The Undertaker debuted at the 1990 Survivor Series as the mystery opponent on Ted DiBiase's team. He was originally managed by Brother Love, but was soon turned over to Paul Bearer, who carried a mysterious urn that seemed to give UT supernatural powers. He is undefeated at WrestleMania matches, as he beat the great "Superfly" Jimmy Snuka in his first WM match, WrestleMania VII. He went on to feud with the Ultimate Warrior in several bodybag matches. He even managed to lock the Ultimate One in a casket in the summer of '91. By the time the Survivor Series had rolled around, UT established a win/loss record that got him a shot at WWF Champion Hulk Hogan. He beat Hogan at the Survivor Series with a Tombstone onto a chair. His celebration was short lived, however, as Hogan won the title back by throwing ashes in the Undertaker's face, and rolling him up.
In early 1992, The Undertaker turned against his friend Jake Roberts, and beat him at WrestleMania VIII. Because Jake was one of the WWF's most hated men at the time, UT's popularity rose. He got into a feud with Kamala, and beat him by DQ at SummerSlam. He went on to beat him in the first ever Casket Match at the Survivor Series, which prompted Kamala's manager, Harvey Wippleman, to bring in Giant Gonzales to test the Undertaker.
At WrestleMania IX, the Undertaker rode to the ring on a float with a vulture by his side in a memorable entrance, as he wrestled Gonzales. Gonzales was disqualified for smothering UT with a rag soaked in chloroform. Just before the King of the Ring, Gonzales and Mr. Hughes beat up the Undertaker and Paul Bearer, putting them out of action until SummerSlam, where Undertaker beat Gonzales in a R.I.P. match. These victories proved UT was once again in position for a shot at the WWF title, which was held by Yokozuna.
At Royal Rumble '94, UT wrestled Yoko in a Casket Match. UT lost, but it took nine guys pounding on him for about ten minutes to lock him in the casket. As Yoko's entourage pushed the casket up the aisle, the lights went out, and the Undertaker appeared on the video wall. He made one of his more famous speeches, and appeared to come out the top of the video wall, and ascend to the top of the arena.
"The spirit of the Undertaker lives within the soul of all mankind... the eternal flame of life that cannot be extinguished... the origin... of which cannot be explained. The answer lies in the everlasting spirit. Soon all mankind will witness the rebirth of the Undertaker... I will not rest in peace..."
After that, no one heard from the Undertaker for months, until Ted DiBiase claimed to have found him that summer. He had a man claiming to be the Undertaker (It was Brian Lee, or Chainz). Paul Bearer told everyone he contacted the real UT, and an Undertaker vs. Undertaker match took place at SummerSlam. The real Undertaker won, and the fake one left the WWF. UT's next order of business was Yokozuna, who he beat in a Casket Match at the Survivor Series.
At Royal Rumble 1995, UT wrestled I.R.S. (managed by DiBiase), and the Million Dollar Corporation stole Paul Bearer's urn, due to a distraction by King Kong Bundy. UT beat Bundy at WrestleMania XI. During the match Paul Bearer got back the urn, but it was stolen again by Kama, who melted it down and made a necklace out of it. Undertaker then feuded with Mabel, who he lost to in the first round of the 1995 King of the Ring, after Kama interfered. UT beat Kama in a Casket Match at SummerSlam but didn't get his urn back. He finally got it back on Raw by beating Sir Mo, Mabel's lackey, only to have it stolen again by Mabel. In a six man tag, he was injured by Mabel and Yokozuna. At the Survivor Series, he made his return and swept through Mabel's team. He beat Mabel at the December IYH in... you guessed it: A Casket Match!
Undertaker got a shot at Bret Hart's WWF Title at the Royal Rumble, but as he tombstoned Hart, he was attacked by Diesel, who thought that it was he who deserved the title shot. It was announced at WrestleMania XII, it would be Undertaker vs. Diesel, the WWF's two top big men at that time. Then the mind games started prior to WM. The Undertaker appeared and vanished right in front of Diesel's eyes. The next week, Diesel destroyed UT's casket. UT positioned a coffin at ringside, and when Diesel looked inside he saw a replica of himself. In a classic battle at WM XII, UT beat Diesel cleanly with the Tombstone. The next night on Raw, he was attacked by newcomer Mankind. Mankind interfered in Undertaker's matches all throughout the spring, which led to a match at King of the Ring. Seemingly by accident, Paul Bearer struck UT with the urn, allowing Mankind to apply the Mandible Claw and get the win.
At SummerSlam, they collided in a Boiler Room Brawl. After a brutal match, they made their way into the ring, where Bearer turned against UT and hit him with the urn, again, allowing Mankind to take the urn and win the match. At IYH: Buried Alive, a graveyard was constructed in the arena and the only way to win the match was to bury your opponent. UT eventually chokeslammed Mankind into the grave, but as he was burying him, The Executioner hit him with a shovel, and Bearer, Mankind, and Executioner buried the Undertaker. UT won a match against Mankind at Survivor Series, and won against the Executioner at IYH: It's Time. By the time WrestleMania XIII rolled around, UT was in position for another title shot. Finally, he got the title back by beating Sycho Sid. He proved himself a worthy champion, beating Mankind (IYH: Revenge of the Taker), Steve Austin (IYH: A Cold Day in Hell, and yes, he HAS beaten Stone Cold), Faarooq (King of the Ring), and Vader (IYH: Canadian Stampede).
He wrestled Bret Hart at SummerSlam and lost the title when Bret spat in the face of special referee Shawn Michaels. Michaels swung a chair in his hand at Bret who ducked and nailed UT. Bret made the cover, and got the title. UT wrestled Michaels at IYH: Ground Zero but that match failed to end decisively, which led to the first ever Hell in a Cell match at IYH: Badd Blood. Earlier in the year (About King of the Ring time), Bearer told everyone a story of how the Undertaker burnt his family's funeral home down, killing his family, including his brother Kane. When UT confronted him, Bearer told him Kane was alive, and coming to the WWF to face him. We saw Kane for the first time at Badd Blood, where he tombstoned UT, causing him to lose to Shawn. Kane then went on a rampage, tombstoning everyone, until Undertaker agreed to a match.
In December, Kane was confronted by seven of the people he had beat up earlier, and Undertaker helped him clean house! It seemed they had reached a truce, but then came the Casket Match at the 1998 Royal Rumble vs. Shawn Michaels. At the end of the match, Los Boricuas and The New Age Outlaws jumped in to help Shawn, and Kane came down and chased them off. Then Kane turned on UT, dumping him in the casket. Michaels then shut the lid, and Paul Bearer and Kane set the casket on fire. The Undertaker was nowhere to be found until a few weeks before WrestleMania, where a casket appeared on the stage, and was struck by lightning. UT emerged, and walked right through flames that shot up from under him. He agreed to fight Kane at WM XIV, where he beat Kane after three tombstones. He then beat Kane in an Inferno match at IYH: Unforgiven, where the ring was surrounded by fire. In May, UT walked out and demanded a title shot from Vince McMahon. McMahon told him he would get one if he could get past Kane, and the day after IYH: Over the Edge, they wrestled. Mankind interfered and cost UT the match which set up the now infamous second Hell in a Cell match at King of the Ring. UT won, but he had to throw Mankind off the top of the cell, chokeslam him through it, and slam him onto thumbtacks to beat him! He became the no. 1 contender to the title by beating Mankind, disguised as Kane. He teamed with Steve Austin to defeat Kane and Mankind for the tag titles last month, but they lost it back to them only a few weeks ago. He and Kane revealed they were indeed in cahoots, but he blew his big title match with Austin at SummerSlam. He and Kane both got a shot at Austin at IYH: Breakdown in a Triple Threat Match, where Kane and he pinned Austin at the same time. To decide the match, they wrestled at Judgement Day: IYH with still no conclusive winner.
Both Kane and The Undertaker participated in the Tournament at the Survivor Series. They met in the quarter finals (after receiving byes since they had been the no. 1 contenders) and UT beat Kane with help from Paul Bearer. However, he lost to The Rock by DQ, when Kane interfered, striking the Rock before he went after UT. Undertaker next went after Austin, and tried to embalm him alive. This prompted a Buried Alive match at IYH: Rock Bottom, which UT lost. After that, he disappeared for several weeks. In a seemingly unrelated incident, Dennis Knight was summoned to the arena by one only referred to as "He." The Acolytes attacked him and stuffed him into a car. A few weeks later, UT walked out on stage, flanked by Bearer, some druids, The Acolytes, and Knight. He made Knight part of his "Ministry of Darkness," renaming him Midian. The next victim was Mabel, who the Ministry attacked during the Royal Rumble, and again, stuffed him into a car. Next were The Brood. He had his minions set their sights on the Big Bossman, but they were unable to get him.
He beat the Bossman at WrestleMania XV in a Hell in a Cell match, and had the Brood hang him from the Cell. He also beat Ken Shamrock at IYH: Backlash. The Brood were the first to defect from the Ministry, because of UT's mistreatment of Christian. He merged the Ministry of Darkness with The Corporation forming the Corporate Ministry. With help from Shane McMahon, he beat Steve Austin at Over the Edge '99 for the WWF Title. He also revealed Vince McMahon as the Greater Power behind the whole Ministry as a ruse to get the title from Austin. He successfully defended the title at King of the Ring over The Rock, but lost the title back to Austin a night later. He lost to Austin in a First Blood Match at Fully Loaded, and soon after that, Shane McMahon broke up the Ministry. UT aligned himself with The Big Show against Kane and X-pac, and they won the tag belts from them at SummerSlam. They soon lost them to The Rock and Mankind, but won them back before losing them again to Rock and Mankind. Shortly before Unforgiven, The Undertaker walked out on the WWF when McMahon told him if he didn't participate in a match, he wouldn't get his shot at the WWF Title in the Six Pack Challenge.
He didn't return until May 2000 at Judgment Day, sporting a new "biker" look, and using Kid Rock's "American Badass" as his music. He came to the aid of The Rock during his Iron Man Match with Triple H. However, he ended up costing The Rock the title. He teamed with Rock and Kane to beat Vince and Shane McMahon and HHH at King of the Ring. He beat Kurt Angle at Fully Loaded. Soon after that, Kane turned on him once again and they battled to a no-contest at SummerSlam. He particpated in a Fatal Four Way for the Title at Unforgiven, against Kane, The Rock, and Chris Benoit but lost. He went for the WWF Title again at Survivor Series against Angle, but was once again unsuccessful. He participated in a six-man Hell in a Cell Match at Armageddon against Austin, Rock, Angle, Rikishi and HHH, but once again was unsuccessful.
He and Kane reached an agreement and formed an alliance for the Royal Rumble. Undertaker came close to winning, but was unsuccessful. He and Kane went for the tag team titles but failed to win them at No Way Out, losing a Table Match to The Dudley Boyz in a Triple Threat Match that also involved Edge & Christian. UT became angered at Triple H, who bragged that he had beaten everyone the WWF had to offer. He confronted Triple H, who wanted no part of the Dead Man. Undertaker beat Triple H at WrestleMania, and teamed with Kane to win the tag titles from Edge & Christian a few weeks later. With the new alliance of HHH, Stone Cold and Vince McMahon running roughshod over the WWF, UT and Kane stepped up to put a stop to it. They lost the tag belts to HHH and Austin at Backlash, in a match where Hunter's IC gold and Austin's WWF gold were also on the line. Undertaker received a title shot against Austin at Judgment Day, but failed to win. Over the next few weeks, a stalker showed footage of the Undertaker's wife Sara at their home. Undertaker was enraged and vowed to find out who was doing it. A week before King of the Ring, the stalker revelaed himself as WCW star Diamond Dallas Page, who merely wanted the Undertaker to "make him famous." They brawled in an unofficial match at King of the Ring, until Page ran from the arena. With WCW and ECW invading, Undertaker teamed with Austin, Angle, Jericho and Kane against DDP, Booker T, the Dudleys and Rhyno at Invasion. The WWF side lost when Austin went over to the Alliance. UT and Kane won the WCW tag team titles from Chuck Palumbo and Sean O'Haire a few weeks later as DDP and Kanyon won the WWF Tag Team titles. They beat them in a title for title cage match at SummerSlam, but lost the WWF belts to the Dudleys and the WCW belts to Booker T and Test a few weeks later. They beat Kronik at Unforgiven, and Undertaker beat Booker T at No Mercy. He teamed with Kane, Jericho, Rock and Big Show against Booker, Rob Van Dam, Austin, Shane McMahon and Kurt Angle at Surivor Series. The WWF won the match and banished the Alliance. Undertaker won the Hardcore Title from Rob Van Dam at Vengeance.
He targeted the Rock, after he cost him the Hardcore Title in a match with Maven. Undertaker beat Rock at No Way Out, and then went after Ric Flair, who he beat at WrestleMania. The WWF roster split took place in April, and Undertaker was surprisingly the first man drafted to Ric Flair's Raw brand. He was to get a title shot at Triple H at Backlash, but Hulk Hogan got it in his place. Instead, Undertaker beat Steve Austin at Backlash for a title shot at Judgment Day. Hogan won the title from Triple H, and Undertaker beat him for the belt at Judgment Day. Undertaker's match with Triple H took place at King of the Ring, and Undertaker won after the Rock got involved. In July, he defended against Kurt Angle, and a situation occurred in which Undertaker tapped out at the same time he pinned Angle. Angle said that a tap out took precedence and he should be the champion. The two met, along with Rock, in a Triple Threat match at Vengeance, in which Rock won the title. The Undertaker was then targeted by the UnAmericans, since he was called "The American Bad Ass." He beat Test at SummerSlam, and then jumped to Smackdown. He received a title shot against Brock Lesnar at Unforgiven, but the match ended indecisively. The rematch was in Hell in a Cell at No Mercy, and Undertaker lost. A few days later, the Big Show came to Smackdown and challenged Brock to a title match. Undertaker confronted him, but was then thrown off the stage by the Big Show and was put out of action.