Flair recalled how he lost a Rolex watch while out partying with The Undertaker and former NBA player Harvey Grant. They were apparently joined by everyone's friend Jack Daniels.
"I'll shoot him a text and joke around," The Nature Boy said of his relationship with The Deadman. "We didn't hang around every day but when we're together know we have fun! [laughs] He knew how to get the best out of me! He runs from me now because he knows!
"I lost a Rolex with Taker one night [laughs]. Oh God, Horace Grant with the Bulls - every time I see that Last Dance field. Horace has got a brother Harvey who plays for the Bullets. We and Taker and Harvey Grant were out one night - and I lost a Rolex, which is a whole different part of the story [laughs]. Trying to hang with him and that Jack Daniels man, it's tough. We've had so much fun!"
Flair first met Mark Calaway back in 1989 when Calaway was teaming with Dan Spivey as The Skyscrapers. While they weren't close friends then, Flair said he immediately saw the talent and potential in the rising talent who would become The Undertaker.
"Obviously you recognize the unbelievable athleticism of this guy that is 6-10, over 300 pounds," Flair said. "It's just a matter of time whether he finds that bit or somebody finds it for him, that guy is going to be something in this business."
Flair would return to WWE in November 2001 and face Taker just a few months later at WrestleMania 18. Flair said he was just a shell of himself when he stepped in the ring with Taker on The Grandest Stage of Them All. Flair recalled how nervous he was that night at the SkyDome in Toronto.
"When I agreed to come back to work it was never to wrestle," Flair revealed. "I just look back and say, 'God if I could have just gone into the ring and felt like I did when I walked out, so much better it could've been.' I was so nervous wrestling Taker - when anybody in the world would be so excited to walk down that ramp and I was horrified."
He continued, "Once we got going - and he knew, I told him, it's hard to tell somebody, 'I'm struggling.' Well, Ric Flair's got a problem guys. I've always been so comfortable with him, I had no problem telling him. And he got it."
Taker would go on to defeat Flair in their No DQ match at WrestleMania X-8 that night, which went almost 20 minutes. Flair will appear in Sunday's Chapter 4 of "The Last Ride" on the WWE Network.