Vince McMahon vs Kurt Angle vs the Undertaker

Date: May 6, 2001
Location: Atlantic Ocean (in the air)
Source: It’s True, It’s True by Kurt Angle, Armpit reader Justin Newbould

Vince McMahon and the WWF always made a fortune touring Europe, even when their domestic business in the US was weak. In 2001, following the purchase of WCW, business started a downward slide they’ve still yet to recover from. In that era, their bright new star was Olympic gold medalist Kurt Angle.

Angle is considered perhaps the quickest learner the business has ever seen. After six weeks he was ready for the main roster, with 2000 being his breakout year where he became a main event star. Additionally, his legit sports background gave him instant credibility with the media, making him a perfect representative of the company. After Austin’s heel turn at WrestleMania 17, Angle became the top babyface as Rock started to wind down his pro wrestling career and transition to movies.

Angle did have an ego to go along with his credentials, as he always considered himself the toughest guy in the locker room. And perhaps he was, but his ego was more self confidence than anything, and it’s not like he was unpopular backstage. Everyone knew he could take down anyone with ease, and it was very difficult to take him down as well.

After a tour of Europe, Angle was flying back to the US from England, talking with Vince McMahon. Vince reminisced about the time he took Angle down during a planned television angle, and as part of the angle, he jumped out of the ring yelling “two” like they do in amateur wrestling. Vince had done some wrestling in college and joked that he was the only one to ever take Angle down (even though it was part of the script).

Vince and Angle had an hourlong conversation talking about life, and as he got up to leave at the end, he turned around and again joked, “Remember Kurt, I’m the only one who’s ever been able to take you down.” With that, Angle got up, attacked Vince from behind, knocked him down, turned him over, and jokingly pinned him in the aisle. There were almost 100 WWF staff members on the plane and they were all laughing. It was clearly all in fun and everyone knew it.

Everyone except the Undertaker.

The Undertaker was asleep, and the noise and commotion had woken him up. When he woke up, he saw Angle on top of Vince. Angle had jokingly stayed on top of Vince for about 30 seconds as Vince tried to get him off. Not knowing it was just horseplay, Undertaker came from behind and choked Angle unconscious.

Angle blacked out for a full minute, and when he came to, Vince was standing over him with a big smile on his face.

Undertaker apologized to Angle, saying he didn’t know and that he was just doing what any good employee would do. Angle respected Undertaker as a locker room leader and totally understood.

For the next four hours on the plane, Vince tried to take Angle down any chance he got. It became sort of a competition, like a joke that never seemed to end. After a long, grueling tour, it’s not unusual for wrestlers to let off steam on the plane and for incidents like this to happen.

Vince would do things like attack Angle from behind and wait until he got out of the bathroom and charge him. Half the time, Angle never saw him coming. In one takedown, Vince hit him pretty hard, knocking him backwards, and he hit his face on the ground. Angle then got up, attacked him, took him down, and held him down for awhile. Then they’d hug before going back and forth doing the same thing the rest of the flight.

Everyone on the plane got a kick out of it. Undertaker remarked to Angle that, “You’ll never see Bill Gates doing this with any of his employees.”

The whole ordeal wasn’t really a fight, but the chokeout was very real and that’s why this incident belongs on our list. As tough as the Undertaker is in real life, if he and Angle squared off at the time in a legit fashion, there’s little doubt Angle would’ve taken him apart, and Undertaker would be the first to admit it. Well, maybe not the first, but he’d admit it.