Vincent Kennedy McMahon has been the owner of the World Wrestling Entertainment promotion since he took over from his father in 1982. Ever since then, Vince has made the WWE a global entity, leaving the territory era behind him and the rest of the world of sports entertainment. McMahon has been an on-screen personality since 1969. During his first stint on-screen, Vince would mostly just commentate.

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It wasn't until the Attitude Era that Vince really established his character during his feud with Stone Cold Steve Austin. Ever since creating the character of "Mr. McMahon", he has had plenty of questionable moments that the chairman of a billion-dollar company should have done. So let's go back and take a look at some of those pretty awful moments during the career of Vincent Kennedy McMahon.

10 Making Trish Stratus Bark

Vince McMahon and the WWE weren't the best with the treatment of their female talent until a bit more recently with the Women's Revolution. One prime example of that is the build-up to Shane McMahon vs. Vince McMahon at WrestleMania 17. Trish Stratus would be aligned with Vince for the match and even wheel out Linda McMahon in a wheelchair.

Stratus would be berated on an episode of Monday Night Raw and forced to strip down to her underwear and bark like a dog on her hands and knees. Trish publicly stated at the "For The Love Of Wrestling" convention that she was good with the idea because of her getting revenge on McMahon on the Grandest Stage of Them All.

9 Any Moment With A Woman

Vince McMahon with a woman always spelled disaster during the early 2000s. Vince would infamously have segments where he had Stacy Keibler's legs wrapped around his head. She was trying to get a job as his assistant. Vince would kiss her despite being married to his wife Linda at the time.

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Vince would also write segments on Raw where Candice Michelle would dance for him and "tease" him. He'd also have his moments where he would get to kiss Candice as well.

8 Making Fun Of Jim Ross

Vince McMahon would do a segment on Monday Night Raw in 2012 where he did a gross impersonation of a longtime commentator for WWE, Jim Ross. McMahon would put on a cowboy hat and pull a face making fun of Jim Ross' Bell's Palsy condition.

Multiple people would publicly state their distaste for the promo on Twitter. Former WCW announcer Mark Madden said, "McMahon mocking Ross' Bell's Palsy was unforgivable." This would all be happening while McMahon and the WWE would be promoting the Be a STAR anti-bullying campaign.

7 Tearing His Quads

Now Vince McMahon's "cringey" moments don't always have to be the horrible things he has done, some can be completely insane and even somewhat funny. For example at the 2005 Royal Rumble when John Cena and Batista were both thrown out of the ring by accident.

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Vince would come speed-walking down the aisleway and attempt to slide into the ring, in the process, tearing both his quad muscles. Vince then would have to deliver orders to the referees and wrestlers whilst sitting down on the mat and up against the ropes.

6 Wearing A Durag

Vince McMahon would famously get his head shaved at WrestleMania 22 because of the outcome of a match between Bobby Lashley and Umaga. Donald Trump, Lashley, and Stone Cold Steve Austin would hold him down to deliver the famous haircut due to Umaga losing on behalf of McMahon.

To cover the bald head that he was now rocking every week, Vince would famously start wearing a durag. The moment would be so infamous that Matt Cardona would even wear a similar black sweater and durag combo that Vince wore during his time as ECW World Champion.

5 Calling Cena A Racial Slur

One of Vince McMahon's worst moments came during a backstage segment featuring himself and WWE Champion, John Cena. Now due to Cena's older rapping gimmick, Vince came up to Cena speaking in stereotyped speech followed by telling Cena to keep it up followed by the racial slur.

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The camera would pan over to Booker T with his wife Sharmell while saying "Tell me, he didn't just say that." This wouldn't be the last time a similar promo happened featuring the two, but luckily this time Vince wouldn't spit out any racial comment.

4 Bret Screwed Bret

Nearly every wrestling fans has heard of the Montreal Screwjob, but the interview segment afterward is really what made the Vince McMahon character take form. Jim Ross would interview Vince McMahon, trying to ask what happened at Survivor Series.

Vince would detail how he, the referee, and Shawn Michaels did not screw Bret Hart, but instead, Hart did that himself. This all happened after McMahon made it well-known how integral Hart was to the WWE during his tenure.

3 Kiss My A** Club

Vince McMahon would create a club of sorts, comprised of wrestlers who either needed to show their loyalty toward Vince or be punished for angering the boss. There would be many "members" of this group starting with William Regal. This was done so Regal could keep his job in the storyline on an episode of Raw.

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Other members would include the likes of Jim Ross, Shawn Michaels, Hornswoggle, and Mick Foley. Marty Jannetty, Trish Status, and Triple H would be the three lucky ones who escaped attempts by Vince to get them to join.

2 Having A Match With God

In Mr. McMahon's head, he is the most important person in all of history. Vince even seems to think he is more important than God as he and his son Shane McMahon would have a tag match against Shawn Michaels and the holy figure.

"God" would come to the ring as a spotlight. Since the match was a glorified handicap match, according to WWE records, Vince and Shane hold a victory over the worshiped figure.

1 Interviewing Brian Pillman's Wife

The most disgusting moment of Vince McMahon's on-screen career has to come during his interview with Melanie Pillman after the death of Brian Pillman. Vince would ask horrible questions such as how Melanie would now support five children as a single mother.

McMahon would also talk about Pillman's addictions and Melanie's medicated painkillers in their house. This interview would happen just 24 hours after news broke of Pillman's passing.