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Undertaker
Calaway made his WWF debut as "Cain The Undertaker" at a taping of WWF Superstars on November 19, 1990. The appearance of The Undertaker's first Deadman persona was modeled after a mortician from old Western movies, wearing a trench coat and black hat with grey gloves and boot covers. Under this Deadman persona, he was "impervious to pain", something accomplished by Calaway no-selling his opponents' attacks. Calaway made his official on-camera debut on November 22 at Survivor Series as a heel when he was the mystery partner of Ted DiBiase's Million Dollar team, where he was simply called The Undertaker. Approximately one minute into the match, Undertaker eliminated Koko B. Ware with his finisher, the Tombstone Piledriver. He also eliminated Dusty Rhodes before being counted out. Shortly after Survivor Series, "Cain" was dropped from his name, and he was called simply The Undertaker. It was at this time that The Undertaker switched managers from Brother Love to Paul Bearer — a histrionic, ghostly character, almost always seen bearing an urn from which The Undertaker drew mystical power from, reviving his strength during his matches. After defeating his opponents in the ring, he would perform a post-match ritual which involved him putting his defeated opponent in a bodybag and carrying him to the back.

He made his WrestleMania debut at WrestleMania VII, quickly defeating "Superfly" Jimmy Snuka. The win was the first in his undefeated streak at the event. He began his first major feud with The Ultimate Warrior, when he attacked the Warrior and locked him in an airtight casket on the set of his manager, Paul Bearer's Funeral Parlour interview segment. After a year of battles with the Warrior, Randy Savage, Sgt. Slaughter, and Hulk Hogan, he defeated Hogan to win his first WWF Championship at Survivor Series. WWF President Jack Tunney ordered a rematch for This Tuesday in Texas six days later, where Undertaker lost the title back to Hogan.

In February 1992, Undertaker's ally Jake "The Snake" Roberts tried to attack Randy Savage's manager/wife Miss Elizabeth with a steel chair when Undertaker stopped him, becoming a fan favorite for the first time. Then, Undertaker defeated Roberts at WrestleMania VIII. He then feuded extensively with wrestlers managed by Harvey Wippleman throughout 1992 and 1993, including Kamala, whom he faced and defeated in the first televised coffin match in WWF history at Survivor Series, and Giant Gonzales, whom he defeated by disqualification at WrestleMania IX and by pinfall at SummerSlam in a "Rest in Peace" match. In January 1994, he challenged WWF Champion Yokozuna to a casket match at the Royal Rumble. At the Royal Rumble, Yokozuna sealed Undertaker in the casket with the assistance of several other villainous wrestlers, winning the match. The Undertaker's "spirit" appeared from inside the casket on the video screen, warning that he would return.

After WrestleMania X, Ted DiBiase introduced an Undertaker back to the WWF. This Undertaker, however, played by Brian Lee, was an impostor Undertaker (dubbed the "Underfaker" by fans) and led to the return of the real Undertaker at SummerSlam, appearing as a new version of his original Deadman persona, replacing grey with purple. The Undertaker defeated the impostor after three Tombstone Piledrivers. At Survivor Series, Undertaker defeated Yokozuna in a rematch, another casket match. Throughout most of 1995, The Undertaker feuded with members of Ted DiBiase's Million Dollar Corporation. At WrestleMania XI, while Undertaker was facing King Kong Bundy, Kama stole The Undertaker's urn, and antagonized him by melting it into a large gold necklace and attacking the Undertaker. Later, The Undertaker defeated Kama in a casket match at SummerSlam. Several weeks later, The Undertaker injured his orbital bone near his eye, forcing a period of absence for surgery, until his return at Survivor Series.

The Undertaker returned at the 1995 Survivor Series, wearing a Phantom-like, grey upper mask. At the Royal Rumble, The Undertaker was unmasked in a WWF Championship match against Bret Hart, when Diesel interfered in the match to cost the Undertaker the championship. One month later, at In Your House: Rage in the Cage, while Diesel was facing Hart in a steel cage match, Undertaker came bursting from under the ring, dragging Diesel underneath, allowing Hart to get the victory. This feud culminated in a match between Diesel and the Undertaker at WrestleMania XII, in which the Undertaker was victorious.

His next feud commenced the very next night, when Mankind made his debut, interfering in the Undertaker's match with Justin Hawk Bradshaw. For the next few months, Mankind ambushed and cost the Undertaker several matches. The feud intensified, and they began taking their battles into crowds, backstage areas, and in the boiler rooms of different arenas. As a result, the first ever Boiler Room Brawl was booked between the two at SummerSlam. During the match, when Undertaker reached for Paul Bearer's urn, Bearer hit him with it, betraying the Undertaker and allowing Mankind to "incapacitate" The Undertaker with the Mandible claw, giving him the win. After Bearer's betrayal, the Undertaker took his rivalry with Mankind to a new level, resulting in a Buried Alive match at In Your House: Buried Alive. Undertaker won the match after a chokeslam into the open grave, but after interference from The Executioner, as well as the help of several other superstars, The Undertaker was ultimately "Buried Alive". After being buried alive, the Undertaker returned at the Survivor Series again pitting him against Mankind, but with a unique stipulation; hanging 20 ft (6.1 m) above the ring was Paul Bearer, enclosed in a steel cage. If Undertaker won the match, he would be able to get his hands on Bearer. Even though the Undertaker won the match, interference from The Executioner enabled Bearer to escape the Undertaker's clutches. The Undertaker then briefly turned his attention to The Executioner, who had become a thorn in his side since his arrival. At In Your House: It's Time, the Undertaker defeated The Executioner in an Armageddon rules match. By the end of 1996, the Undertaker began a feud with Vader, culminating in a loss to Vader at the Royal Rumble after Bearer interfered on behalf of his new protégé. After this loss, the Undertaker began to focus his attention on the WWF Championship.

 

At WrestleMania 13, The Undertaker defeated Sycho Sid for the WWF Championship, marking his second time as WWF Champion. After the event, Paul Bearer attempted to rejoin with the Undertaker, using the threat of revealing Undertaker's "biggest secret". In the storyline, Bearer announced that Undertaker was a murderer, who as a child had burned down the family funeral home business (where Bearer worked), killing his parents and his younger half-brother. Undertaker claimed there was no way for Bearer to have that information, but Paul announced that he was told this by Undertaker's half-brother Kane, who was still alive but horribly burned and scarred. Bearer raised Kane after the fire, having him institutionalized. Now, Kane was waiting for revenge after all these years. In defense, Undertaker responded that Kane, a pyromaniac, had been the one to set the fire and could not have possibly survived.

His next major storyline began at SummerSlam in 1997 when referee Shawn Michaels was accidentally hit Undertaker with a steel chair shot meant for Bret Hart, costing the Undertaker his WWF Championship. The feud culminated at In Your House: Badd Blood, where the Undertaker challenged Michaels to the first ever Hell in a Cell match. During this match, Undertaker's storyline half-brother Kane made his debut, ripping off the door to the cell and giving Undertaker a Tombstone Piledriver, Undertaker's trademark finisher, allowing Michaels to pin him. The match would get a 5-star rating from Dave Meltzer. As the storyline progressed, Kane, with Paul Bearer, challenged the Undertaker to fights, but the Undertaker consistently refused to fight his brother. The Undertaker and Kane then formed a brief partnership when Kane saved Undertaker from an attack by D-Generation X. The Undertaker's final encounter with Michaels was in the return of the casket match at the Royal Rumble, where Kane betrayed Undertaker and cost him the win by trapping him in the coffin, padlocking the casket lid, and setting it ablaze. The Undertaker, however, had disappeared when the casket lid was reopened. After a two month hiatus, Undertaker returned and defeated Kane at WrestleMania XIV. The two had a rematch, the first ever Inferno match, one month later at Unforgiven: In Your House, where The Undertaker won by setting Kane's right arm on fire.

Undertaker's feud with Mankind was renewed afterward, and they faced each other in a Hell in a Cell match at King of the Ring. During the match, Undertaker threw Mankind off the roof of the 16 ft (4.9 m) cell onto the Spanish announce table below, in what was a preplanned move. He later chokeslammed Mankind through the roof of the cell into the ring which legitimately knocked Mankind unconscious and finished the match by Tombstone Piledriving Mankind.

At Fully Loaded, Undertaker and Stone Cold Steve Austin defeated Kane and Mankind to win the WWF Tag Team Championship. Undertaker and Austin's reign as tag champions lasted for only two weeks, as Kane and Mankind regained the titles on an episode of Raw is War. Undertaker then became the number one contender for the WWF Championship at SummerSlam, now held by Austin. Shortly before SummerSlam, however, Undertaker revealed that he and Kane were working together as brothers. Despite this revelation, Undertaker told Kane that he did not want him to interfere in the match with Austin, and even though Undertaker lost the match, he handed Austin his belt back after the match in a show of respect. In September, the storyline continued, and Undertaker began to show some villainous characteristics when he and Kane revealed the fact that they were in cahoots to rid Austin of his title for Vince McMahon. At Breakdown: In Your House, Undertaker and Kane were booked in a Triple Threat match with Austin for his WWF Championship; McMahon stated that the brothers were not allowed to pin each other. Undertaker and Kane pinned Austin simultaneously after a double chokeslam, so the title was vacated by McMahon. This event led to a match at Judgment Day: In Your House between the two brothers for the title, with Austin as the Special Guest Referee. Near the end of the match, Paul Bearer seemed about to assist Kane by handing him a steel chair to hit Undertaker with, but as Kane had his back turned, both Bearer and Undertaker hit Kane with the chair. Undertaker went for the pin, but Austin refused to count the fall, attacked the Undertaker, and counted out both brothers. Finally, Undertaker became a villain the next night on Raw is War for the first time in over six years, reconciling with Bearer and claiming that he and Bearer would unleash their Ministry of Darkness on the World Wrestling Federation. As part of this new storyline, he admitted that he had indeed set the fire that killed his parents, for which he had previously blamed Kane.

After Survivor Series, Undertaker returned his attention back to his previous feud with Austin for costing him the title at Judgment Day, viciously hitting Austin in the head with a shovel during a title match with The Rock, returning the favor for what happened a month earlier. With this twist in the storyline, McMahon scheduled a Buried Alive match between Undertaker and Austin at Rock Bottom: In Your House. In the weeks leading up to Rock Bottom, the Undertaker attempted to embalm Austin alive, tried to have Kane committed to a mental asylum, and had his druids chain Austin to his symbol and raising it high into the arena. Undertaker, however, lost the match after Kane interfered.

In January 1999, Undertaker returned and formed the Ministry of Darkness. He, however, was far more wicked than ever before, explaining that he was taking orders from a "Higher Power." He often appeared in a black robe and sat on a throne. With the help of his minions, he often performed sacrifices on various WWE superstars, which were meant to bring out the more evil side of superstars so as to recruit them into his Ministry. The Ministry eventually merged with The Corporation alliance to form the Corporate Ministry. During this time, The Undertaker was booked to defeat Austin for his third WWF Championship at Over the Edge with help from Shane McMahon, the special referee. Two weeks later, it was revealed on Raw is War that Vince McMahon had been the Undertaker's "Higher Power" all along. After Undertaker dropped the WWF Championship back to Austin one night after King of the Ring, and lost a First Blood match at Fully Loaded, his relationship with the McMahons dissolved and the Corporate Ministry disbanded.

Undertaker then began a storyline where he teamed with The Big Show in a tag team known as The UnHoly Alliance, which held the WWF Tag Team Championship twice.

the storyline leading up to WrestleMania XX, Kane was haunted by vignettes proclaiming the Undertaker's return. The first was during the Royal Rumble when Undertaker's bells tolled, distracting Kane and allowing Booker T to eliminate him. At WrestleMania XX, the Undertaker, accompanied by Paul Bearer and in his "Deadman" persona, returned and defeated Kane. Three months later, Bearer was kidnapped by the Dudley Boyz at the direction of Paul Heyman, who then took "control" of Undertaker. At The Great American Bash Undertaker fought a handicap match against the Dudleys, with the stipulation that if he lost, Heyman would bury Bearer in cement. The Undertaker won but buried Bearer anyway, explaining that Bearer was merely a liability now and that he had no use for him anymore.[41]the storyline leading up to WrestleMania XX, Kane was haunted by vignettes proclaiming the Undertaker's return. The first was during the Royal Rumble when Undertaker's bells tolled, distracting Kane and allowing Booker T to eliminate him.[39] At WrestleMania XX, the Undertaker, accompanied by Paul Bearer and in his "Deadman" persona, returned and defeated Kane.[41] Three months later, Bearer was kidnapped by the Dudley Boyz at the direction of Paul Heyman,[42] who then took "control" of Undertaker.[43] At The Great American Bash Undertaker fought a handicap match against the Dudleys, with the stipulation that if he lost, Heyman would bury Bearer in cement. The Undertaker won but buried Bearer anyway, explaining that Bearer was merely a liability now and that he had no use for him anymore.[41]

In early 2006 at the Royal Rumble, Undertaker returned during Kurt Angle's celebration of his world title defense against Mark Henry on a horse drawn cart, signaling for a title shot. As part of their storyline feud, Undertaker lost his match with Angle at No Way Out after a thirty minute bout. Undertaker cornered Angle after the match, and after a stare down, told Angle that he had his number and that he was not finished with him yet. The Undertaker had his No Way Out rematch for the World Heavyweight Championship against Angle on SmackDown! when Henry attacked Undertaker from behind, costing him the title. This began an angle between the duo, as Undertaker then challenged Henry to a Casket match at WrestleMania 22, and Henry, like Orton a year before him, vowed to end Undertaker's WrestleMania winning streak. Undertaker defeated Henry to become 14-0 at WrestleMania, keeping his storyline undefeated streak alive. During a rematch on the next edition of SmackDown!, The Great Khali made his debut and assaulted the Undertaker, signaling the end of one storyline and the beginning of a new one.

The Undertaker was not heard from until the May 5 episode of SmackDown!, as Theodore Long delivered a challenge from Undertaker to Khali for a match at Judgment Day. Undertaker lost to Khali, and he did not appear again until the July 4 edition of SmackDown!, when he accepted Khali's challenge to a Punjabi Prison match at The Great American Bash. Khali, however, was removed from the match and was replaced by ECW Champion The Big Show, over whom The Undertaker gained the victory. In the storyline, Teddy Long replaced Khali with Big Show as punishment for an attack on Undertaker shortly before the match. Khali was then challenged to a Last Man Standing match at SummerSlam after interfering in Undertaker's match with World Heavyweight Champion King Booker. Khali refused the challenge for SummerSlam, though Long made the match official for the August 18 episode of SmackDown! instead. Undertaker won the match by striking Khali with the steel stairs, delivering several chair shots, and finishing him with a chokeslam.

The Undertaker's next match was with WWE United States Champion Mr. Kennedy at No Mercy but was disqualified in the match after he hit Kennedy with the championship belt. On the November 3 edition of SmackDown!, Undertaker reunited with Kane to form the Brothers of Destruction for the first time in five years, defeating the reluctant opposition team of Mr. Kennedy and MVP, with whom Kane was feuding with at the time. As part of the storyline, Kennedy defeated Undertaker in a First Blood match at Survivor Series after interference from MVP, but finally defeated Kennedy in a Last Ride match at Armageddon. The two continued to feud into 2007 as Kennedy cost Undertaker two World Heavyweight Championship opportunities for a championship match at the Royal Rumble.

Undertaker won his first Royal Rumble match at the 2007 event,[60] becoming the first man to enter the Rumble at number 30 and win the match.[61] He then began a storyline with Batista, whom he defeated at WrestleMania 23 to win his first World Heavyweight Championship. At Backlash in a Last Man Standing match, they had a rematch that ended in a draw when neither man was able to answer the ten-count, resulting in the Undertaker retaining the Championship. On the May 11 episode of SmackDown!, Undertaker and Batista participated in a steel cage match that ended in a draw when both men's feet touched the floor at the same time. After the match, Mark Henry returned and assaulted the Undertaker. Immediately after the assault, Edge cashed in his Money in the Bank title shot, and Undertaker dropped the World Heavyweight Championship to Edge. As Undertaker laid in the ring, druids appeared and carried him to the backstage area.During Calaway's rehabilitation, Henry quickly defeated local jobbers and bragged about his assault on Undertaker, until vignettes began playing promoting Undertaker's return. The Undertaker returned at Unforgiven, successfully defeating Henry and again on SmackDown! two weeks later.[62] Batista and Undertaker reignited their feud at Cyber Sunday where the fans chose the special guest referee Stone Cold Steve Austin, but Batista retained the world title.[63] They battled again inside a Hell in a Cell at Survivor Series where Edge returned and interfered to help Batista retain the World Heavyweight Championship.[64] In response to this, Undertaker delivered a Tombstone piledriver to General Manager Vickie Guerrero, on the next SmackDown!, sending her to the hospital. Returning Assistant-General Manager Theodore Long declared a Triple Threat match for the title at Armageddon, which Edge won.At No Way Out, Undertaker defeated Batista, Finlay, The Great Khali, Montel Vontavious Porter, and Big Daddy V in an Elimination Chamber, to become the number one contender for Edge's World Heavyweight Championship at WrestleMania XXIV. He defeated Edge at WrestleMania with his "Hell's Gate" submission hold, to win his second World Heavyweight Championship and elevate his undefeated streak at WrestleMania to 16–0.[65] In a WrestleMania rematch, The Undertaker defeated Edge once again at Backlash to retain the World Heavyweight Championship.[66] Vickie Guerrero announced that the Undertaker's "Hell's Gate" was an illegal hold and stripped him of the title. The Undertaker battled Edge for the vacant title at Judgment Day, which he won by countout. Vickie ordered that the title remain vacant, because titles cannot change hands in this way. Edge and The Undertaker faced each other again for the vacant championship at One Night Stand in a Tables, Ladders, and Chairs match, which Undertaker lost after interference from La Familia. As a result of the stipulation, Undertaker was banished from WWE.On the July 25, 2008 episode of SmackDown!, Vickie Guerrero announced that Edge would face the Undertaker at SummerSlam in a Hell in a Cell match,[67] which The Undertaker won. After the match, The Undertaker chokeslammed Edge from the top of a ladder and through the ring canvas.[68] Following this match, Guerrero tried to make a peace offering with the Undertaker on SmackDown by apologizing, but the Undertaker told her that he is not the forgiving kind. At Unforgiven, as the Undertaker approached the ring to "take Guerrero's soul" and take her in a casket, the Big Show, who appeared at first to aid the Undertaker, betrayed and assaulted him.[69] As a result of this altercation, the Undertaker and Big Show faced each other in a match at No Mercy, where the Big Show knocked the Undertaker out with a punch to the back of Undertaker's head.[70] At Cyber Sunday, the Undertaker defeated the Big Show in a Last Man Standing match after applying Hell's Gate.[71] The Undertaker then went on to defeat the Big Show at Survivor Series in a casket match, to end the feud.[72]At No Way Out The Undertaker was part of the WWE Championship Elimination Chamber match, but the match Undertaker was defeated by Triple H. Undertaker has became embroiled in a long time feud with Shawn Michaels over his WrestleMania undefeated streak at WrestleMania XXV that The Undertaker never defeated Shawn Michaels in a singles match before since 1998. However, The Undertaker defeats Shawn Michaels in a first time in WWE. He has extend his WrestleMania streak to a perfect record of 17–0.[73] After WrestleMania, Undertaker took a hiatus from WWE.After four month hiatus from television, Undertaker returned at SummerSlam in August by attacking CM Punk, who had just won the World Heavyweight Championship from Jeff Hardy in a TLC match.[74] At Breaking Point, Undertaker originally won the match with his Hell's Gate submission hold in a submission match. SmackDown General Manager Theodore Long was restarted the match after stating Hell's Gate submission hold was banned by former SmackDown General Manager Vickie Guerrero that move was still in effect. Punk won the match with his Anaconda Vise when referee Scott Armstrong call the bell, despite Undertaker was never submitting (reminiscent of the Montreal Screwjob, which took place in the same venue in 1997).[75] On the September 25 episode of SmackDown, Theodore Long announced that Hell's Gate submission hold has now been officially lifted, after being released from a casket that Undertaker had apparently placed him in.[76] The feud between the two continued and at the Hell in a Cell pay-per-view, The Undertaker won the World Heavyweight Championship from Punk in a Hell in a Cell match.[77] Undertaker defend his title against CM Punk in a rematch on SmackDown. In a fatal four way match at Bragging Rights against CM Punk, Batista and Rey Mysterio. On the 16th November edition of Raw at Madison Square Garden, Undertaker teamed with John Cena against D-Generation X and the team of Chris Jericho and Big Show. After the match, Undertaker gave Cena a Tombstone Piledriver. In a triple threat match at Survivor Series against Chris Jericho and Big Show. Undertaker defeat Big Show after using Hell's Gate submission hold after Big Show knock out punch on Chris Jericho. On the 27th November edition of SmackDown, Undertaker would defend his title against Batista at WWE TLC in a chair's match. Batista originally won the match after low blow on the Undertaker when referee was distracted, SmackDown General Manager Theodore Long made a statement that low blows are illegal the match was restarted. However, Undertaker defeat Batista after using Tombstone Piledriver to retain the title.

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