5 superstars who faced Mr. McMahon in the ring

Mr. McMahon is an apex authority figure in WWE. He oversees everything the company has done in nearly four decades. The former ECW Champion is also a very hands-on boss, as evidenced by his occasional in-ring appearances and matches.

McMahon is willing to do anything for the business, even at the ripe age of 76. From getting busted open to dancing for fans, there isn’t anything he wouldn’t do for the WWE Universe.

It is thus a remarkable moment when the CEO steps into the ring to do battle with his employees. Over the years, he has competed in the squared circle when the time and storyline have called for it. While most of them have resulted in the boss taking a beating, it has never failed to entertain.

The wrestlers he has stepped into the ring with are all his most trusted associates. Some of them were purely for show, while others required a grudge match to prevent the bad blood from boiling over. Whatever the circumstances, anything trying to outdo a McMahon in-ring appearance has got no chance in hell.

Here are five superstars who have had the pleasure of sharing the ring with Mr. McMahon.

#5 On our list of 5 Superstars who faced Mr. McMahon in the ring: Bret Hart

Wrestling fans need no introduction to the history between Bret Hart and Mr. McMahon. How WWE’s owner screwed the Excellence of Execution in Montreal remains one of wrestling’s ugliest tales.

Many years later, Hart and McMahon buried the hatchet, with the former even appearing on Monday Night Raw. Unfortunately, Vinnie Mac couldn’t let go of his ego and ticked the Canadian off so much that he demanded a match to settle the score.

McMahon was tricked into accepting the challenge and was scheduled to do battle at WrestleMania XXVI. Although he thought he had paid the Hart family to screw Bret again, The Chairman ended up taking a beating from the entire clan. It culminated in the Hitman locking in the sharpshooter and forcing his nemesis to tap out.

4 CM Punk and Mr. McMahon get personal and physical

CM Punk was on top of the WWE in 2012. Towards the end of the year, he turned heel and rubbed many people off the wrong way, including McMahon himself. The Chairman and the then-WWE Champion agreed to a Street Fight on RAW.

Punk attacked McMahon from behind before the match even began. He dominated the early proceedings until his resilient opponent turned the tables. He sent him crashing into the announce table and beat him up with a kendo stick as the crowd roared their approval.

The Best in the World recovered and set McMahon up for the GTS. However, the arrival of Ryback and John Cena forced him to retreat.

#3 Father and son battle ‘Stone Cold’ Steve Austin

Back in 1999, a series of events led to ‘Stone Cold’ Steve Austin being appointed the CEO of the WWE (then WWF). Naturally, this didn’t sit well with McMahon, who accepted a challenge from the new boss to determine who the CEO of the company would be.

It was announced that a Handicap Ladder match between the Texas Rattlesnake and McMahons would decide the fate of the company. The contract was then suspended in a briefcase above the ring for the wrestlers to try and take.

In the end, the numbers proved to be too much for Austin, who lost the match to the father-son duo. However, he would continue to be a thorn in the side of the evil McMahons, especially that of Mr. McMahon.

#2 Mr. McMahon wrestles his own daughter

Even though the Attitude Era was all sorts of crazy, Stephanie McMahon being beaten up by her own father was a different kind of madness.

Back in 2003, the young woman’s decisions as SmackDown's General Manager didn’t sit well with McMahon. The subsequent feud resulted in the highly controversial ‘I Quit’ match between the pair. It was sickening to see the kingpin assault his daughter despite the latter’s fightback.

Eventually, however, the sight of McMahon choking Stephanie was enough for his wife to throw in the towel, awarding the victory to her husband.

#1 Mr. McMahon tries to bury The Undertaker alive

The 2003 feud between McMahon and the Undertaker escalated to a personal level thanks to the former’s actions. Despite trying his best to screw the Reaper, he prevailed and won the right to challenge him to a match at Survivor Series.

'Taker announced that he would be battling McMahon in a Buried Alive match. He took special pleasure in beating his opponent up and did enough to secure the win. However, interference from his brother Kane meant he was ultimately the one buried alive.

Who was your favorite superstar going up against Vince McMahon? Sound off in the comments below.