The Deadman Arrives (1990–1994)
A short time later the Undertake was given to Paul Bearer from Brother Love. Paul Bearer would accompany the Undertaker to the ring brandishing an urn from which the Undertaker seemed to draw mystical powers. During his instal run as a heel, after defeating his opponents he place them in a body bag and carry them to the back.
Following this he would have small feuds with Randy Savage, Sid Justice, Sgt. Slaughter, and Hulk Hogan. At the Survivor Series he defeated Hogan to win his first WWF Championship with help from Ric Flair. At the time he was the youngest WWF Champion in history. WWF President Jack Tunney would order a rematch six days later at This Tuesday in Texas in which he lost the title back to Hogan.
With the help of several villainous wrestlers Yokozuna won the match sealing the Undertaker in the casket. After the match the Undertaker's “spirit” appeared on the video screen warning that this wasn't the end of the Undertaker and he would return
The Return and Mankind (1994–1997)
Following the conclusion of the Alliance angle, the Undertaker would once again turn heel. Shortening his hair and calling himself Big Evil. At Vengeance, the Undertaker defeated Rob Van Dam for the Hardcore Championship.
The Undertaker would then move on to feud with the Rock. This feud carried on from the Royal Rumble all the way until No Way Out where the Undertaker lost due to interference by Ric Flair. The Undertaker upset challenged Flair to a match at WrestleMania X8. Initially Flair refused till the Undertaker begin taking out those close to him, first Arn Anderson, then Flair's son David Flair. After the Undertaker threatened to do the same to Flair's daughter, Flair accepted. The Undertake would go on to defeat him at WrestleMania that year.
After winning the number one contendership for the world title, the Undertaker would go on to defeat Hulk Hogan for the belt. The Undertaker would go on to turn face again following a brutal match with Jeff Hardy which he raised Hardy's hand after defeating him. The Rock would later win the belt away from the Undertaker.
The Undertaker started a feud with Brock Lesnar. The rivalry would see them firth at Unforgiven and in a Hell in the Cell match at No Mercy. Following the lost to Lesnar the Undertaker would then go on another hiatus after being thrown off the stage by the Big Show.
At the Royal Rumble the Undertaker returned to restart his feud with the Big Show. The Undertaker would go on to defeat both the Big Show and A-Train in a tag team handicap match at WrestleMania XIX.
Back to the Deadman (2004-2007)
Prior to WrestleMania 21 Randy Orton challenged him to a match. Randy Orton using his Legend Killer character threatened to end the Undertaker's undefeated streak at WrestleMania. Even with help from Cowboy Bob Orton, Randy was unable to defeat the Deadman at WrestleMania, losing and bringing the Deadman's streak to 13-0. For most of the remainder of the year the Undertaker would continue on with his feud with Randy Orton. The competed in a casket match and a hell in a cell match throughout the course of this feud. After his Hell in Cell win at Armageddon the Deadman would take another hiatus from wrestling.Starting from the Royal Rumble and going into WrestleMania 22, the Undertaker found himself involved in a feud with Mark Henry after he cost him several championship opportunities. The Undertaker would once again emerge victorious and keep the streak alive for another year.
The Undertaker would then begin lengthy program with Mr. Kennedy. Kennedy cost the Undertaker two World Heavyweight Championship opportunities. The Undertaker and Kennedy would continue to feud going into 2007.
After attempting to get some retribution against Vickie Guerrero he begin a feud with the Big Show who interfered on Vickie's behalf. The two would go on to feud for several months leading into the first part of 2009.
Soon after the Undertaker was confronted by Shawn Michaels who wanted to end the Undertaker's WrestleMania streak and pointed out that up to that point the Undertaker had never defeated him in a one on one match. In what would be the match of the year, the Undertaker defeated Shawn Michaels to keep his winning streak intact. He would go on another long hiatus after the Wrestlemania match.