#2 The Master of Pain
Even back in 1989, The Undertaker was wrestling as a vicious and scary Superstar. Never was this more evident than his time in USWA, where he wrestled under the gimmick of The Master of Pain.
In this gimmick, The Master of Pain was supposed to be a character who had just been released by the United States Penitentiary, Atlanta. He had supposedly been imprisoned for five years for killing two men.
While wrestling in this gimmick, he was managed by Dutch Mantel and challenged Jerry Lawler, the then-USWA Unified World Heavyweight Champion. He defeated Lawler and thereby won his first-ever wrestling Championship.
#3 'Mean' Mark Callous
Before he joined WWE, for one very short year, The Undertaker wrestled in WCW in 1989 and 1990. He was known as 'Mean' Mark Callous, a name that was devised by Terry Funk.
Jim Ross described Callous as having a fondness for pet snakes and that he loved the music of Ozzy Osbourne. He wrestled as part of the Skyscrapers for a short while, before he joined Paul E. Dangerously aka Paul Heyman and defeated Johnny Ace as well as Brian Pillman.
However, his time here was short and after he was discouraged and told that no one would pay to see him wrestle, and he reconsidered his future. Heyman helped The Undertaker and soon enough he would prove everyone wrong as he made his way to WWE, which was then known as WWF.
During his time in WCW, he also briefly wrestled in Japan, as Dice 'The Punisher' Morgan.
Eventually, he found success in WWE as The Undertaker, and the rest, as they say, is history.