For 34 year old World Wrestling Federation Champion, "The Undertaker", who began his quest to become a superstar in late 1985 at the young age of 22, it has certainly been a rocky-road to the top.
Mark Calaway began his career like most do, working independents, and regional territories for pennies, in hopes of being noticed and making that journey to the big-time. In 1985-96 Calaway began working for the Memphis based promotion, USWA (United States Wrestling Association). Calaway was brought in by Jerry Lawler (The co-owner of the USWA) to be part of one of wrestling's oldest formulas (of which Lawler has used some 60-70 odd times). Calaway would play the role of lead "monster heel" to Jerry Lawler's equal role of "babyface champion." Calaway was quickly pushed to the top of the Memphis-based USWA, but not as himself, rather as "The Master of Pain." "The Master of Pain" eventually defeated and destroyed Jerry Lawler. It led to the eventual super-hero comeback that Lawler had pulled off so well so many other other times in the past. Eventually, Lawler did make that super-hero title victory over Calaway and Calaway's run as super-heel was over in the USWA.
At the same time that Calaway was working that Memphis-based version of the USWA, he was also working for the Dallas-based version of the USWA. But he was not wrestling in Dallas as himself either, but instead was brought in again as the "monster heel." This time, with a mask and known throughout the territory as "The Punisher." Calaway was in the same basic role that he'd been given to by Lawler. While Calaway was working for the Dallas-based USWA, someone in the WCW (World Championship Wrestling) discovered for WCW that Calaway had a lot of untapped wrestling potential for a performer of his bulk.
Calaway would soon make his WCW debut and had finally reached where the "Big Boys Play" (well, that slogan didn't come until a few years down the line, but you get the idea). It was certainly a dream come true, as one would expect that it should be for any aspiring wrestler on the independent scene. Although, this time Calaway was stripped of everything that had in the past made him successful in wrestling. He wasn't hired by the WCW to be the lead "monster heel." He was hired to fill in on the middle-card matches and allow WCW to have more talent-depth. The established performers in WCW were already engraved in stone, and as many would come to know, it was hard to get a decent push in WCW, unless you "were the son of someone, or you knew someone" (thanks to Kevin Nash for this quote on Nitro) that was carrying the pencil. WCW decided to go away from any gimmicks for Calaway and renamed him "Mean" Mark Callas. WCW figured that he did not need a gimmick, and that he could get himself over with his ability. It wasn't lack of ability which would steadily create Calaway's career to start to look like it would never go past mid-carder status. It was Calaway's lack of experience as anything other than a "monster heel." WCW had taken everything that Calaway was familiar with him away from him, and basically he stood next to no realistic chance to survive in WCW. Calaway was quickly repackaged and put into a "monster heel" tag team managed by Paul E. Dangerously. The team was known collectively as "The Skyscrapers." Danny Spivey was the other half of the futuristic "monster heel" tag team. The team was headed to the top of WCW, but one could argue that all of the politics that were involved in WCW at the time of the team's rise, more than likely would have kept them from ever reaching the top. For Calaway, at the same time, probably the greatest thing that possibly could have ever happened to him happened.
Calaway's contract with WCW expired. Oddly enough, the year was 1989, and coincidentally the WWF (World Wrestling Federation) was left scrambling to find a new "monster heel," upon Barry Windham walking out on his contract. With Windman gone and out of the picture, executives at the WWF were left in a frantic frenzy to find a replacement. However, there is no real way for anyone to find out just how Calaway was decided upon to be brought into the WWF as "The Undertaker," or for that matter how the character was even actually created, but that really doesn't matter in hindsight. Calaway debuted as "The Undertaker," written in the WWF storylines as being found by former WWF heel manager (and now WCW manager) Ted Dibiase. Calaway was a perfect fit for the role which was obviously developed to be a "monster heel." Calaway finally came full-circle and was working for a BIG LEAGUE promotion in a role that would allow him to use all of the tools that he was familiar with to get himself over. "The Undertaker" was an instant hit and had no problems at all at reaching the upper-echelon of superstars in the WWF. Although, it would not be for a few years after he debuted in the WWF that he would be put into a feud with Hulk Hogan, that would lead to him capturing the WWF title for the first time. Although, the political climate in the WWF was probably much worse that it was in the WCW, it still caused Calaway's title win to be a backdrop to Hogan regaining the belt back a few days later.
Six years later, still wrestling in the WWF as "The Undertaker" but now in a position where he doesn't really need the character to get over, and can get himself over with his share in the ring abilities. "The Undertaker has gone through a lot of changes since he first debuted. The gimmick has become less and less of a gimmick as the years have gone by, and has more or less become an extension of Calaway's out of the ring life. Calaway has been in the WWF for so long that he has seen the changing of guards a few times, and has seen the politics change drastically. At Wrestlemania 13, Calaway finally reached the top of his profession and won the WWF title from "Sycho" Sid (ironically, it was Sid who replaced "Mean" Mark Callas all those years ago in "The Skyscrapers" when Calaway opted to leave for the WWF). For all concerned, this may be Calaway's second title reign, but when you come right down to it, it is more like his first. Only because this around, there are no super-hero's in the background waiting to leg drop him for the three count. It would seem the only other possibility and change that "The Undertaker" should eventually go though, if the metamorphis is of "The Undertaker" to Calaway. But, at this point, it is hard to tell if Calaway even exists anymore, or for that matter if "The Undertaker" even exists anymore.