WWE Raw: Vince McMahon's 8 Worst RAW Moments
Vince McMahon is a jerk.
There’s just no two ways about it.
In fact, the jerk store ran out of Vince McMahon 20 years ago.
Sure, he’s done some stand-up things in his days, and he's provided us with thousands of hours of wrestling entertainment, but his personality leaves a lot to be desired.
He’s also been in his share of atrociously bad, unfunny wrestling segments. This list seeks to find the eight worst Vince McMahon moments on Raw over the years.
He may be the man in charge of the company, and the one who has has final say over everything that goes on the air, but these incidents only count if he actually appeared in the segment.
As we hit Raw 1000, let’s take a look back at our good pal Vince and celebrate…or frown upon some of his more cringe-inducing moments.
8. Put on Some Weight
In 2005, Randy Orton had been out with an injury for a few months with a shoulder injury.
When he returned, his boss, Vince McMahon, had some choice words for him on air:
"What the hell has happened to you? Suit hanging off of you—you've got a neck like a stack of dimes. Are you on some sort of anorexic diet or something? What's going on?"
Why was Vince saying this a bad idea?
Most people think that steroids and wrestling go hand in hand. Vince has been known to like big wrestlers who turn heads at the airport. Randy Orton had lost weight in real life, and Vince made fun of his appearance on TV.
Unless a wrestler wants to be embarrassed by their boss on national television, maybe they'll think they might take some illegal substances to avoid that.
Another reason this was a poor choice of words is that Vince McMahon was also put on trial at one point by the federal government and nearly went to prison.
As the real life owner, there was no reason to point out the legitimate (barely noticeable) weight loss of one of his performers just for the sake of his own ego.
7. Rosie O'Donnell vs. Donald Trump
Rosie O'Donnell and Donald Trump exchanged some choice words in the media. For some reason, Vince McMahon thought a fake match between them would be quality television.
It was not.
Vince McMahon got things off to a mean-spirited start, as he made fun of Rosie O'Donnell and her "lesbianic fury" and called her the "double-chinned diva."
Along with a fake O'Donnell, a Donald Trump impersonator came out and hammed it up for the audience.
The entire segment lasted nearly 10 minutes. The crowd hated it. Vince most likely loved it.
At one point, the crowd even chanted "TNA," marking it as one of the few times that has happened on WWE television.
Vince didn't wrestle in the match, but he did introduce it and probably thought of it, making it one of Raw's worst Vince McMahon moments.
6. Ross' Rectal Exam
Seven minutes. Seven long minutes.
For seven minutes, over 420 seconds, we watched a segment where Vince McMahon pulled objects out of Jim Ross' ass.
Everyone knows that Vince McMahon has a...strange sense of humor. Not many people know that better than Jim Ross.
Ross has long been the butt (no pun intended) of Vince's jokes on-air, but this one went too far and went on for far too long.
Everyone in entertainment knows the rule of three for comedy. Vince McMahon does not.
Instead of pulling three things out of the prosthetic Jim Ross butt and calling it a sketch, he pulled out a football, a goldfish, an owl, an Oklahoma Sooners helmet, some Steve Austin merchandise, a replica of Ross' own head and more.
For this lengthy sketch, what match did this set up? Nothing.
It didn't lead to anything. It was just seven minutes' worth of really bad comedy making fun of a man who is employed by Vince.
The worst thing is, Jim Ross had colon surgery in real life the prior week. Imagine recovering from surgery at your home, turning on the television and watching your boss pretend to pull various objects out of your butt while you're trying to get better.
I can't imagine it either, but it must be unpleasant.
Working for Vince must sometimes be a real pain in the ass (pun intended).
5. Vince Is Full of Crap
D-Generation X had just finished a "hilarious" impression of Vince and Shane McMahon, when the real ones decided they'd had enough.
The two didn't come out alone, though, as they brought backup—the imposing figures known as the Spirit Squad (try to look past the fact that DX beat up the entire Spirit Squad by themselves on multiple occasions).
As the McMahons readied their pipes to give DX a beatdown, Vince stopped and asked why there was a Porta Potty standing on the stage.
Hunter and Michaels then somehow dropped a bunch of um...crap onto their boss, his son and his cheerleader henchmen.
It's a good thing that Vince, Shane and the Spirit Squad decided to stand in the exact spot that all that stuff fell, otherwise the crap would have missed and DX would have just looked silly.
And most importantly, Vince wouldn't have gotten to watch it again later that night and have a good chuckle.
4. Vince Is My Father
Hornswoggle. You either hate him, you're seven years old or you're Vince McMahon.
WWE had a big angle of who was the illegitimate son of Mr. McMahon. Every week, they dropped some clues about who it was going to be, and fans came up with their own line of suspects.
In fact, it was Mr. Kennedy who was supposed to be named Vince's son, but he was suspended by WWE for 30 days due to a wellness violation.
While it was horrible timing by Kennedy, WWE decided instead of waiting 30 days, they wanted to reveal the storyline now, and teach Kennedy a lesson.
But why did Vince also have to take it out on the audience? What did we do to deserve this?
The big moment came, and Hornswoggle came out from under the ring. Vince looked upset, and HHH literally laughed like it was the funniest thing he'd ever seen in his life.
In the end, there was no good reason to play off weeks of TV time to have the payoff be a joke.
And a really, really bad one at that.
3. Vince Mocks JR
Vince and Hornswoggle were chatting it up backstage. This was one time father and son were having a good time, sharing in their mockery of JR.
Vince thought he'd give little Horny some tips on how to do a good JR impression.
He really shouldn't have.
Vince mocked JR's Bells Palsy by mimicking the paralyzed side of JR's mouth while he talked. He did this on national TV in front of millions of people.
Worse yet, WWE was in the midst of their Be A Star anti-bullying campaign as this was going on.
In real life, Vince is the one who keeps arguably the greatest announcer of all time sitting at home while he goes on the air and makes fun of his medical problems.
Why does he do this? Only Vince or a really good psychiatrist could answer that.
2. Bark Like a Dog!
Trish Stratus in her underwear? Cool, sounds great!
Trish Stratus having to strip down to her underwear because Vince McMahon is on a weird power trip and is yelling at her moments after he had her bark like a dog?
I'm...I'm uncomfortable. I need an adult!
WWE is quite often accused of being sexist, and this would probably be exhibit A for that argument.
Who knows why Vince McMahon OK'd this segment? Yeah, it made his character look like a jerk, but this angle made his entire company look horrible in the process.
There's a million ways to get heel heat, but Vince went with a chauvinistic approach that sexually humiliated one of the top females in the company.
It was cruel and hard to watch.
I'd like to think that he learned his lesson from this and no longer wants to embarrass women for his own amusement, but after seeing Piggy James and farting Natalya, I'm assuming he hasn't.
1. Exploitation of Brian Pillman's Widow
"Have you had any opportunity to think of what you, now as a single parent, will do do support your five children?"
Vince McMahon, Brian Pillman's former employer, asked Pillman's widow this question on TV just one day after his death.
Financially, Vince easily could have helped her out. Her husband died while working in his company, after all. Yet he asked her this in front of millions of people in one of the worst times of her life.
He also asked her about medication pain killers, and the speculation that Brian Pillman took too many. Never mind the fact that many wrestlers take pain killers because of the grueling WWE schedule, and the lack of time off that Vince McMahon himself decides upon.
Vince has been in a lot of bad stories, and said a lot of mean things on RAW, but this one was the worst.
The death of Brian Pillman was real. The interview with his widow was also real.
This was a poor lack of judgment from the so called "genius" of wrestling.