#1. Vince McMahon and The Undertaker had real-life heat at one point
Vince McMahon and The Undertaker are famously close friends in real life. But just like any other long-term friendship, The Deadman and McMahon's relationship has seen a few ups and downs.
After the infamous Montreal Screwjob at Survivor Series 1997, The Undertaker became livid after he learned about McMahon's role in the whole situation.
Charlotte Flair to return and wrestle a CURRENT CHAMPION?
During an appearance on The Bill Simmons Podcast, The Undertaker said he even confronted the Chairman and CEO of WWE the following day on Monday Night Raw.
"'If this kind of s**t happens again, you've got to involve me here, because it doesn't have to go down like this,'" Undertaker told McMahon.
"And he [McMahon] agreed. I guess it all worked out. It was sad. I'm really tight with Bret. Bret could've done some things differently; Shawn could've done things differently; Vince could've done things differently."
Another story about The Undertaker and McMahon dates back to the period after WWE Crown Jewel 2019. The Undertaker was scheduled to attend Starcast II, a mini-convention during the weekend of Double or Nothing 2019.
In chapter four of the docuseries, The Last Ride, The Deadman said he was unaware that AEW’s first-ever pay-per-view event, Double or Nothing, would run parallel to his autograph signing event.
Apparently, this didn't sit well with Vince McMahon, who called up The Undertaker to discuss the whole situation.
“Vince and I had a little bit of a falling out over it, and I understand where he was coming from. He’s got a business to run. I understand his position."
Both men didn't talk to each other for a while, but this incident didn't derail their longtime friendship as The Undertaker and McMahon eventually sorted things out.