World Wrestling Federation/Entertainment

(1990-1994)

Calaway debuted in the World Wrestling Federation as The Undertaker on November 22, 1990 at Survivor Series 1990 as the mystery partner of Ted DiBiase's Million Dollar team. About 1 minute into the match, Undertaker eliminated Koko. B. Ware with his finisher, called the Tombstone Piledriver, which after he would cross his victim's arms on the victims chest to pin. After Survivor Series, Calaway was also called Kane the Undertaker at several shows until "Kane" was dropped from his name, and he reverted back to simply "The Undertaker." Kane later became the name of his character's half brother.

The appearance of Undertaker was modelled on that of a mortician from old Western movies, with the character being supposedly impervious to pain and possessing supernatural powers, such as teleportation and manipulation of flames and lightning. It was also at this time that the Undertaker switched managers from Brother Love to Paul Bearer.

In 1991, the Undertaker's popularity grew rapidly. He made his WrestleMania debut at WrestleMania VII, defeating the legendary "Superfly" Jimmy Snuka. After an undefeated year and high-profile feuds with Ultimate Warrior, Randy Savage, and Hulk Hogan, he defeated Hogan at Survivor Series 1991 to win his first WWF Championship. However, due to interference from Ric Flair, the WWE President Jack Tunney ordered a rematch. He lost the title six days later to Hogan at Tuesday in Texas. Between December 1991 and September 1993, the Undertaker did not lose a singles match.

Early in 1992, he had a falling out with ally Jake Roberts. After Roberts lost a match on Saturday Night's Main Event to Randy Savage, Roberts planned on attacking Savage and his manager/wife Miss Elizabeth with a steel chair. Undertaker prevented this from occurring, thus turning face. He went on to defeat Roberts at WrestleMania VIII. He feuded extensively with wrestlers managed by Harvey Wippleman throughout 1992 and 1993, most notably Kamala and Giant Gonzales. He defeated Gonzales by disqualification at WrestleMania IX and then pinned Gonzales at SummerSlam 1993.

In January 1994, he challenged then WWF Champion Yokozuna and met him in two of the best known casket matches in WWF history at the 1994 Royal Rumble and Survivor Series 1994. At Survivor Series, Chuck Norris was special guest referee. At the Royal Rumble, Yokozuna sealed Undertaker in the casket with the assistance of multiple other heels. The Undertaker's "spirit" appeared from inside the casket on the video screen, warning that he would return. This began Undertaker's first hiatus. In reality, he had a back injury that was getting worse, and he needed time off. An Undertaker "clone" appeared after WrestleMania X, played by Brian Lee and led by Ted DiBiase. This led to the resurrection of the real Undertaker and an epic battle at SummerSlam 1994, where the real Undertaker was victorious.