Another difficult decision.
Both of these men are the two greatest wrestlers in the history of professional wrestling. The best performers, the best innovators, the best storytellers of all time. Alone, they're phenomenal without a doubt but every time they step inside the ring together, one on one, they create poetry that's unlike anything ever seen in a wrestling ring and they both have won the PWI Match of the Year award twice to prove it, not to mention having arguably the most compelling Royal Rumble finish ever at the 2007 Royal Rumble. With both of them, you tend to forget that what you're watching is predetermined. The cynicism, that we smarks tend to carry with us as we view at matches, is completely subdued from the ring of the first bell to the very last one because of their ability to captivate the hearts of anyone who's fortunate enough to see them perform. But who do I believe is the better man?
Let's take a look at the career of Shawn Michaels? Ask yourself this, if someone out of the WWE's current tag teams, were to go solo, how many of them would you believe would have half the fabled and illustrious career that Shawn Michaels had? I didn't think so.
During the late 80's/early 90's, as a Rocker, he stole the show time and time again as he broke the mold from the usual wrestling styles during the Golden Era. Then, after he went solo, he showed us all what he was able to do by himself and boy did he impress. From his Ladder match with Razor Ramon, to his Iron Man match with Bret Hart, HBK began to show the world why later on in his career, he was known as Mr. Wrestlemania, one of the most fitting monikers ever in this industry. Unfortunately, a back injury cost him 4 years of his career but that didn't stop him from making a comeback and steal the show every time he went in the ring at Wrestlemania, from HBK v. Kurt Angle to his last few classics with The Undertaker. And ironically, it was the period AFTER his injury that most people tend to give their respect for Mr. Hickenbottom which basically means that after a career debilitating injury, Michaels got better than he ever was before but the common theme, that separated himself from everyone else, was his storytelling. No matter what match he was in, he could sell, pain, heartache and triumph like no other and drew everyone into all of his actions with his ability to convey emotion better than anyone he competed against. Every blink, every breath, every twitch gave his matches more depth and weight no matter how slight. In his aging years, Shawn Michaels may not have been able to "send chills up and down their spines" with a wink and a smile anymore, but he did it in all of us simply by captivating the hearts of millions of wrestling fans all around the world by giving his heart out and never being out of pace.
A mortician that has the ability to warp the lines between fantasy and reality, defies the laws of physics and logic, has unearthly immunity to pain, control over lightning and can resurrect from death at will? Sounds like something that Jack Kirby would write up, huh? Without even analyzing The Undertaker's career, could anyone honestly say that this kind of gimmick would work for anyone in wrestling. For Mark Calloway, he made it work and because of said gimmick, became the most respected and iconic entity in wrestling and has remained so for the past 22 years. From the first gong at the Survivor Series 1990, everyone's eyes were glued to The Undertaker from the start. His amazing athleticism, for a near 7 footer and 300 pounder, and his ability to sell his gimmick through his promos, mannerisms and matches made The Undertaker a main eventer merely a year after his debut when he won the WWF Championship from Hulk Hogan. It's quite rare for people to accept someone getting a push to the moon all while not getting bored by them at all. Simply because of his awe-inspiring presence, The Undertaker proved himself worthy of being able to hang with the big boys and did so with every single incarnation of his persona. Like HBK, his storytelling was top notch though he had to rely more on "props" than Michaels did. However, his threshold of pain, his undying will, is one of his many admirable traits. His body degenerated more and more as the years went by but that never stopped him. No matter how legitimately broken he got, The Underkaer would never throw in the towel. Even getting set on fire at the Elimination Chamber didn't stop him. Like Michaels, The Undertaker was able to innovate himself and basically had no choice as he had to deal with different versions of himself over the past two decades, never letting one incarnation get tiring or boring and has commanded the respect of countless wrestling fans from different generations.
So, with all of that said, the person to get my vote is The Undertaker. Why?
It all comes down to one thing: respect. It's been noted that Shawn was a huge prick back in the day and would always throw fits whenever he didn't get his way. Not to mention him trying to bury other up-and-comers and refusing to go over anyone. He was selfish. Absolutely selfish and Michaels may have cleaned up his act, but that doesn't erase how egotistical he was and how he would never consider giving anything back to the company that provided him with the platform to become a star.
The Undertaker? Nothing but respect for him. He was the locker room leader for most of his career and was looked up to by everyone because of how humble he was and because how he was able to stick up for the younger guys and for any injustices in general. The story about how Undertaker had to threaten HBk to put over Austin at WM 14 is a prime example of how Undertaker wouldn't take any shit in the back and people respected him for that. He even stuck up for Bret after the Screwjob occurred, getting right in Vince's face for it. Flair even noted that during his feud with Taker, backstage, Mark would refer to Flair, 16 time world champion, as kid. You don't get anymore respect than that in my book.