the next pay-per-view, he booked himself and his son Shane vs. The Holy Lord and His son Shawn in a no holds barred match. Before the match, McMahon forced the referee to check “God” for any sort of weaponry (God was being portrayed by a spotlight, for the record). The whole thing just could not get any stupider.

The McMahons defeated Shawn Michaels and the big man upstairs after a troupe of surly male cheerleaders violently assaulted HBK during the match. I…I stand corrected. In WWE, it can always get stupider.

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