The greatest character ever created by Vince McMahon, The Undertaker was a three time WWF™ World Heavyweight Champion between 1991 and 1999, and was one of the promotion's most recognizable stars.

Born Mark Calloway, Undertaker feuded with every top star in the WWF™ during the ' 90s, helping the promotion survive through lean business periods in the wake of the steroid scandal of 1992 and Vince McMahon's subsequent federal indictment in 1994. Calloway first entered pro wrestling in the late ' 80s, for a while languishing in the southern territories under a wide range of gimmicks and names, such as "The Master of Pain" and "The Punisher". He won his first major regional title on April 1, 1989, when he defeated Jerry Lawler for the USWA™ world title in Memphis.

He landed in the NWA™ in 1989, where he was billed as "Mean" Mark, forming The Skyscrapers with Sid Vicious and feuding with the Road Warriors and the Steiner Brothers. The he teamed with Danny Spivey after Vicious suffered a serious injury, before going on to singles matches, challenging then U.S. Heavyweight Champion Lex Luger at the Great American Bash™ pay-per-view.

Calloway was released from the NWA™ in a cost-cutting measure and debuting as The Undertaker at the WWF™ Survivor Series™ on November 22, 1990. He was a stoic figure dressed in dark clothingwho moved slowly and deliberately in the ring, and initially said only a few words in interviews, as manager Paul Bearer did bulk of the speaking for him.

One year later at Survivor Series™ in ' 91 in Detroit, he defeated Hulk Hogan for his first WWF™ World Heavyweight title, but dropped it back to Hogan a week later. It would be another five years until he won his next title. Until this time, his feuds with Hogan, Randy Savage, Steve Austin, The Ultimate Warrior, Bret Hart, Shawn Micheals, and Mick Foley helped The Undertaker become one of the greatest icons in WWF™ history.

By the time he won his second WWF™ World title, he had become one of the promotion's top babyfaces. He defeated Sid Vicious on March 23, 1997, in the main event of Wrestle Mania 13™. His third title reign came on May 23, 1999, when he defeated Steve Austin in Kansas City. Sadly, the victory was overshadowed by the tragic death of Owen Hart earlier on the card.

By the time, The Undertaker had dropped the "Dead Man" gimmick and managed to reinvent himself as a trash-talking biker, straddling the fence between babyface and heel, and getting over with a new generation of WWF™ fans.