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There were people in WWE that didn't believe there would be a natural chemistry between the Deadman and the Heartbreak Kid and it wasn't seen as "something that was necessary from a product standpoint".
The two weren't even particularly close behind the scenes and the Undertaker has even opened up about his hatred for Michaels back in the day.
But under the lights Michaels felt a special type of energy with "gifted" 'Taker' from the off.
In fact, their connection became so strong that they did not need to follow a script when mixing it up in front of sold-out crowds. They relied on instinct and feeling it in the moment.
"We got in the ring together and it was unbelievable," the WWE Hall of Famer told SPORTbible in an exclusive interview.
"I feel like I could have done it with my eyes closed and known exactly where he was going to be.
"Every now and then you get in the ring with guys and it's perfect. He was one of those individuals.
"Usually that happens with your friends. I've had it with Hunter but you sort of expect that because you spend time with each other.
"Mark and I were very much two guys that were individuals away from each other. We didn't share a lot in common or talk a lot and so to have chemistry with someone like that, I couldn't help but notice and think to myself, 'Ha, I never saw that coming'."
"You knew what one another was thinking and what we wanted to do. Sure, you could have your bullet points here and there but how you were going to get there was trusting the other guy to be there. We had that from the get-go."
The two went at it in the first ever Hell in a Cell match way back in 1997 at 'Badd Blood', an event that marked the terrifying debut of Undertaker's brother, Kane.
But it was more than ten years later when they produced sports entertainment poetry on 'the Grandest Stage Of Them All'.
Michaels and Undertaker delivered back-to-back classics at Wrestlemania 25 and 26, with HBK retiring after the second consecutive failed attempt at ending the Phenom's coveted undefeated streak at the show of shows.
Yet the story was not finished there as Michaels' best friend and DX tag team partner Triple H challenged 'Taker' in his yard at the two Wrestlemanias that followed in 2011 and 2012 respectively.
For the second bout, inside Hell in a Cell, Michaels was the special guest referee as Taker once again emerged victorious in an an emotional encounter.
In many ways, the "End of an Era" story built was a perfect one.
"I thought it was phenomenal," Michaels reflected.
"That was a four-year novel, a four-part movie series. You could do the creative WWE storylines but there was enough real life attachment and relationship that people knew behind the scenes, that made it even more special.
"They [the WWE Universe] can see the real human beings behind these characters telling another sub-story of this respect but competitive nature between these individuals.
"When you have all those combinations when the emotions are really there, they just accentuate the on-television story that you're also telling.
"When we sit together and talk about the journey we've shared together over the last 25-30 years, it was in that four-part series and it was all very real.
"A lot of it was not discussed or talked over. It was just in the moment, us honouring one another for the friendship and the professional friendship. A very real moment in the world of WWE."
You simply couldn't fake the natural emotion that came afterwards. The three men shared a special embrace on the ramp in what has become one of the most iconic images in wrestling.
"We've all got that picture. There are a some of us who don't have a room decorated full of wrestling stuff but you can darn sure bet that picture is in there because it doesn't have anything to do with wrestling.
"It happened to take place at our job but it's the story we told. The three of us have spent more time in a locker room with one another, with professional ups and downs - than we've spent with our prospective spouses and families!
"There's a brotherhood there and something that goes beyond what I would say is a normal friendship and bond."
On Sunday, 30 years after his debut at Survivor Series in 1990, one of the all-time greats bids farewell to a business he has given so much to.
He's left his blood, sweat and tears on the canvas and now, 'Taker', real name Mark Calaway, will heave his hat, gloves and trenchcoat in the ring.
But what made the 55-year-old the most complete performer in WWE history and what will his legacy be?
"It was having an absolutely phenomenal character but embracing it," Michaels stated.
"I personally don't recall anybody giving him tips on what he should do.
"I don't remember hearing anything like that because he was so in tune with what he wanted to do with that character.
"If you look at the fact it's lasted 30 years, no-one can argue that he was an absolute master at it because he knew what that character and person was going to do.
"He was unbelievably juidicious with what he did with it - slowing peeling back those layers in a very systematic and careful way. That is an absolute art in itself.
"It is hard not to marvel at what he's done over the last 30 years. I think, and he would tell you, we don't care where anybody ranks but he knows where he ranks with us and that is easily one of the absolute best guys to be in that ring with.
"A lot of us are thrilled for him, admire the heck out of him and just want to help him celebrate and enjoy this moment - not just what he's done for WWE but the careers of countless guys."
Taker looks set to ride off into the sunset before his inevitable Hall of Fame induction. Whatever his next move is, Michaels, one of his greatest rivals on screen, wholly supports him.
"We haven't had the opportunity to sit and chat about that but like with a lot of things, he keeps a lot of things close to his chest.
"It's his decision. I don't care if we celebrate 30 years and two weeks later he decides to have a match against somebody. He can do whatever he wants, he's earned it.
"I'm thrilled if he does and equally if he doesn't. He loves this line of work, everything about what he's done shows that and I think we just appreciate what he's given us and let him conduct himself as he chooses."
WWE Survivor Series is live on BT Sport on 22 November.
Featured Image Credit: WWE
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