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Top 50 WWF Singles Wrestlers of the 90s

Dandy

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This has been the first thread that I have looked forward to each day in quite some time; includes some boss theme music; and has taken me down memory lane of an entire decade. That is amazing for me.
 

Mr. S£im Citrus

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Yeah, some of you guys have been ridiculous. Don’t make fun of the guy’s obvious cognitive deficiencies for thinking Razor Ramon had a better run than guys who held the main title 3+ times.
Mans is making the most out of what his deity gave him. That's something to be respected.
 

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3. Shawn Michaels

ShawnMichaelsRR_crop_north.jpg



The Rockers (1990–1991)
Main article: The Rockers
On October 30, 1990, The Rockers unofficially won the WWF Tag Team Championship from The Hart Foundation (Bret Hart and Jim Neidhart), as Neidhart, half of the championship team, was in the process of negotiating his release from the company.[19] The match was taped with The Rockers winning the title, but soon after Neidhart came to an agreement with management and was rehired.[19] The championship was returned to the Hart Foundation, while the title change was never broadcast or even acknowledged on television (though The Rockers did have a successful title defense on November 3, 1990, against Power and Glory (Hercules and Paul Roma) before the title was returned to the Hart Foundation).[19] When news spread, WWF explained that the original result was void due to a collapsed turnbuckle in the ring during the bout. A buckle had indeed broken, but not to a noticeable or dangerous extent during the match.[2] The Rockers continued their partnership, eventually splitting on December 2, 1991, during an incident on Brutus Beefcake's televised Barber Shop talk show promotional segment.[21] Michaels superkicked Jannetty and threw him through a glass window on the set of Beefcake's talk show.[5][22] Jannetty returned to the WWF the following year and enjoyed moderate success before leaving the company in 1994, while Michaels became a prominent villain of the early to mid-1990s as "The Boy Toy".[21]

Two Dudes with Attitudes (1992–1995)
See also: Two Dudes with Attitudes
At the suggestion of Curt Hennig, Michaels adopted the nickname "The Heartbreak Kid".[5] Along with his new name came a new gimmick as a vain, cocky villain.[23] He was put together with mirror-carrying manager, Sensational Sherri, who according to the storyline had become infatuated with him.[21] Sherri even sang the first version of his new theme music, "Sexy Boy".[2] During that period, after Michaels had wrestled his scheduled match at live events, his departure was announced with "Shawn Michaels has left the building", alluding to the phrase "Elvis has left the building".[24]

At WrestleMania VIII, Michaels defeated Tito Santana in his first pay-per-view singles match after both men had simultaneously eliminated each other from that year's Royal Rumble.[25] Michaels subsequently became a contender to the promotion's singles titles and failed to win the WWF World Heavyweight Championship from champion Randy Savage in his first opportunity to compete for that title at British event UK Rampage, held on April 19 at the Sheffield Arena and broadcast on Sky Movies Plus[26] (the match later aired in the US on the edition of June 15 of Prime Time Wrestling).[27] Michaels was also unable to win the Intercontinental Championship from Bret Hart in the WWF's first ladder match at a Wrestling Challenge taping on July 21, which was subsequently made available on multiple Coliseum/WWE Home Video releases.[28][29] However, he won the title from The British Bulldog on Saturday Night's Main Event XXXI, which aired on November 14.[30] Shortly thereafter, he faced Hart for the WWF World Heavyweight Championship in the main event of the Survivor Series, but lost the match.[31] Originally the secondary main event, Michaels and Hart became the primary main event after The Ultimate Warrior was unable to compete and was replaced by Mr. Perfect (Curt Hennig) in the tag team match that involved Randy Savage against the team of Ric Flair and Razor Ramon.[32] During this time, Michaels and Sherri split and he engaged himself in a feud with former tag team partner Marty Jannetty.[5] Michaels lost the Intercontinental Championship to Jannetty on the May 17, 1993 episode of Raw,[30] but regained it on June 6 with the help of his debuting "bodyguard" (and off-air friend) Diesel.[2][30]

In September 1993, Michaels was suspended for testing positive for steroid – a charge he never admitted.[33] On WWF programs, his suspension was explained by his having neglected to defend the title often enough. After turning down World Championship Wrestling (WCW)'s advances, Michaels returned to the WWF and made several appearances in the United States Wrestling Association (USWA) during a WWF/USWA cross-promotion. He returned to WWF television in November at the Survivor Series substituting for Jerry Lawler, who was dealing with legal issues, in a match pitting himself and three of Lawler's "Knights" against the Hart brothers, Bret, Bruce, Keith and Owen.[34]

In 1994, Michaels entered a rivalry with Razor Ramon, who had won the Intercontinental Championship, which had been vacated during Michaels's absence.[35] Since Michaels had never been defeated in the ring for the title, he claimed to be the rightful champion and even carried around his old title belt.[35] This feud culminated in a ladder match between the two at WrestleMania X.[35] Michaels lost the match, which featured both his and Ramon's championship belts suspended above a ladder in the ring.[34][35] This match was voted by fans as "Match of the Year" by Pro Wrestling Illustrated.[5] It also received a five-star rating from Wrestling Observer Newsletter editor Dave Meltzer, the first of nine WWF/E matches to do so. Over the next few months, Michaels battled various injuries and launched the Heartbreak Hotel television talk show segment, mainly shown on Superstars.[36]

On August 28, Michaels and Diesel captured the WWF Tag Team Championship from The Headshrinkers (Samu and Fatu).[37] The next day at SummerSlam, Diesel lost the Intercontinental Championship to Ramon when Michaels accidentally superkicked Diesel.[34] This triggered a split between Michaels and Diesel, a storyline that was drawn out until Survivor Series that November.[38] Michaels went on to win the Royal Rumble in 1995,[39] which set up a championship grudge match at WrestleMania XI against Diesel (who had gone on to win the WWF World Heavyweight Championship from Bob Backlund).[39] As part of the storyline, Michaels recruited Sid as his bodyguard for the build-up, lost the match[40] and was attacked by Sid the following night.[41] After this, Michaels took time off[41] because Vince McMahon wanted Michaels to become a fan favorite.[42]

Formation of the Kliq (1995–1996)
Main article: The Kliq
Michaels returned to the ring as a fan favorite in May 1995 and he went on to defeat Jeff Jarrett to win his third Intercontinental Championship in July at In Your House 2: The Lumberjacks.[5][43] This led to a title defense against Razor Ramon at SummerSlam in a ladder match, which Michaels won.[5] Around this time, Michaels became the leader of a backstage group known as The Kliq.[5] Critics perceive the group to have sufficient clout with WWF owner Vince McMahon, becoming dominant wrestling figures in the WWF for several years in the mid-1990s, causing friction with other wrestlers. Michaels disputes the perception, saying that McMahon pushed only deserving wrestlers.[44] Michaels's fan base was later nicknamed "The Kliq" as an inside reference to the real "Kliq".[45] In October 1995, Michaels was the victim of a legit assault outside a bar in Syracuse, New York.[2] Due to not being able to compete, Michaels was forced to forfeit the Intercontinental Championship to his original opponent Dean Douglas at In Your House: Great White North,[46] who in turn Douglas lost the championship to Razor Ramon, another member of the Kliq.[47] This event has been cited as an example of the Kliq holding others down. During a match with Owen Hart on a November episode of Raw, Hart performed an enzuigiri that struck the back of Michaels's head.[48] They continued the match, but Michaels collapsed in the ring, supposedly because he had suffered a concussion.[2][48] The concussion was scripted, which was kept from most fans at the time.[2] A retirement angle was written so that Michaels could take some time off after he came back from an injury too soon.[2]

WWF Champion (1996–1998)
Main article: D-Generation X
After teasing a retirement, Michaels returned to the WWF at the Royal Rumble match in 1996, which he wound up winning for the second year in a row, to receive a WWF World Heavyweight Championship match in the main event at WrestleMania XII.[49] Around this time, Jose Lothario became Michaels's on-screen manager.[50] At WrestleMania XII, Michaels defeated WWF Champion Bret Hart in the overtime of their sixty-minute Iron Man match, which had ended in a scoreless tie.[5] On May 19, Michaels and his fellow Kliq members were involved in the incident known as "Curtain Call". Diesel and Razor Ramon were about to leave WWF to company rival WCW. After Michaels won a match against Diesel, Ramon and Hunter Hearst Helmsley came to the ring and joined Michaels and Diesel in a group-hug.[51] As Diesel and Helmsley were seen as villains at the time, in contrast to Michaels and Ramon, this constituted a breach of "kayfabe", as acting out of character, which was rare and controversial at the time.[51] As WCW gained momentum due to the signings of Hall and Nash, Michaels held the championship for most of the year. Michaels's championship reign ended at the Survivor Series event, where he lost to Sycho Sid, his former bodyguard.[52] Michaels recaptured the championship from Sid in January 1997 at the Royal Rumble.[53]

On a special episode of Raw dubbed Thursday Raw Thursday, Michaels vacated the WWF World Heavyweight Championship.[2] He explained to fans that he was informed by doctors that he had conjured a knee injury and that he had to retire.[54] His speech was regarded as controversial, as Michaels was allegedly unwilling to lose to Bret Hart at WrestleMania 13 (since it was noted that he was going to have a rematch with Hart at WrestleMania).[5] Michaels contemplated thoughts of retirement and stated that he "had to find his smile again", which he had "lost" somewhere down the line.[5] After knee surgery by Dr. James Andrews, Michaels returned a few months later, briefly teaming with Stone Cold Steve Austin to win the WWF Tag Team Championship.[55] In his autobiography, Michaels reveals about his real-life feud with Bret Hart, claiming that Hart did interviews on live television claiming that he [Michaels] was faking his whole injury.[56]

By the spring of 1997, the real-life backstage conflict between Michaels and Hart was reaching its height. Both men were going out on television and frequently making personal, true to heart remarks about one another. Michaels briefly left the WWF in June of that year after a real backstage fight with Hart, just hours before a Raw Is War show, which allegedly resulted from Michaels making an on-air remark, known as the "Sunny Days" comment, implying that Hart (who was married at the time) was having an affair with Tammy Sytch, a manager and valet who was signed to the WWF as Sunny. Michaels and Austin were still WWF Tag Team Champions at the time during an ongoing feud with the Hart Foundation and a tournament was made to decide new tag team champions. Michaels eventually returned that summer in July. At SummerSlam, Michaels officiated the WWF World Heavyweight Championship match between WWF Champion The Undertaker and Bret Hart.[57] The match ended controversially, with Michaels hitting Undertaker with a chair (unintentionally, as he was aiming for Hart after he spat in his face).[57] Michaels was then forced to award the championship to his nemesis, Bret Hart.[57] The next night on Raw Is War, signs of a heel turn started to show as Michaels told the WWF fans what happened at SummerSlam was an accident and that he dealt with the Undertaker when the time came. At WWF One Night Only, held in Birmingham, England in September, Michaels defeated The British Bulldog to capture the European Championship.[57][58] The fans at the event were so appalled at the result of the match they booed Michaels out of the building to the extent that they littered the ring with garbage, cementing his second heel turn.[57][59] With this win, Michaels became the first Grand Slam Champion.[3] At In Your House: Badd Blood, Michaels defeated Undertaker in the first Hell in a Cell match, during which Michaels fell off the side of the 5-metre (15 ft) high structure through a table.[60] The match received a 5-star rating from Dave Meltzer.

In the fall, Michaels joined forces with real-life friend Hunter Hearst Helmsley (later known as Triple H), Helmsley's then real-life girlfriend Chyna, and Rick Rude to form the stable D-Generation X (DX).[61] Michaels continued his rivalry with Bret Hart and his reformed Hart Foundation, which was now a pro-Canada stable. Michaels taunted the group and Canada by engaging in acts such as blowing his nose with and humping the Canadian Flag. Michaels later claimed the flag desecration was Hart's idea.[62] Michaels's feud with the Hart Foundation culminated in a championship match at Survivor Series in November 1997 against Hart. Michaels came out of this match, dubbed by fans the "Montreal Screwjob", as the WWF World Heavyweight Champion.[63] Michaels now held both the WWF World Heavyweight and European championship at the same time. Michaels dropped the European Championship to D-Generation X member Hunter Hearst Hemsley in a farcical match.[64]

First retirement and hiatus (1998–1999)
At the 1998 Royal Rumble, in a casket match against The Undertaker, Michaels took a back body drop to the outside of the ring and hit his lower back on the casket, causing him to herniate two discs and crush one completely.[5][65] Michaels went on to win the match[5] but the injury rendered him unable to compete on the following month's No Way Out of Texas: In Your House as advertised, and forced him into retirement a night after losing the WWF World Heavyweight Championship to Stone Cold Steve Austin at WrestleMania XIV.[66]

After being away for nearly four months, Michaels made a surprise return to the WWF as a guest commentator on the July 13 episode of Raw Is War. Michaels continued to make non-wrestling appearances on WWF programming and on November 23 he replaced Sgt. Slaughter as the WWF Commissioner, a portrayed match maker and rules enforcer, eventually joining Vince McMahon's group of wrestlers called The Corporation as a villain.[67] Throughout late 1998 and early 1999, Michaels made regular television appearances on Raw, in which he scheduled matches, throwing around his authority, and sometimes even deciding the outcome of matches.[68][69][70] On the January 4, 1999 episode of Raw Is War, Michaels re-joined DX as a fan favorite, but disappeared from WWF television for a few weeks to have back surgery[71] and by the time he returned DX was on the way of dissolving within the next couple of months.

Michaels made occasional appearances as the WWF Commissioner during the spring and summer of 1999, but remained absent from television for the last few months of the decade.
 

HarleyQuinn

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Again, I'd take him over Undertaker. HBK was part of many memorable angles (heel turn on Jannetty, Owen's concussion angle, the Austin/DX stuff in Boston prior to WM and the Tyson stuff) nevermind his actual in-ring accomplishments. This to me is like ranking Ken Griffey Jr behind Frank Thomas in a 90s MLB ranking. Both are some of the best ever but c'mon man.
 

Cackling Co Pilot Kamala

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To use a '90s sports analogy, I think it's more akin to ranking John Stockton ahead of Gary Payton. Yeah, the latter was more dynamic in his prime but the former was more consistent.


And is it a still a hot take to say HBK did his best work in the '00s or is it consensus? HBK was my absolute favorite wrestler in the world from '96 to '98 but he was way, way too volatile in his prime to build a main event scene around long term. I'll take '90s Undertaker over '90s Shawn Michaels any day of the week and twice on Sunday if I'm building an all time roster.
 

snuffbox

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It probably came down to a time thing. Michaels was in a midcard tag team for all of 1990 and '91 so he loses 2 years of singles ratings that way. Off the active roster all of '99 and 3/4s of 1998. So, going by that metric, he gives up almost 3 full years to Undertaker (not counting the Dead Man's several stints on the shelf, during which he often remained on the Apter top 10 lists).

Unrelated to this list but if the tag title change had happened in '90 and if Neidhart had left, could the Anvil have become the BLACK SCORPION?
 

snuffbox

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And is it a still a hot take to say HBK did his best work in the '00s or is it consensus? HBK was my absolute favorite wrestler in the world from '96 to '98 but he was way, way too volatile in his prime to build a main event scene around long term. I'll take '90s Undertaker over '90s Shawn Michaels any day of the week and twice on Sunday if I'm building an all time roster.

It either is or should be consensus.
 

Cackling Co Pilot Kamala

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Unrelated to this list but if the tag title change had happened in '90 and if Neidhart had left, could the Anvil have become the BLACK SCORPION?
The Black Scorpion was explicitly built as someone from Sting's past. What connection did Big Jim have to The Stinger? I'm sure Ole Anderson could've come up with a dumb reason but JR and Conrad would be grousing about it some Thursday 30 years later.
 

AA484

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It probably came down to a time thing. Michaels was in a midcard tag team for all of 1990 and '91 so he loses 2 years of singles ratings that way. Off the active roster all of '99 and 3/4s of 1998. So, going by that metric, he gives up almost 3 full years to Undertaker (not counting the Dead Man's several stints on the shelf, during which he often remained on the Apter top 10 lists).

Unrelated to this list but if the tag title change had happened in '90 and if Neidhart had left, could the Anvil have become the BLACK SCORPION?

Somebody here gets it!

If this was a predictable thread it wouldn't be any fun! And wait until you see WCW because you ain't see nothin' yet!
 

AA484

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2. Bret Hart

PWI 500 Rankings:

1991: 21
1992: 5
1993: 1
1994: 1
1995: 4
1996: 16
1997: 20

Appeared 70 times in the PWI Top 10 WWF rankings with average rank of 2.19

Bret_Hart_bio.png



Early tenure and The Hart Foundation (1990–1991)
Main article: The Hart Foundation
After participating at the Royal Rumble in January 1990, The Hart Foundation defeated The Bolsheviks in 19 seconds at WrestleMania VI and began feuding with Demolition, who had just won the WWF Tag Team Championship against The Colossal Connection at WrestleMania VI. At SummerSlam in 1990, The Hart Foundation began their second, and final, WWF Tag Team Championship reign by defeating Demolition members Crush and Smash in a two out of three falls match with some help from Legion of Doom.[54][55] On October 30, the Hart Foundation lost the title to The Rockers (Marty Jannetty and Shawn Michaels), but a few days later, President Jack Tunney reversed the decision and the win was never acknowledged on television. The Hart Foundation's reign lasted until WrestleMania VII, where they lost to The Nasty Boys, after which the team split.[56]

Intercontinental Champion (1991–1992)
Hart won his first WWF Intercontinental Championship by defeating Mr. Perfect with the Sharpshooter at SummerSlam in 1991,[57][58] and subsequently won the 1991 King of the Ring tournament on September 7, 1991 at the Providence Civic Center in Providence, Rhode Island. Hart's first pay-per-view title defense occurred at This Tuesday in Texas, where he beat the undefeated Skinner.[59]

In January 1992, Hart was placed in a feud with The Mountie. This feud came about when the Mountie's manager, Jimmy Hart, threw water on Hart, and The Mountie proceeded to shock Hart with a cattle prod. On January 17, 1992, Hart dropped the Intercontinental Championship to The Mountie. Following the loss, Roddy Piper defeated Mountie with a sleeper hold two days later at the 1992 Royal Rumble,[60] and Bret later pinned Piper for his second Intercontinental Championship at WrestleMania VIII later that year,[61][62] making him the first wrestler in the WWF - and one of few wrestlers ever - to pin Piper's shoulders to the mat.[27] At a Wrestling Challenge taping on July 21, 1992, Hart defeated Shawn Michaels, with the Intercontinental Championship belt suspended above the ring, in the WWF's first ever ladder match.[63] Hart dropped the Intercontinental Championship to his brother-in-law, Davey Boy Smith, in Hart's first WWF pay-per-view main event at SummerSlam in August 1992, held before over 80,000 fans at Wembley Stadium.[64] Pro Wrestling Illustrated readers voted it the "Match of the Year",[65] and WWE named the match as the greatest in the history of SummerSlam.[66] Upon induction into the WWE Hall of Fame class of 2006, Hart cited the contest as his favourite match of his career.[67]

WWF Champion (1992–1996)
Hart won the WWF World Heavyweight Championship from Ric Flair at a Superstars taping at Saskatchewan Place in Saskatoon, Saskatchewan on October 12 of that year, in a match not originally broadcast on WWF television[68] – the match was instead made available on a series of Coliseum/WWE Home Video releases.[69] Hart dislocated one of the fingers on his left hand during the match and popped it back in himself so it would not affect the rest of the match.[27] He made his first successful title defense against Papa Shango on Saturday Night's Main Event XXXI. He would headline his first pay-per-view as champion with a successful title defense against Shawn Michaels at the 1992 Survivor Series,[70] and defeated Razor Ramon at the 1993 Royal Rumble.[71] He would also defend the title against contenders such as Papa Shango[72] and former champion Ric Flair[6] before losing the title to Yokozuna in his first WrestleMania main event at WrestleMania IX, after interference from Mr. Fuji. Fuji then challenged Hulk Hogan, who had come out to help Hart, to compete for the title; Hogan then won his fifth WWF World Heavyweight Title from Yokozuna.[73] In June, Hart won the first pay-per-view King of the Ring tournament, defeating Razor Ramon, Mr. Perfect, and Bam Bam Bigelow, thus becoming the only two-time King of the Ring.[74] According to Hart, he was scheduled to regain the WWF World Heavyweight Championship from Hulk Hogan at SummerSlam, but Hogan chose to drop the title to Yokozuna instead at King of the Ring.[75] Hart instead entered a feud with Jerry "The King" Lawler, who interrupted Hart's coronation, claimed he was the only king, attacked Hart and began a barrage against Hart and his family. The two met at SummerSlam in 1993, to determine the "Undisputed King of the World Wrestling Federation".[76] Hart originally won the match by submission, via the Sharpshooter, but as he would not let go of the hold, the decision was reversed to a Lawler victory by disqualification.[77] Hart and his younger brother, Owen Hart, would also feud with Lawler during 1993 in the United States Wrestling Association (USWA), with Lawler notably defeating Owen for Owen's USWA Unified World Heavyweight Championship.[78] Hart's feud with Lawler was named "Feud of the Year" by Wrestling Observer Newsletter, and voted "Feud of the Year" by readers of Pro Wrestling Illustrated.[79]

After months of dealing with Lawler, Hart received a WrestleMania IX rematch with WWF World Heavyweight Champion Yokozuna on the November 20 episode of WWF Superstars. When Bret appeared to have the match won, with Yokozuna locked in the sharpshooter, Owen came to ringside to congratulate his brother. The referee began questioning Owen's motives, which allowed Fuji to assault Bret. Owen then involved himself in the match, resulting in a victory for Yokozuna via disqualification. On the non-televised but now-canon November 22 episode of Monday Night Raw, Hart again challenged Yokozuna for the WWF World Heavyweight Championship, and again failed to regain the championship due to similar involvement from Owen.[citation needed] The brothers' disagreements set the wheels in motion for a family feud that would span the entirety of 1994.[80] At Survivor Series, the Harts (Bret, Owen, Bruce, and Keith) took on Shawn Michaels (a substitution for Lawler, who was facing legal troubles)[81] and his knights. The Harts won the match, with all of the brothers surviving except for Owen, the only Hart family member eliminated when he was rolled up by Michaels after inadvertently knocking Bret off the apron.[82] Bitter about his elimination, Owen blamed Bret for this and in the weeks ahead, blamed Bret for holding him back. Owen demanded a one-on-one match with Bret, which Bret refused to accept. In the storyline, Bret, along with his parents, worked over the Christmas holidays to reunite the family and to settle their rivalry. Bret was voted "WWF Superstar of the Year" 1993 by fans,[83] as well as the greatest wrestler of the year by Pro Wrestling Illustrated readers.[84]

At the Royal Rumble in January, Bret and Owen took on The Quebecers (Jacques and Pierre) for the WWF Tag Team Championship. Referee Tim White stopped the match after he considered Bret unable to continue after he sustained a kayfabe knee injury during the match. After the match, Owen berated his brother for costing him a title opportunity and attacked the injured knee, setting the feud between the two.[85] Later on, Hart managed to participate and win the 1994 Royal Rumble match amid controversy. Hart and Lex Luger were the final two participants and the two were eliminated over the top rope at the same time. Therefore, both men were named co-winners of the 1994 Royal Rumble match and received title shots at WrestleMania X.[86] Luger won the chance to face Yokozuna first, with Hart having to wrestle his brother Owen, before receiving his title shot. Hart lost his match against Owen[87] but went on to defeat Yokozuna for his second WWF World Heavyweight Championship.[88][89]

Hart continued to feud with his brother Owen while he also started feuding with Diesel. Hart's friend and former tag team partner Jim Neidhart returned to the WWF and reunited with Hart. At King of the Ring, Hart defended the WWF World Heavyweight Championship against Diesel. When Hart was winning the match, Shawn Michaels interfered on Diesel's behalf; Diesel appeared close to victory after he delivered a Jackknife Powerbomb yet before he could pin Hart, Neidhart interfered, therefore Diesel won by disqualification, but Hart retained his title. Neidhart left when Diesel and Michaels attacked Hart following the match. Neidhart's motivation was made clear when he helped Owen win the tournament that night, so that he could receive a title shot against his brother.[90] At SummerSlam, Hart successfully retained the WWF World Heavyweight Championship against Owen in a steel cage match.[91] This match received a five-star rating from Dave Meltzer of Wrestling Observer Newsletter, and the brothers' feud was voted "Feud of the Year" by readers of Pro Wrestling Illustrated.[79]

Hart eventually lost his WWF World Heavyweight Championship at Survivor Series in a submission match against Bob Backlund where the manager of either competitor (Davey Boy Smith for Hart, Owen for Backlund) would have to "throw in the towel" for the wrestler they were representing. When Hart was in Backlund's crossface chickenwing and Davey Boy was kayfabe knocked out, Owen persuaded his mother Helen to throw in the towel for Hart, giving Backlund the championship victory.[92] Bret's feud with Backlund would continue into the following year. He was voted the greatest wrestler of 1994 by Pro Wrestling Illustrated readers, winning the vote for the second straight year.[93]

Three days after Hart's title loss, Diesel defeated Backlund in eight seconds with a jackknife powerbomb to become the new WWF World Heavyweight Champion. By 1995, Hart was focusing on projects outwith the business, such as acting, and shifted to the number two face in the company, behind Diesel.[94] Hart challenged for Diesel's WWF World Heavyweight Championship at the 1995 Royal Rumble, in a match that was continually marred by outside interference and ruled a draw. Both men embraced in a display of sportsmanship after the match. In a rematch from Survivor Series, Hart defeated Bob Backlund in an "I Quit" match at WrestleMania XI.[95] Hart was critical with the match against Backlund, claiming it was "probably my worst pay-per-view match I ever had".[96] Hart would be the focal point of the first event in the In Your House pay-per-view series, competing in two matches at In Your House 1. He defeated Hakushi in the very first match of the in Your House series. Hart's acclaimed feud with Jerry Lawler was reignited at the event when Lawler defeated Hart due to Hakushi's (now Lawler's protégé) interference.[97] Hart beat Lawler in a "Kiss My Foot" match at King of the Ring, and defeated Lawler's kayfabe dentist, Isaac Yankem, by disqualification at SummerSlam 1995.[98] Their King of the Ring match ended with Hart shoving his foot into Lawler's mouth, then forcing Lawler to kiss his own foot.[99] Although Hart was victorious in their in-ring feud, Lawler remained strongly opposed to Hart as a commentator, and would routinely encourage Hart's opponents during matches; it would not be until Over the Limit, sixteen years later, that both men would finally bury the hatchet. After disposing of Lawler, Hart engaged in a three-month feud with Jean-Pierre Lafitte, who would be stealing the mirrored sunglasses from fans at ringside and his trademark leather jacket. At In Your House 3, Hart defeated Lafitte, to end the feud. Hart shifted his focus back to the WWF World Heavyweight Championship, defeating Diesel in a no disqualification match at Survivor Series to commence his third reign.[100][101]

In a rematch from their SummerSlam 1992 encounter, Hart successfully defended his title against the now heel Davey Boy Smith at In Your House 5: Seasons Beatings. He lost to The Undertaker by disqualification at the 1996 Royal Rumble when Diesel interfered, ultimately retaining the WWF World Heavyweight Championship, and defeated The Undertaker by disqualification in a rematch on the February 5 episode of Raw, again due to Diesel's interference.[102] Hart retained his title once again against Diesel in a steel cage match at In Your House 6, and defeated Hunter Hearst Helmsley, who was undefeated on Raw, on the March 4 episode of the show.[103] WWF Commissioner Rowdy Roddy Piper ruled that Hart would face Shawn Michaels, who had earned a WWF World Heavyweight Championship match at WrestleMania XII by winning the Royal Rumble,[104] in a 60-minute Iron Man match at the event. The wrestler with the most decisions during the 60 minutes would win the match and the WWF World Heavyweight Championship.

At WrestleMania, with less than a minute left on the clock and the score still 0–0, Michaels jumped from the middle rope; his legs were caught by Hart, and Hart locked in his Sharpshooter. However, Michaels did not submit in the last 30 seconds so the match ended in a tie. WWF President Gorilla Monsoon ruled that the match would continue in sudden death overtime. Michaels hit a superkick to win the championship.[105] Pro Wrestling Illustrated readers voted it the "Match of the Year";[65] in 2004, WWE fans voted the match as the greatest in the history of WrestleMania.[106] After WrestleMania, Hart went on a European tour over the next two weeks, coming out victorious against Stone Cold Steve Austin and Hunter Hearst Helmsley. The tour ended on April 22, and after this he took his hiatus from television. His final televised appearance was an interview taped while on the European tour in which he described his passion for wrestling was diminished, and stated that although there were offers from competing companies he might be finished with wrestling.[107]

That fall, Hart would indeed receive competing offers of employment from both WWF and World Championship Wrestling (WCW). WCW presented a 3-year, $9M contract offer to Hart,[108] while the World Wrestling Federation responded with an unprecedented 20-year contract. Finishing up his original WWF deal, Hart returned to action on a tour of South Africa on September 8, 1996, defeating Davey Boy Smith in Durban.[107] On October 21, Hart elected to re-sign with the World Wrestling Federation.[109] He was inducted into the Wrestling Observer Newsletter Hall of Fame Class of 1996.

Feud with Stone Cold Steve Austin (1996–1997)
Main article: Hart Foundation reunion
Over the summer, Stone Cold Steve Austin, who was fresh from winning the 1996 King of the Ring,[110] continually taunted Hart and challenged him to come back and have a match. After an eight-month hiatus from television, Hart returned and defeated Austin at Survivor Series in a match for the number one contender spot to the WWF World Heavyweight Championship.[111] Hart challenged champion Sycho Sid at the following month's In Your House 12: It's Time; Shawn Michaels, who was serving as a guest commentator at ringside, accidentally cost Hart the victory when he attempted to become involved in the match after being assaulted by Sid. The building tension between Hart and Michaels climaxed after the match when Hart assaulted Michaels. Hart's feud with Austin escalated at the Royal Rumble (1997), when Hart tossed Austin out of the ring, only for Austin (unbeknownst to the referees) to climb back into the ring and win the Rumble, while the referees were distracted by Mankind.[112] Hart quit the WWF the next night on Raw in protest. In order to deal with this controversy, a Fatal Four-Way between Austin and the participants he eliminated after re-entering the ring (Vader, The Undertaker, and Hart) was set up for In Your House 13: Final Four, with the winner becoming the number one contender. After then-champion Shawn Michaels relinquished the belt, though, the match officially became for the WWF World Heavyweight Championship. Hart defeated Austin, Vader, and The Undertaker in the Fatal Four-Way.[113][114] However, Austin made sure Hart's fourth reign was short-lived, costing him a title match against Sid the next night on Raw.[115] Hart challenged for Sid's WWF World Heavyweight Championship in a steel cage match shortly before WrestleMania 13, which saw Austin actually attempt to help Hart win, in order to make their scheduled match at WrestleMania 13 a title match. Concurrently, The Undertaker, who had a scheduled title match with Sid at WrestleMania, attempted to help Sid win. Sid ultimately retained, leading to a pure grudge match for Hart and Austin.[116] Following his loss to Sid, Hart shoved "announcer" Vince McMahon to the ground when he attempted to conduct a post-match interview, and engaged in a worked shoot, expletive-laden rant against McMahon and WWF management. This incident has been cited as one which helped lay the foundations of the WWF's Attitude Era, as well as the starting point of McMahon's on-air character, the tyrannical WWF owner "Mr. McMahon".[117]

At WrestleMania 13, Hart and Austin had their rematch in a submission match that would later get a 5-star rating from Dave Meltzer. In the end, Hart locked the Sharpshooter on a bloody Austin, who refused to give up. In fact, Austin never quit, but passed out from the blood loss and pain. Ken Shamrock, the special guest referee, awarded Hart the match, after which he continued to assault Austin, thus turning heel for the first time since 1988.[118] It was named "Match of the Year" by Wrestling Observer Newsletter and voted "Match of the Year" by Pro Wrestling Illustrated readers.[65] Later that night, Hart confronted Sycho Sid and The Undertaker prior to their match for the WWF World Heavyweight Championship; Hart insulted Undertaker and told Shawn Michaels (who was a guest commentator for the match) not to interfere. Undertaker won the match, which ended with Hart hot shotting Sid on the ropes, therefore costing him the title.

Hart challenged Rocky Maivia for the Intercontinental Championship in the main event of the March 31 episode of Raw. Rocky Maivia won by disqualification when Hart refused to release a figure-four leglock applied around the ring post. He faced Austin again in the main event of In Your House 14: Revenge of the 'Taker, to determine who would challenge the WWF World Heavyweight Champion in a title match at the following month's In Your House 15: A Cold Day in Hell. Austin had Hart locked in his own finishing move, the Sharpshooter, in the middle of the ring when The British Bulldog interfered on Hart's behalf, resulting in disqualification and giving Austin the victory and title match. They met once again in a street fight on the April 21 episode of Raw Is War, in which Austin injured Hart's ankle with a steel chair. The match was ruled a no-contest and Austin afterward continued to beat Hart while on a stretcher in the back of an ambulance.

In the ensuing weeks, Hart denounced American fans, because of their negative reaction to him in the recent weeks in contrast to his continued popularity through the rest of the world, and reunited with brother Owen and brothers-in-law Davey Boy Smith and Jim Neidhart. The family members formed a new Hart Foundation with Brian Pillman; this incarnation was an anti-American stable which was popular within Canada and Europe. As the leader of this stable, Hart routinely carried a Canadian flag to the ring and engaged in promos where he declared the superiority of his home nation; he became so despised by U.S. audiences that they would often throw debris during his ring entrances, interviews, and matches.[27] He was voted by Pro Wrestling Illustrated readers as the "Most Hated Wrestler of the Year" 1997.[119] At In Your House 16: Canadian Stampede, in Hart's home town of Calgary, the Hart Foundation defeated the team of Stone Cold Steve Austin, Ken Shamrock, Goldust, and The Legion of Doom, representing the United States, in a ten-man tag team match main event.[120] The Canada vs. U.S. rivalry escalated on the July 21 episode of Raw Is War in Halifax, Nova Scotia, where Bret, Owen, and Davey Boy Smith, representing Canada and the Hart Foundation, defeated the team of Dude Love, Austin, and The Undertaker, representing the U.S., in a Flag match.[121] The Hart Foundation's feud with Austin was named "Feud of the Year" by Wrestling Observer Newsletter and voted "Feud of the Year" by readers of Pro Wrestling Illustrated.[79] Hart vowed that if he could not defeat The Undertaker for the WWF World Heavyweight Championship at SummerSlam, he would never wrestle in the United States again. The Undertaker agreed to the match, and Hart won his fifth and last WWF World Heavyweight Championship after spitting in guest referee Shawn Michaels' face; Michaels swung a steel chair in retaliation, which accidentally struck the Undertaker. Michaels, who, as part of another pre-match stipulation, would be banned from wrestling in the United States if he did not remain impartial as referee, had no option but to count the pinfall, giving his rival Hart the victory.[122][123]

After SummerSlam, Michaels was pushed as the top heel in the company and negative fan reactions towards Hart in the United States softened somewhat, as he declared, "I'm not so much anti-American as I am just very, very pro-Canadian".[27] In real life, Hart did not like the new Attitude Era, instead preferring traditional values. This was used as part of his character, as Hart would insult the U.S. fans because of the success of the Attitude Era.[124] Hart successfully defended his title against The Patriot, with whom Hart had become involved in a feud as part of the Canada vs. U.S. storyline, at Ground Zero: In Your House,[125] avenging a loss to him on the July 28 Raw.[121] The Canada vs. U.S. feud would conclude at Badd Blood: In Your House, where Hart and Davey Boy Smith, representing Canada and The Hart Foundation, defeated The Patriot and Vader, representing the U.S., in a Flag match.[126] Erstwhile, in a rematch from SummerSlam, The Undertaker challenged Hart for the WWF World Heavyweight Championship at One Night Only; after reversing a Tombstone Piledriver attempt from Hart, The Undertaker dumped Hart on the apron when he would not let go of the ropes. As a result, Hart's neck was caught in the ropes, and The Undertaker was disqualified.[127] Hart later cited this as his favourite of all his matches with The Undertaker,[27] and his last great match in the WWF.[128]

During the Hart Foundation's feud with the Shawn Michaels-led D-Generation X (DX), DX framed the Hart Foundation in vandalizing the locker room of the African American stable, Nation of Domination with racist motifs. In retaliation, during a promo with D-Generation X, Hart called members Triple H (previously billed as "Hunter Hearst Helmsley") and Shawn Michaels "homos". Hart later apologized for his participation in the storyline and said that he had been pressured into it, saying, "I am not in any shape or form a racist. And I don't believe it is anything to kid around about. I also want to apologize for any remarks I made about gay people. It was a stupid mistake on my part".[128] Hart successfully defended his title against Nation of Domination leader, Faarooq, on the October 20 episode of Raw.[121] In his penultimate title defense, Hart wrestled Ken Shamrock to a no-contest on the October 27 episode of Raw Is War; while the referee was knocked out, Shamrock put Hart in an ankle lock; members of the Hart Foundation then attacked Shamrock until Shawn Michaels made the save for Shamrock and attacked Hart.[121]

The Montreal Screwjob and departure (1997)
Main articles: Montreal Screwjob and Hitman Hart: Wrestling with Shadows
Around this time, Hart's on-air rivalry with Vince McMahon also escalated. A heated ringside altercation between the two led many fans to dislike McMahon, who at the time was being exposed as owner of the WWF more and more frequently on-air. Although Hart had signed a 20-year contract back in 1996, the WWF was in a rough financial position by late 1997 and could no longer afford to honor the contract. Although Hart was arguably the biggest wrestler in the world during the mid-1990s,[129] McMahon also felt that the value of his character was beginning to wane,[130] and he encouraged Hart to approach the World Championship Wrestling (WCW) about a contract, hopefully one similar to their original offer. This was despite Hart's reluctance to leave the WWF and willingness to re-negotiate.[27][131] Hart subsequently signed a three-year contract with WCW. His final match with the WWF would be a title match against his real-life rival Shawn Michaels at Survivor Series in Montreal. Hart did not want to end his WWF career with a loss to Michaels in his home country particularly with the context of their nationality-fueled feud; and offered to lose, forfeit or otherwise give over the belt to Michaels in any other way that McMahon wanted. McMahon agreed to Hart's idea of forfeiting the championship the next night on Raw Is War or losing it a few weeks later.

Although Hart stated to McMahon he would not take the WWF World Heavyweight Championship with him to WCW TV and despite insistence from then-WCW President Eric Bischoff,[27] that Hart would join WCW with a "clean slate", McMahon was still concerned and paranoid; this led to him breaking his word in what eventually came to be known as the Montreal Screwjob. Even though Hart did not submit to the Sharpshooter, referee Earl Hebner called for the bell as if he had, on McMahon's orders. This resulted in Hart "losing" the title to Michaels.[132] The night ended with an irate Hart spitting in McMahon's face, destroying television equipment, and punching McMahon backstage in front of Gerald Brisco, Pat Patterson, and McMahon's son Shane. Hart also confronted Michaels backstage about the match finish. Many behind-the-scenes events leading up to the Montreal Screwjob were filmed for the documentary Hitman Hart: Wrestling with Shadows, released in 1998. WWE has described the Montreal Screwjob as "arguably the most controversial, most jarring moment in the annals of sports entertainment".[133]

Hart's likeness would continue to be featured in WWF media into 1998, including the title video of Raw (brawling in a ring within a warehouse),[134] and the WWF War Zone video game.[135]
 

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1. Undertaker

1991: Not ranked because PWI forgot him (true story!)
1992: 21
1993: 46
1994: 23
1995: 14
1996: 19
1997: 6
1998: 5
1999: 8

Appeared 98(!) times in the PWI Top 10 WWF rankings with an average of 3.95

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Debut and early feuds (1990–1991)
In October 1990, Calaway signed with the World Wrestling Federation (WWF). He made his debut as Kane the Undertaker at a taping of Superstars on November 19, 1990. Calaway made his official on-camera debut on November 22 at Survivor Series as a villainous character when he was the mystery partner of Ted DiBiase's Million Dollar Team.[31] Approximately one minute into the match, The Undertaker eliminated Koko B. Ware with his finisher, the Tombstone Piledriver. He also eliminated Dusty Rhodes before being counted out; however, his team won the match with DiBiase being the sole survivor. During the match, Calaway was referred to as The Undertaker, omitting the name 'Kane', which was dropped shortly after the event (and seven years later was given to another wrestler who eventually became Undertaker's younger brother of the same name). At the same time, The Undertaker switched managers from Brother Love to Paul Bearer – a histrionic, ghostly character, almost always seen bearing an urn, which he used to revive The Undertaker's strength whenever Undertaker fell victim to his opponents. Undertaker placed his defeated opponents (almost always jobbers) in a body bag and carried them to the back.[32] Throughout the end of 1990, The Undertaker mostly picked up squash victories against jobbers on Superstars of Wrestling and Wrestling Challenge tapings. He was a participant in the 1991 Royal Rumble match which was won by Hulk Hogan. He continued picking up victories in squash matches leading up to his first feud in the WWF with "Superfly" Jimmy Snuka.

WWF Champion (1991–1994)
He made his WrestleMania debut at WrestleMania VII on March 24, 1991, quickly defeating "Superfly" Jimmy Snuka.[33] He began his first major feud with The Ultimate Warrior when he attacked Warrior and locked him in an airtight casket on the set of Paul Bearer's Funeral Parlor interview segment. He would later lose to Warrior in the first-ever body bag challenge in WWF history. At King of the Ring 1991, Undertaker defeated Animal in a qualifying match before fighting Sid Vicious to a double disqualification in the Semi-Final, which saw both men eliminated from the King of the Ring tournament. The Undertaker defeated Hulk Hogan to win his first WWF Championship at Survivor Series with the help of Ric Flair and thus became the youngest WWF Champion in history, until having this record broken by Yokozuna in April 1993 at WrestleMania IX.[34] WWF President Jack Tunney ordered a rematch for This Tuesday in Texas six days later, where he lost the title back to Hogan.[34] However, due to the controversial endings of the two title matches between The Undertaker and Hogan, the title was vacated by Tunney. The title was awarded to Ric Flair as the winner of the 1992 Royal Rumble match.

In February 1992, The Undertaker's ally Jake "The Snake" Roberts tried to attack "Macho Man" Randy Savage's manager/wife Miss Elizabeth with a steel chair when Undertaker stopped him, becoming a fan favorite for the first time. The turn was solidified on the February 29 episode of Superstars, when Roberts confronted The Undertaker on the Funeral Parlor set over that incident (aired on Saturday Night's Main Event XXX). After demanding to know whose side The Undertaker was on and getting the reply "Not yours!", Roberts attacked both Bearer and The Undertaker, only for Undertaker to stand his ground and run Roberts off. The Undertaker defeated Roberts at WrestleMania VIII.[33] He then feuded extensively with wrestlers managed by Harvey Wippleman throughout 1992 and 1993, such as Kamala and Giant González. Also at this time, he headlined the first episode of Monday Night Raw on January 11, 1993, with a victory over Damien Demento.[citation needed] According to Calaway, working with González was "It was survival every night trying to figure out what he could do" and "took years off my career".[35] He faced González at WrestleMania IX, which is notable as Undertaker's only disqualification win at WrestleMania after the use of chloroform. His rivalry with Yokozuna culminated in a WWF Championship casket match at the Royal Rumble in January 1994. During the match, champion Yokozuna sealed The Undertaker in the casket with the assistance of several other villainous Wippleman-managed wrestlers to win the match. The Undertaker appeared from inside the casket on the video screen, representing his spirit, warning that he would return.[36] The Undertaker did not appear in the WWF for seven months after his loss to Yokozuna. In reality, he was given time off to allow a back injury to heal.[37]

The original Deadman Era (1994–1996)
During his absence, the WWF promoted his return by showing video clips of people who claimed to have seen The Undertaker. After WrestleMania X, Ted DiBiase introduced an Undertaker back to the WWF. This Undertaker, however, played by Calaway's real-life cousin, Brian Lee, was an impostor Undertaker (dubbed "The Underfaker" by fans) and led to the return of the real Undertaker in the SummerSlam main event, appearing as a new version of his Deadman persona, represented now by cool colors and replacing gray with purple. The Undertaker defeated the impostor after three Tombstone Piledrivers, and rolled him out in the casket that he'd brought to ringside.[36] At Survivor Series, The Undertaker defeated Yokozuna in a casket match rematch. Throughout most of 1995, Undertaker feuded with members of Ted DiBiase's Million Dollar Corporation. At WrestleMania XI, while The Undertaker was facing King Kong Bundy, Kama stole the urn and antagonized him by melting it into a large gold necklace.[36] In August, Undertaker defeated Kama in a casket match at SummerSlam.[36] Several weeks later, Undertaker injured his orbital bone near his eye, forcing a period of absence for surgery, until his return at Survivor Series.

The Undertaker returned in November at Survivor Series, wearing a Phantom of the Opera-like, gray upper-face mask.[36] In the main event of the Royal Rumble in January 1996, The Undertaker was unmasked in a WWF Championship match against Bret Hart, but Diesel interfered during the match, costing The Undertaker the championship.[38] A rematch for the title on the February 5 episode of Raw saw similar interference.[citation needed] At that month's In Your House: Rage in the Cage, while Diesel was facing Hart in a steel cage match, The Undertaker delivered a surprise attack, emerging from a hole he had ripped through the ring canvas and dragging Diesel with him down under, allowing Hart the victory.[38] After several weeks of more tit for tat between Diesel and The Undertaker, the feud culminated in a singles match between the two at WrestleMania XII, where Undertaker was victorious.[33]

The Undertaker's next feud started the next night on Raw, when Mankind made his debut and interfered in Undertaker's match against Justin "Hawk" Bradshaw. For the next few months, Mankind ambushed and cost The Undertaker several matches.[38] The feud intensified and they began taking their battles into crowds, backstage areas and in the boiler rooms of different arenas. Mankind cost The Undertaker the WWF Intercontinental Heavyweight Championship at In Your House 8: Beware of Dog, assisting champion Goldust to victory. 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" him with the mandible claw, giving him the win.[38] After Bearer's betrayal, The Undertaker took his rivalry with Mankind to a new level, resulting in a Buried Alive match in the main event of In Your House 11: Buried Alive, where The Undertaker won the match after a chokeslam into the open grave. However, after interference from The Executioner, as well as the help of several other wrestlers, The Undertaker was ultimately "buried alive".[38]

Lord of Darkness (1996–1998)
See also: Hell in a Cell and The Brothers of Destruction
After being buried alive, The Undertaker returned at Survivor Series again pitting him against Mankind, but with a unique stipulation; hanging 6.1 m (20 ft) 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 Undertaker's clutches.[39] It was also at this event that Undertaker had developed a more informal, casual "Deadman" incarnation than before. In this then-new form, he took on a Gothic, brash and rebelling persona (perhaps to better fit in with the then-budding, more adult-oriented Attitude Era). In this form, he proclaimed himself as "The Lord of Darkness".[citation needed] Following Survivor Series, The Undertaker briefly turned his attention to The Executioner, who had been interfering in his matches since his arrival. At In Your House 12: It's Time, The Undertaker defeated The Executioner in an Armageddon rules match.[39] He then moved on to feud with Vader, whom he faced in January 1997 at the Royal Rumble in a singles match, which Undertaker lost after Bearer interfered on behalf of his new protégé.[39] The two then clashed in the Royal Rumble match itself as they made it to the final moments of the match, but both were eliminated by Stone Cold Steve Austin, who had crept back into the match after his elimination was unseen. He faced both Vader and Austin in a four-corners elimination match for the vacant WWF Championship at In Your House 13: Final Four, but Bret Hart won.[40] However, the following month, The Undertaker managed to win the title for the second time by defeating Sycho Sid at WrestleMania 13.[41]

In May 1997, Paul Bearer attempted to rejoin The Undertaker, using the ultimatum of revealing The Undertaker's "deepest, darkest secret" to the world. Bearer accused The Undertaker of having burned down the family funeral home business when he was a child, killing his parents and ostensibly his younger half-brother as well. The Undertaker denied all this; however, Bearer claimed to have proof in the form of The Undertaker's alive and well half-brother Kane, who had survived though scarred and burned. Bearer raised Kane after the fire, having him institutionalized from the date of the fire into adulthood. Ever since the fire, Kane had been awaiting to exact vengeance on his older half-brother. In defense, Undertaker responded that Kane, a pyromaniac, had been the one to set the fire and could not have possibly even survived. Also during the period, Bearer had unintentionally admitted to Undertaker's mother having an affair with him. As a result, it was revealed to The Undertaker that Kane was his half-brother. Until that point, Undertaker spent his life (the entirety of the father's life) under the impression that Kane was fully related to him and his family. It was during this time that The Undertaker also made an appearance in Michinoku Pro Wrestling, defeating Hakushi in a singles match.[42][43]

Concurrent to the deep, dark secret storyline directed by Bearer, Undertaker began a new rivalry at SummerSlam when special guest referee Shawn Michaels accidentally hit The Undertaker with a steel chair shot meant for Bret Hart, costing Undertaker the WWF Championship.[41] After a double count-out draw during Ground Zero: In Your House, Undertaker challenged Michaels to the first Hell in a Cell match at Badd Blood: In Your House. During this match, The Undertaker's storyline half-brother Kane finally made his debut under the control of Paul Bearer, ripping off the door to the cell and giving The Undertaker a Tombstone Piledriver, Undertaker's trademark finisher, allowing Michaels to pin him.[41] As the storyline progressed through Bearer, Kane challenged The Undertaker, but Undertaker consistently refused to fight his half-brother. The Undertaker's final encounter with Michaels was in a casket match at the Royal Rumble. The week before on Raw, Kane had seemed to ally with his brother against Michaels' D-Generation X; however, at the event, Kane trapped him in the coffin, padlocking the casket lid and setting it ablaze which again gave Michaels the victory. The Undertaker, however, had disappeared when the casket lid was reopened.[44] After a two-month hiatus, The Undertaker returned and defeated Kane at WrestleMania XIV.[44] The two had a rematch, the first-ever Inferno match, one month later at Unforgiven: In Your House, which The Undertaker won by setting Kane's right arm on fire.[44]

The Undertaker's feud with Mankind was concluded afterward and they faced each other in a Hell in a Cell match at King of the Ring. During the match, The Undertaker threw Mankind off the roof of the 4.9 m (16 ft) cell onto a broadcast table below, in what was a preplanned move. He later performed a chokeslam on Mankind through the roof of the cell into the ring which legitimately knocked Mankind unconscious. Mankind also used thumbtacks in the match and was hit by a back body drop and another chokeslam onto them before Undertaker won the match with the Tombstone Piledriver.[44] At Fully Loaded: In Your House, The Undertaker and Stone Cold Steve Austin defeated Kane and Mankind to win the WWF World Tag Team Championship.[44] The Undertaker and Austin's reign as tag team champions lasted for only two weeks, as Kane and Mankind regained the titles on the August 10 episode of Raw.[citation needed] The Undertaker then became the number one contender for the renamed WWF Championship at SummerSlam, now held by Austin. Shortly before SummerSlam, however, The Undertaker revealed that he and Kane were working together as brothers. Despite this revelation, The Undertaker told Kane that he did not want him to interfere in the match with Austin and even though The Undertaker lost the match, he handed Austin his championship belt back after the match in a show of respect.[44] In September, the storyline continued and The 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 Mr. McMahon. At Breakdown: In Your House, The Undertaker and Kane were booked in a triple threat match with Austin for the WWF Championship, in which McMahon stated that the brothers were not allowed to pin each other. The Undertaker and Kane pinned Austin simultaneously after a double chokeslam, so the title was vacated by McMahon.[44] This event led to a match at Judgment Day: In Your House between The Undertaker and Kane 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 The Undertaker with, but as Kane had his back turned, both Bearer and The Undertaker hit Kane with the chair. The Undertaker went for the pin, but Austin refused to count the fall, attacked The Undertaker and counted out both of them.[44] Finally, The Undertaker became a villain the next night on Raw 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.[45]

Ministry of Darkness (1998–1999)
Main article: Ministry of Darkness
After Survivor Series, The Undertaker returned his attention to his previous feud with Austin for costing him the title at Judgment Day, 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, Mr. McMahon scheduled a Buried Alive match between The 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, raising it high into the arena.[citation needed] However, The Undertaker lost the match after Kane interfered.[46]

After building up to his second villainous run in the latter part of 1998, The Undertaker introduced an updated version of his Deadman identity by January 1999 – the dark priest who in the initial period of this persona reigned over a stable known as The Ministry of Darkness. In this form, he took on a wicked, demonic presence, much more so than ever before. He often claimed to be invoking and taking orders from a "Higher Power". Moreover, he often appeared in a hooded black robe and sat on a throne that was specially designed into his character symbol. With the help of his minions, he often performed sacrifices on select WWF wrestlers, using various incantations and magic words with intent to extract out the dark side of the wrestlers in question to recruit them into his Ministry. The completed Ministry of Darkness consisted of The Brood (Christian, Edge and Gangrel), The Acolytes (Bradshaw and Faarooq), Mideon and Viscera. Calaway himself did not wrestle for a period having undergone a hip replacement. As part of the angle, Undertaker expressed a desire to take control of the World Wrestling Federation, displacing its owner, Mr. McMahon. These ambitions culminated into a rivalry between The Ministry and The Corporation, ultimately resulting in a match between Undertaker and Corporation enforcer, Big Boss Man. The two faced off in a Hell in a Cell match at WrestleMania XV, which Undertaker won.[47] At Backlash: In Your House, Undertaker defeated Corporation member Ken Shamrock after interference from Ministry member Bradshaw.[48]

Thereafter, The Undertaker kidnapped Stephanie McMahon, forcing Mr. McMahon to enter into a reluctant alliance with his longtime nemesis Stone Cold Steve Austin. The Undertaker attempted to marry Stephanie before sacrificing her in an eldritch ceremony conducted by Paul Bearer, but Austin was able to rescue her.[49] At the Over the Edge pay-per-view, The Undertaker defeated Austin for his third WWF Championship with help from Shane McMahon, the special guest referee.[50] The Ministry eventually merged with Shane McMahon's Corporation alliance to form The Corporate Ministry. The Undertaker later revealed that Mr. McMahon had been his "Higher Power" all along.[51] After The Undertaker dropped the WWF Championship back to Austin following King of the Ring and lost to him in a First Blood match at Fully Loaded, his relationship with the McMahons dissolved and The Corporate Ministry disbanded.[citation needed]

The Undertaker then began a storyline where he teamed with Big Show in a tag team known as "The Unholy Alliance", which held the WWF World Tag Team Championship twice. After their victory at SummerSlam, The Undertaker suffered a groin tear and was seen limping in several matches. He avoided competing in wrestling matches in the following weeks, instead tyrannically ordering Big Show to fight all his battles and oblige all his many wishes. He also began to transition away to the biker character he would play in 2000. Per an interview with Kevin Nash, this was a move to allow Calaway to enter World Championship Wrestling with a non-trademarked persona. Had he entered WCW, it would have been as Mark Calaway. Although negotiations were described as close, he ultimately re-signed with the World Wrestling Federation.[citation needed]

To compensate for his lack of physical activity, Undertaker became more vocal on the mic, often making smart-aleck remarks and performing commentary. In September 1999, on SmackDown!, Mr. McMahon threatened that he would remove Undertaker from the Unforgiven main event if he refused to participate in a casket match against Triple H. Undertaker retorted that he did not care and maybe he would not be participating in anything, thus walking out of the WWF.[52] In reality, Calaway went on a hiatus from the WWF in order to treat his groin injury. He made his return to action on December 14, teaming with Viscera in a losing effort against Kane and The Godfather at a house show in Coamo, Puerto Rico.[53] The Undertaker was advertised on the Armageddon promotional poster to return, but meanwhile also tore his pectoral muscle, making him take almost eight months out of action.[54]
 

AA484

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Controversial but nobody had the staying power that he had and it was his longevity that put him at the top. He was always over, even when fighting bums in urn-stealing angles and even though he really wasn't even that strong of a promo. The only consistent guy through all 10 years of the decade, with a couple of world title reigns to boot.
 

snuffbox

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I'm surprised but not that much. For almost the entire decade, Undertaker was never below the upper midcard in the WWF. While Hart had more accomplishments and might be the GOAT wrestler, he was gone all of 98 and 99. And while the Hart Foundation was at the main event level for the first 1 1/2 years of the decade, it was still a tag team.
 

HarleyQuinn

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I can see the argument for him being #1 because despite some of the shit he suffered with; he was usually paired with somebody high up (see Yokozuna, Diesel, and HBK) or was having very memorable feuds with guys like Mankind, Kane, and others.

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