5 Top WWE Superstars who had an awkward first meeting with Vince McMahon

#1. The Undertaker - Vince McMahon had "nothing" for him in their first meeting

The Undertaker and Vince McMahon

The Undertaker is the greatest character that Vince McMahon ever created and there's no disputing it. In an era where superstars got gimmicks selected randomly from a box, The Phenom stood the test of time to become an immortal in the wrestling industry.

In his prime, there was no wrestler in the world more respected than The Undertaker. A legend and locker room leader, he had a presence and authority about him.

But years before he was the most respected man in wrestling, The Deadman was in an extremely tricky position. He wrestled in WCW before, but the higher-ups told him that people would never pay to see him. Stating that it only made the chip on his shoulder grow, he sought out to sign with WWF/E through his connections with Paul Heyman (his manager) and Bruce Prichard.

While Vince McMahon wasn't impressed with "Mean" Mark Callaway at first, he relented to Prichard's requests and met The Undertaker. The Phenom told Peter Rosenberg on his Cheap Heat podcast that his first meeting with the WWE Chairman ended awkwardly as there was nothing for him:

"I’m working in WCW without a contract. We finally went to the Meadowlands [Arena] I think, the next morning i had a meeting at [Vince’s] house. Even then, I went in thinking, I got this. I had the meeting, maybe two hours i spent with Bruce and Vince and JJ Dillon and Pat Patterson. I have this meeting and think i’m being impressive and charming. At the end of the meeting Vince looks at me and goes, ‘We don’t really have anything right now.’ (laughs). I already gave my notice thinking, I’ve got the meeting, the job’s in the bag, Ive already given my notice down at WCW,” said The Undertaker. (H/T SEScoops)

The Undertaker went on to reveal that Vince McMahon told him there would possibly be an opening after WrestleMania. After his involvement with Hulk Hogan in Suburban Commando (a movie that The Undertaker described as the "worst ever"), he got the call and eventually debuted at Survivor Series 1990.

Vince McMahon was looking for the right man to fit The Undertaker character, and Mark Callaway was it. The rest, as they say, is history.