Vincent Kennedy McMahon is beyond a shadow of a doubt the most fascinating figure in professional wrestling history. A cunning businessman, a terrible commentator, a genius, a madman, immensely respected and massively loathed, he’s all those things and more. Tales are legendary of how Vince is able to win your trust even when you know you’re in the right and even guys who he screwed over are in awe of his drive and vision. The man took a major risk with his expansion of the WWE into other territories but it paid off as wrestling needed that evolution to survive and grow and damned if he didn’t pull it off.

Yes, Vince can be a real S.O.B. Hell, he openly admits it. The 2006 McMahon DVD is a fantastic watch as it becomes clear even Vince’s own family isn’t sure where the real man ends and his on-screen character begins. Vince loves to keep people on their toes and comes up with some truly insane ideas like honestly trying to push an angle of Stephanie having his baby. Once Stephanie (immediately) refused that angle, he nonchalantly suggested her brother Shane be the father. There are slews of tales about Vince’s weird habits and being out of touch with current audiences. He does have an ego but then again, WWE is packed with egos so it makes sense the man in charge has the biggest one of all. Vince loves to put on a show but he often goes a bit too far. Yet no matter what, you can’t take your eyes off Vince on camera if only to complain about him. That is the key to Vince McMahon, he always keeps you guessing and knows you want to watch. Here are 15 of the wildest moments Vince has ever given us off camera and just marvel that the real guy may be even crazier than all of this.

15 15. Becoming WWE Champion (Video is no longer available)

To be fair, Vince is hardly the first owner in history to make himself champion. And unlike others (Verne Gagne comes readily to mind), he didn’t keep the belt around himself for years on end, but rather gave it up fast. Still, it has to rank as pretty wild that a grudge match between him and Triple H in September of 1999 had Vince bloodied hard, his ass kicked majorly before Steve Austin interfered to attack Hunter and let Vince win the title. Again, he let it go fast and Triple H won it back at Unforgiven but still has to rank high among ego ruses to make yourself champion of your own company.

14 14. Stand Back

At the height of the Hogan era of the 1980s, Vince was going all out pushing WWE in merchandising and a family-friendly image. A great example was the Wrestling Album that had real singing by the wrestlers. That was followed by “Piledriver,” a 1987 album that would provide theme songs. At the Slammy Awards, a special that took cheese to the extreme, Vince did a full-on musical number for his song “Stand Back.”

You have not lived until you have seen a young Vince McMahon dancing about with gorgeous ladies in a suit, clearly thinking he’s John Travolta when the reality is quite different. It’s become a great way of mocking him over the years as Vince just looks absolutely nutty in all this and why it’s on the list.

13 13. Interviewing For a Personal Assistant

In 2002, Vince showed up at Smackdown to announce he was going to be conducting interviews in the ring for a new personal assistant. This would soon lead to some of the most amazing gifs imaginable. First came a young man who was clearly portrayed to be gay and Vince kicked him out without hesitation. Then, an attractive, qualified lady came out and Vince seemed interested.

Then came Stacy Kiebler who proceeded to do a hot dance on the desk, showing off those stunning legs of hers in a performance that literally knocked Vince out of his seat. His facial expressions are utterly priceless, going wild watching to the point of orgasm and would soon have Stacy as assistant and on-screen mistress to give fans even more expressions to mock.

12 12. Fighting Hornswoggle

When the “Vince is Dead” thing had to end due to the Benoit tragedy, he replaced it with the plotline of him having a secret offspring. It was originally going to be Mr. Kennedy but he got suspended so instead they went for Hornswoggle. So we had antics of Hornswoggle trying to get with Vince who naturally hated it and eventually challenged the dwarf to a steel cage match on RAW.

There are some pretty disturbing bouts in wrestling history but watching a 65-year-old man beat up on a midget who was supposed to be his son, including whipping him with a leather belt, ranks higher than most. Finlay tried to interfere but was handcuffed to the ropes as Vince beat Hornswoggle down and let JBL brutalize the poor guy too. It would be revealed Hornswoggle wasn’t really Vince’s son but it still doesn’t excuse how far he went with this.

11 11. The Kiss My Ass Club

Like so many things with McMahon, it started as a joke that got way out of hand. Right after Survivor Series 2001, with WCW crushed, McMahon brought out William Regal and offered the treacherous former Commissioner his job back if he kissed Vince’s ass. Right there in the ring, Vince slid his pants down to expose his rear end and poor Regal had to kiss it. It was wild the first time so of course Vince had to rub it into the ground, doing it time and again over the years with various stars.

To be fair, he would have it backfire like being forced to kiss Rikishi’s ass or the Big Show’s. However, to be the head of a major wrestling company and willingly expose your rear end on air for people to kiss is pushing your heel standing way too far.

10 10. Antics With Trish

Vince has always had a thing for pushing the hot Divas of WWE, championing Sunny and others. He took it to a bizarre new degree in early 2001 when Linda was “incapacitated by a stroke” and Vince took up with Trish Stratus. At the time, Trish was still just hot eye candy, not the great wrestler she’d become and was coming out in skimpy outfits in various segments to make out with Vince right before Linda’s eyes (which really makes you wonder how those two have stayed together for so long).

The low point was Vince making Trish strip to her underwear in the ring and crawl around barking like a dog. It did pay off with Vince getting his ass kicked by Shane and Linda (even Trish) at WrestleMania but still more than slightly off to see McMahon pushing a gorgeous woman to such extremes for heat.

9 9. Dropping the N-Word

For all his faults, Vince can never be accused of being racist. He basically dislikes all people equally. But when you look at the various wild angles WWE has put out over the years, you can see he enjoys catering to stereotypes quite easily. Still, it requires someone truly tone-deaf to racial matters to do what he did at the 2005 Survivor Series.

In a backstage promo, he and John Cena talked about Cena’s match later that night. Cena was cutting a promo on his chances and how good he felt. This led to Vince laughing and pushing Cena on and yelling out “Keep it up, my n---er!” He walked off, passing right by a stunned Booker T and Sharmell who just stared with the same disbelief fans had over Vince actually doing that. Again, not so much bigotry as just Vince misjudging the audience and how he came off, a pretty common thing for a lot of the entries on this list.

8 8. Blowing Out His Knees

The 2005 Royal Rumble was a nice entry in the card’s history with plenty of big stars. It came down to Batista and John Cena, the two fighting it out before going over the top rope together. The refs argued as to who hit the floor first and that brought out Vince who had been squatting in the booth in the back all night. As soon as he slipped into the ring, Vince managed to blow out both knees and tear both his quads, rising and collapsing.

So we had the bizarre sight of a ring full of refs, Cena and Batista and Vince just sitting in the corner, trying to direct all this as if nothing was wrong. The match was restarted with Batista winning but the story was Vince who, incredibly, was back on his feet in just weeks from an injury that would put most regular athletes on the shelf for a year or more. Maybe those stories of the man not being human aren’t far off after all.

7 7. St. Valentine’s Day Massacre

Say what you will about Vince but when it comes to getting his ass kicked, he gives the people their money’s worth. A highlight of his epic feud with Stone Cold, McMahon was pushed to face Austin in a cage match in early 1999 for Austin’s title shot at WrestleMania.

Before the match even began, Vince climbed to the top of the cage, Austin following, slamming Vince’s head in and Vince, in a sight truly amazing, leapt backward for a 15 foot fall right through the announce table. He was put on a stretcher but Austin pointed out the match hadn’t begun so he grabbed the gurney, ran it down the aisle and slammed Vince into the cage. For the next 10 minutes, Austin beat the living hell out of Vince, rendering him bloody and battered and kept going for more. The Big Show made his debut to interfere but it backfired with him tossing Austin into the cage wall so it broke and Austin could escape to win.

Still amazing to see the owner of the biggest wrestling company on the planet putting his body at risk like this and why Vince does have some respect for taking the same punishment any of his workers do.

6 6. Wrestling His Own Daughter

Stephanie has said she’s not sure who was crazier: Vince for coming up with this match in the first place or herself for going along with it. As part of a long plot of Vince with Sable, we had him and Stephanie going at it in an “I Quit” match. A funny bit on the “McMahon” DVD is that this was just days before Stephanie’s real wedding to Triple H and Linda warning Vince “if you leave her with any marks for that ceremony, so help me…”

It was short but still highly ugly with Vince pounding Stephanie in the ribs with an iron bar and choking her so Linda had to stop the match. Truly one of the most disturbing wrestling matches of all time and makes you wonder what goes through Vince’s head to come up with this.

5 5. Dr. Heiney

Vince has been known to carry grudges to a ridiculous extreme. But what he did with Jim Ross in 2005 was pushing it even for him. When Ross stepped down for colon surgery, Vince did a big thing of him being “fired” for cheering Stone Cold Steve Austin stunning the entire McMahon family.

That was poor enough but the next week, Vince did a full-on vignette as “Dr. Heiney” doing an operation on Ross that was basically yanking one item after another out of a“JR’” rear end. It all ended with Vince yanking a JR doll with a hat and proclaiming “that’s the problem, JR, you had your head up your ass!” It just dragged and Ross himself has stated he found it in terrible taste and was hurt but Vince himself seems to have loved it. Even when he’s having “fun,” the man takes it to an insane degree.

4 4. The Blood Mask

Wrestlemania XIX was boasted as “the match 20 years in the making” as Vince was set to take on Hulk Hogan in a no-holds-barred grudge match. Many rolled their eyes at the idea of using Mania to get out issues known mostly to online fans but it turned into a surprisingly decent brawl. The two played off each other well with both doing blade jobs to enhance things and plenty of nasty bumps.

This led to the now famous image of Vince sliding out of the ring to get a pipe and the cameras catching a stunning shot of Vince, his face covered with blood, grinning manically, the very image of Satan himself. Hogan won but that lone shot of Vince is what fans remember best, pushing him more as the evil owner and why he’s so thrilling to watch at times.

3 3. Killing Himself

Maybe it’s bizarre karma that a storyline so poorly thought out would end up biting Vince in the ass. In 2007, after weeks of being shown as 'falling apart emotionally and mentally,' Vince stepped into a limo that promptly exploded. WWE played this dead seriously announcing that the company chairman was dead, complete with video tributes and wrestlers in mourning. Many cited this as being as in poor taste as you can possibly get as it aped the very real emotions following the deaths of Owen Hart and Eddie Guerrero but Vince’s ego pushed it along more and more. Stephanie and Shane were shown crying about it and WWE would regularly have to state it was the “character” of McMahon that died, not the real guy but of course, that didn’t help matters.

In the end, it blew up in Vince’s face as much as the limo did when the Chris Benoit tragedy occurred and Vince realized there was no way in hell he could continue the charade. So he popped back up alive, claiming he faked his death just to get some reaction and the whole angle was basically never mentioned again. A bad idea that just got worse and even without the real-word shades, would be remembered as one of the most terrible things Vince has done.

2 2. Fighting God

A fun highlight of the 2007 Shawn Michaels DVD has a discussion of this with Michaels himself talking with others as to how they assumed Vince was just joking with the idea until it all got started. As part of the feud with Shawn in 2006, Vince and Shane brought up Shawn’s devotion and religious beliefs changing him and so they challenged HBK and God to a tag team match at Backlash.

This led to several promos where Vince just went all out going wild, including a funny bit in a church spitting out holy water like Triple H. The match itself had a lone spotlight illuminating the ring entrance, slowly heading to the ring before Vince told the ref to check “God” for hidden objects and then got on the mic to yell and tell “God” to back down at which point the spotlight retreated. Declaring “God has left the building,” Vince pounded on HBK with aid from the Spirit Squad to win the match. Yes, it had heat but the bad sort, fans hating the ordeal but of course, Vince just shrugs it off as “God has to have a sense of humor.” Maybe but we’ll see who gets the last laugh in the end.

1 1. The Bob Costas Interview

This tops the list because it didn’t happen in a wrestling ring but in what was meant to be a regular interview. In early 2001, McMahon was a guest on Costas’ HBO show “On the Record.” It started calmly at first before Costas began to press Vince on the failure of the XFL and pressing on making fixing games like wrestling matches which Vince seemed insulted by. Costas pressed more on the material of the WWE at the time and catering to fans with lewd content and Vince got more intense. He was snapping, pointing a finger right in Costas’ face and snapping “shut your mouth and let me answer the question.”

It was a stunning display as Vince turned from the real man to Mr. McMahon on camera and Costas holding firm, at one point saying Vince was rich lecturing on class and Vince snapping that “This is the Bob Costas Interruption Program.” On the McMahon DVD, Stephanie recalls watching the broadcast and groaning “please don’t hit Bob Costas” while Triple H laughs “good thing he didn’t or Costas would have killed him.” Bobby Knight was the next guest and Costas pointed out how, for the first time ever, Knight was the most cool-headed guy being interviewed. Whether it was Vince acting up or really pushed to his limit, it’s a showcase for how the real man may be even wilder than his on-screen character and how he always gives you a great show.