Vincent Kennedy McMahon is the most powerful man in the world of sports entertainment. Like his son Shane, Vince grew up in the business. Vince always wanted to be a wrestler, but his father forbade him from competing. Instead of wrestling, Vince McMahon began commentating for his father's show.

Unlike his father, Vince wanted to take control of the entire country. After working in the WWWF for a few years, he eventually purchased the company from his father. McMahon then purchased the rest of the territories in the mid 80s.

By the late 1980s, Vince McMahon built an empire. The WWE became the most profitable company in the history of sports entertainment. While Mr. McMahon is enjoying the fruits of his labor, making it to the top wasn't that easy. Vince failed many times along the way. In fact, he embarrassed himself quite a few times over the years. However, his failures did not stop him from expanding the WWE. Like an experienced general, Vince always picked himself back up and continued marching forward. Even today, many of us disagree with the current direction of the WWE product, but I have a feeling that Vince has something up his sleeve.

Whether you'd like to admit it or not, Vince McMahon is a genius. The WWE has provided jobs for hundreds of people over the years. Furthermore, the product is enjoyed my millions of fans each and every week. Vincent Kennedy McMahon is a successful billionaire who deserves an applause. With that being said, the rest of this article will be used to ridicule Vincent K. McMahon.

Far too many kind words have been shared about the Chairman of the Board. It is now time to dive into the list of the Top 15 Times Vince McMahon Embarrassed Himself.

15 15. When He Almost Said The He Loved... Roosters

The reuniting of D-Generation X (Shawn Michaels & Triple H) in 2006 was long awaited. While the DX of the 2000s wasn't quite as edgy as the original version, HBK, HHH, and Mr. McMahon were involved in a few classic segments together. Shawn Michaels and Triple H did everything that they could to anger and embarrass Vince. Triple H famously goated Vince McMahon into saying, "I Love Cocks" on an episode of Monday Night Raw. Of course, Vince was referring to the animal, but Triple H and the audience took it a different way.

14 14. When He Took a Lie Detector Test

In the mid 2000s, Vince McMahon and Hulk Hogan worked with each other in a number of segments. At the time, Hogan was wrestling under the name of the masked man known as Mr. America. While it was quite obvious that it was Hogan underneath the mask, Vince decided to make Mr. America take a lie detector test.

When Mr. America was asked if he was really Hulk Hogan, Mr. America replied no. Amazingly, the lie detector determined that he was telling the truth. McMahon was furious, and he then decided to take the lie detector himself.

Vince wanted to prove that anyone could pass a lie detector test. After a few standard questions from the operators of the lie detector, Mr. America took the interview over. Vince was asked if he was the biggest a$$hole on the planet, and he said no. The lie detector determined that McMahon was in fact lying.

Mr. America then asked Vince if he was a pervert. Of course, Vince said no, but he was once again lying. After a few more questions, it was revealed that Mr. McMahon had been pleasuring himself to Torrie Wilson's Playboy spread.

13 13. When He Said The N-Word

There's no greater form of racism than saying the N-Word. Hulk Hogan was recently released for saying the word in a leaked sex-tape. However, back in the mid 2000s, Vince McMahon actually said the N-Word live on WWE television. It might sound unbelievable to some, but it actually happened. Mr. McMahon was speaking to John Cena when he used the highly offensive word. For those of you who are relatively new to wrestling, John Cena used to be a "gangster" who rap battled his opponents. Nonetheless, Vince dropped the N-bomb, and then he walked right passed a bewildered Booker T.

12 12. The Time Stacy Keibler Made Him Lose It

Vince McMahon was looking for a new assistant in the early 2000s. He interviewed several candidates, but none of them were good enough for Vincent K. McMahon. However, he knew he found the right girl for the job when Stacy Keibler walked into the ring.

Vince was sitting at his desk with a huge grin on his face. Stacy jumped up onto the table and began dancing for him. Mr. McMahon nearly climaxed right then and there. He fell over in his chair, and he could barely contain himself. Of course, he eventually gave Keibler the job.

While it's not that embarrassing to lose bodily control in the presence of Stacy Keibler, McMahon is a now a grandfather. Not to mention he was married at the time of this promo. Don't get me wrong, I understand that Mr. McMahon was trying to entertain the WWE fans, but what will his grandchildren say when they see this?

11 11. When He Fought God

In the words of good old J.R, "Vince McMahon is an arrogant S.O.B." Not many people know this, but Vince McMahon actually fought against God in a match at Backlash in 2006. Vince and Shane McMahon were feuding with Shawn Michaels at the time, and Vince actually thought it would be a good idea to book himself and his son against HBK and God. Of course, when it came time for God to enter the ring, nothing happened.

The whole God angle was just idiotic. Thankfully, McMahon has promised that God will never be featured in another WWE storyline.

10 10. The Time He Died

The WWE was a completely different product in the early 2000s. The matches were much more brutal, and the storylines were much darker. Some would say that wrestling was better back then, and I happen to agree. With that being said, there were a few times that Vince took things a bit too far. The time that Vince McMahon's limo blew up with him in it seems to be stuck in my mind for some reason.

Not only was the whole "Vince Death" angle completely moronic, but the timing couldn't have been worse. In the midst of the storyline, Chris Benoit had actually just killed his family and himself. McMahon was forced to break kayfabe and drop the whole angle altogether.

9 9. When He Made Fun of Jim Ross

If there's one commentator that the WWE fans love, it's good old Jim Ross. However, Mr. McMahon has made fun of J.R. too many times to remember. Let's face it, Jim Ross isn't the best looking guy in the world, but that doesn't give anyone the right to make fun of him.

During an episode of Monday Night Raw in the mid 2000s, Vince McMahon put on a Jim Ross style hat and proceeded to mock him. Vince even altered his face to match Jim Ross's. To add further insult, Vince recited the classic J.R. words, "Stone Cold, Stone Cold, Stone Cold."

At the time of this segment, Jim Ross was out of work due to a medical emergency. Of course, Vince decided that Jim Ross's health wasn't off limits. Looking back at it now, Vince really embarrassed himself. However, I doubt that he even feels a grain of regret.

8 8. The Kiss My Ass Club

The Kiss My Ass Club was an absolutely ridiculous creation. Nonetheless, Vince started the club back in 2001. He used it as a way to intimidate the new wrestlers who had joined the company after he purchased WCW. The first member of the Kiss My Ass Club was William Regal, and the last member of the club was Hornswoggle. Other notable members of the club include Shane McMahon, Jim Ross, and Shawn Michaels. I'm still angry to this day that HBK had to join it.

The rules of the club were simple. All you had to do was kiss Mr. McMahon's exposed ass. Sometimes Vince would wear a thong, and other times he would go commando. The Chairman of the Board should be very embarrassed for exposing his old ass on national television. Unfortunately, I have a feeling that Vince doesn't really care.

7 7. When He Kissed Rikishi's Ass

If getting his own ass kissed by a man doesn't embarrass him, I have a feeling that kissing another man's ass might. On an episode of Smackdown in the early 2000s, the Rock gave Vince McMahon a taste of his own medicine. But, before he administered the punishment, The Rock played with Vince McMahon's emotions.

Vince was originally supposed to kiss The Rock's ass, but The Rock decided his lips weren't good enough for the People's ass. At first, The Rock brought out Jim Ross, then decided he had something better, Trish Stratus. Of course, Vince smiled like a kid who was about to open up a Christmas present. Trish even pulled her pants down and bent over in front of him. However, just as Vince was about to kiss Trish, The Rock stopped him. Rikishi's music hit, and that's when Vince knew he was in serious trouble.

At first, Vince McMahon refused to do the job, but after a Rock Bottom, the job was done. Rikishi jammed his giant derriere in Mr. McMahon's face.

6 6. When He "Wrestled" Bret Hart

In 2010, Bret "The Hitman" Hart returned to the WWE for the first time in over a decade. While we were all extremely excited to see Bret return, he wasn't the same man who had left the company in 1997. Nonetheless, Vince McMahon knew that we wanted to see Bret Hart beat the crap out of him.

After a few memorable promos, Vince McMahon and Bret Hart eventually found themselves on opposite sides of the ring at WrestleMania XXVI. Needless to say, the match was absolutely horrible. Mr. McMahon has no athleticism to begin with, but pairing him with Bret Hart was a terrible idea. This would have been a great match 15 years ago. Instead, it turned out to be an embarrassing night for all those involved, especially Vince McMahon.

5 5. When He Blew Out Both of His Quadriceps

We all know that Vince McMahon is about as nimble as Frankenstein. However, what he lacked in athleticism, he made up for in effort and enthusiasm. Nonetheless, nothing could save him from himself at the Royal Rumble in 2005. Supposedly, Batista and John Cena messed up the scripted finish of the rumble. Vince was pissed, and he stormed the ring. Upon entering the ring, he blew out both of his quadriceps. The Chairman couldn't get up. The moment was hilarious for the fans, but it was painful and embarrassing for Vincent Kennedy McMahon.

4 4. When Bret Hart Spit On Him

We all know what took place in the main event of the 1997 Survivor Series. That was the night that Bret Hart was screwed by Vince McMahon. Most people consider the Montreal Screwjob to be the most infamous moment in wrestling history. While it was a dark day for Bret Hart and his fans, it was also one of the most embarrassing nights of Vince McMahon's life.

After referee Earl Hebner called for the bell, Bret Hart immediately figured out what had happened. He looked at Shawn Michaels, and then he stared at Vince McMahon with rage in his eyes. Hart stood up, and then he spit right in Vince's face. HBK wisely left the ring with Triple H at his side.

While the glob of spit that Vince McMahon received was disgusting enough, his night got even worse shortly thereafter.

3 3. The XFL

Vince McMahon is a business genius, but not even he could create a football league that could compete with the NFL. The XFL proved to be McMahon's biggest financial blunder. He lost millions of dollars thanks to the XFL.

When it debuted, the XFL was actually quite popular. However, after only a few games, the XFL's ratings plummeted. It wasn't long until the entire organization was shut down.

Bob Costas famously brought up the XFL in a famous interview with Mr. McMahon many years ago. Costas and McMahon argued, but it was Vince who got the better of the heated debate. Nonetheless, the XFL was a sore subject for Vince McMahon, and it's still the worst business decision of his life.

2 2. When He Danced At The Slammy Awards

In 1987, Vince McMahon was on top of the world. He was the Emperor of the wrestling business. McMahon had Hulk Hogan and Andre the Giant at his disposal. WrestleMania III was a giant success, and Vince wanted to celebrate in tremendous fashion.

At the annual Slammy Awards, Vince McMahon sang the song, "Stand Back." Hulk Hogan was in the background playing the electric guitar. Vince danced around the stage, and he sang terribly. His moves were awkward and strange, but that didn't stop him. The Chairman danced with confidence. The moment is hard to watch without laughing.

Vince McMahon's musical performance is by far the most embarrassing thing that he's ever willingly done on his own. Shawn Michaels and Triple H have even poked fun at it in recent years.

1 1. When Bret Hart Knocked Him Out

After Bret Hart had finished destroying the TV monitors at ringside following the Montreal Screwjob, he eventually returned to his locker room. Vince McMahon was waiting for Bret backstage. According to Bret Hart, the men had a few words, and then Hart knocked him out with an uppercut. In the documentary, "Wrestling With Shadows," Vince McMahon can be seen stumbling in the hallway after the altercation.

The fallout of the Montreal Screwjob was ugly. D-Generation X poked fun at The Hitman by beating up a midget who was dressed as Bret. A week after Survivor Series, Mr. McMahon delivered the infamous line, "Bret Screwed Bret." While it may be true that Bret Hart screwed himself, the entire situation proved to be an embarrassing mess of affairs for Vince McMahon.