3 Backstage WWE incidents that left Vince McMahon in tears, and 3 times he laughed out loud

When one looks back at some of the greatest characters to ever come out of pro-wrestling, the Mr. McMahon gimmick is always brought up. Vince McMahon kept himself away from the weekly action for years and was mostly seen behind the announce desk. It all changed in the mid-90s, and Vince slowly began inserting himself into what was going on in the squared circle. He went on to become one of the biggest heels in the business and had memorable feuds with the likes of Stone Cold, Shawn Michaels, and Triple H.

Over the years, there have been tons of instances where Vince McMahon couldn't control his emotions, while there are some that made him laugh out loud. Let's look at all of these moments in detail.

#3 When Vince McMahon cried: Vince learns about Stone Cold's neck injury

By the time 1999 was about to come to an end, Stone Cold had become hands-down the biggest Superstar in all of WWE. His rivalry with Vince McMahon was the highlight of the era. At Survivor Series 1999, Austin was set to compete in a Triple Threat match for the WWE title, against The Rock and Triple H. On the same night, Austin was run over by a mystery man in a parking lot. This was done to write him off TV as he was about to undergo neck surgery.

In his book, "The Stone Cold Truth", Austin revealed Vince's reaction when he learned how serious the Rattlesnake's injury was.

J.R went into Vince's office and Vince's eyes were red, and he was wiping the tears from his eyes... he really cared.

Austin came back soon after WrestleMania 16. Three years later, his neck issues forced him to retire as an in-ring competitor, following his WrestleMania 19 encounter with The Rock.

#3 When Vince McMahon laughed: R-Truth pitches hilarious idea to Vince

The 2016 Royal Rumble match was won by Triple H. Fans still talk about one particular moment from the match to this day, involving R-Truth. He came out believing that it was a Ladder match, and took out a ladder from under the ring and set it up to a chorus of cheers. Truth was quickly eliminated, but the moment will live on in fans' minds as one of Truth's absolute best. Truth later revealed that Vince McMahon "burst into laughter" when he pitched the idea to him.

He was like, ‘What?’…‘What if I had a ladder underneath the ring for the Rumble?’ and he looked at me and burst out laughing, and said, ‘We’re doing it.’

The Ladder spot is just one of several hilarious moments of R-Truth's WWE career. He took it up a notch last year when the WWE 24/7 title was introduced and the fans got to witness some incredibly creative title changes over the next few weeks.

#2 When Vince McMahon cried: Vince fails to describe what The Undertaker means to him

Undertaker: The Last Ride is an in-depth look at the legendary career of the WWE veteran. The documentary features a long string of backstage clips that we hadn't seen before, plus a bunch of interviews with WWE Superstars as well as Vince McMahon.

In one of the clips, Vince McMahon is asked what The Undertaker means to WWE and him. The boss, who's already an emotional mess, makes the "cut the tape" gesture and says that he "can't do that" while shedding tears.

Vince McMahon later did provide a comment, and had nothing but praise for The Undertaker:

Undertaker, Mark Calaway, is the most loyal performer I’ve ever dealt with, and he is the kind of man that you would want literally and figuratively in the foxhole with you.

The Undertaker has been a part of WWE for three decades. He made his way to WWE in late 1990 and spooked the fans with his sinister persona and presence. It's baffling how The Deadman managed to stay relevant for three decades in a business where most wrestlers get burned out in a matter of years.

#2 When Vince McMahon laughed: Major botch makes Vince laugh hysterically

During her 4-year stint with WWE, Kaitlyn won the WWE Divas title on one occasion. In August 2012, she participated in a Battle Royal, with the winner getting an opportunity to compete for the Divas title. The match was supposed to end with Eve Torres winning, but a Clothesline from Kaitlyn proved too strong for her and she was knocked out of the squared circle. Kaitlyn was worried about Vince McMahon possibly fuming backstage at what had happened, but she was surprised to see him having a blast over it.

I legit thought that when I walked back through the curtain that I was going to be fired. That was right on the cusp of the Divas getting more opportunities, so I was like, ‘Oh my God, I’ve f***** everything up.’ I walked back and Vince McMahon is laughing hysterically. I was like, ‘Is it an evil laugh, or…?!’

The eventual plan didn't change though. Kaitlyn was attacked by Aksana at Night of Champions, leading to Eve Torres beating Layla to win the title.

#1 When Vince McMahon cried: Vince's final meeting with CM Punk

Following his appearance in the 2014 Royal Rumble match, CM Punk quit Vince McMahon's company and hasn't made a return to the squared circle as an active competitor ever since. Months after his WWE exit, Punk appeared on Colt Cabana's podcast and discussed in detail exactly what made him quit.

Punk stated that he met Triple H and Vince McMahon before leaving. The Game didn't show much emotion, but Vince McMahon actually cried at seeing Punk leave. According to Punk, Vince cried while saying goodbye, and told him that he was family. Months later, Vince went on to apologize to Punk for sending his termination papers on the day of his wedding.

Punk made waves last year when it was revealed that he had signed a deal with WWE Backstage. He appeared on the show occasionally as an analyst and special contributor. Recently, FS1 announced that the production of the show had been halted, and one wonders if this was the last we saw of Punk, in regards to pro-wrestling.

#1 When Vince McMahon laughed: Vince's reaction to fan backlash following Hell in a Cell

At Hell In A Cell 2019, the main event was a Hell In A Cell match for the Universal Championship, pitting Seth Rollins with The Fiend. The controversial ending to the bout saw the referee disqualifying Rollins after he attacked The Fiend with a sledgehammer. The Sacramento fans booed Rollins out of the building and chanted "AEW" and "Refund" at the end of the show. As was expected, fans slammed the match on social media as well. WWE Chairman Vince McMahon wasn't worried about the reaction though.

Reportedly, Vince McMahon didn't take the reaction in a negative light and was laughing about it. The feud continued past the PPV, and the two rivals met at WWE Crown Jewel 2019. This time, The Fiend succeeded in defeating Rollins and winning the Universal title. He kept the belt on his shoulder for months on end, before dropping it to WWE Hall of Famer Goldberg at Super ShowDown 2020.