The Heartbreak Kid Shawn Michaels vs. The Undertaker (Aug 1997 – Oct 1997)

Background

The Undertaker came into the summer of 1997 as WWF Champion, having beaten Sycho Sid at WrestleMania 13 on March 23 with an assist from Bret Hart, who delivered the interference that let Undertaker land a clean Tombstone.[3] It was his second reign, and through the spring he defended it while a mystery built underneath him: Paul Bearer, the manager Undertaker had rejected, kept threatening to reveal Undertaker's darkest secret unless he was taken back.[2] Undertaker vs. Sid had been locked in as the WrestleMania 13 main event even before Shawn Michaels gave up the title, the Observer reported.[19] On June 30, Bearer made good on the threat, telling the world that Undertaker had started the 1967 fire at the family funeral home that killed their parents, and that Undertaker's brother Kane, long presumed dead in that fire, had survived and was coming for him.[2] Undertaker spent the following weeks publicly discrediting the story without ever fully denying it.

Shawn Michaels, meanwhile, was rebuilding a career he had walked away from months earlier. On February 13, 1997, on a Thursday Raw Thursday in Lowell, Massachusetts, the night he was scheduled to defend against Sid, he told the crowd a doctor had said he might never wrestle again because of his knee, delivered the "I've lost my smile" promo, and surrendered the WWF Championship to WWF President Gorilla Monsoon.[17][16] Bret Hart never believed the injury was as bad as advertised, and said so for years afterward: "Shawn had a doctor's note that said he shouldn't wrestle. But in our business, you wrestle hurt all the time. Shawn just didn't want to drop the belt to me," Hart said, adding that he had watched Michaels doing backflips backstage without a limp shortly before the diagnosis came down.[16] Whatever the truth, Michaels was back in a WWF ring by May, sporting a more arrogant character and escalating his on-air needling of Hart.[16]

At SummerSlam, Michaels was put in the middle as special guest referee for the WWF Championship match between Undertaker and Bret Hart.[17] The stipulation carried real stakes for everyone in the ring. Hart could never wrestle in the United States again if he lost, and Michaels would face the same fate if he showed obvious bias toward either man.[3] Nobody involved intended for Michaels himself to become the story.

Build-up

SummerSlam took place on August 3, 1997, at the Continental Airlines Arena in East Rutherford, New Jersey, in front of 20,213 fans.[3] Late in the match, Michaels confronted Hart about a chair Hart had brought into the ring, Hart spat in his face, and Michaels swung the chair and hit The Undertaker with it instead.[17][5] A dazed Michaels reluctantly counted three, and Hart won the WWF Championship at 28:08.[17][5] Michaels insisted afterward that the shot had been a genuine accident.

The Undertaker was not interested in that explanation, and neither, it turned out, was Michaels' own behavior in the weeks that followed. On the August 11 Raw in Biloxi, Michaels pinned Mankind after Rick Rude, making a surprise return after seven years away, hit Mankind with a chair behind the referee's back. Triple H and Chyna had come to ringside partway through.[17] The next week Rude opened Raw saying he'd been paid well for his work and would provide "insurance" for anyone who paid up.[17] The four of them were the nucleus of the group that would soon call itself D-Generation X. That same August 18 Raw in Atlantic City, Undertaker and Mankind beat Michaels and Triple H by disqualification at 12:18, when Michaels hit Undertaker twice in the head with a steel chair and busted him open. Undertaker sat right up, and the heels cleared out.[17] This time there was no spit and no ducking opponent to blame it on. Reporting on the rivalry has since pointed to that second chair shot as the moment that undercut Michaels' insistence that SummerSlam had been unintentional.[5]

Ground Zero: In Your House on September 7 in Louisville gave Michaels and Undertaker their first one-on-one match in the promotion, and it never settled anything. Before the match officially started, Undertaker attacked the referee who got between him and Michaels, and chased Michaels around ringside for several minutes until a replacement referee came out.[17] It ended in a no contest at 16:02, after each man had beaten up a referee and Triple H and Chyna had interfered for Michaels. Afterward a crowd of wrestlers held the two apart until Undertaker dove over the top rope onto Michaels and a pile of heels.[17]

Thirteen days later, at WWF One Night Only in Birmingham, England, Michaels turned his attention to a title of his own, with Triple H, Chyna, and Rick Rude working the outside to help him take the WWF European Championship from The British Bulldog. Bulldog hurt his ankle on the floor, and the referee stopped the match at 22:53 with him in a figure-four, while Bulldog's wife, mother, and sister, who was being treated for cancer, watched from ringside.[17] It was a numbers game rather than a clean win, and it left Michaels walking into the Undertaker rematch as a titleholder himself, flanked by the same three allies who would shortly be barred from ringside entirely.

Bearer's Kane story kept running underneath all of it. Undertaker kept denying the specifics in interviews and promos through September even as he stopped short of calling the fire story an outright lie, and the buildup to Badd Blood folded both threads together: the Michaels rematch would decide a WWF Championship challenger for Survivor Series, and it would happen inside a structure built, by Undertaker's own later account, entirely to give Kane a debut nobody could interfere with. "The whole thing was designed for Kane's debut," Undertaker said years afterward on Steve Austin's Broken Skull Sessions. "You're gonna keep all outside interference out, and boom, here comes Kane."[6] With D-Generation X banned from ringside inside a locked cage, the September chaos had nowhere left to go but up and over the top of it.

The Matches

Badd Blood: In Your House ran October 5, 1997, at the Kiel Center in St. Louis, drawing 21,151 fans, a sellout and a new attendance record for the building, and a reported 240,000 buys, a 0.60 buyrate.[1][17] The afternoon carried a real tragedy underneath the show: Brian Pillman, scheduled to face Dude Love that night, was found dead in his hotel room, and his death was announced during the Free for All preshow before the card went on.[4][17]

Triple H, Chyna, and Rick Rude walked Michaels to the ring and went back to the locker room once the cage door was locked.[17] Officials checked under the ring before the bell to rule out interference.[12] The Undertaker destroyed Michaels in the early going, with Michaels bumping all over the ring and having no answer for him.[13] Michaels cut him off by knocking him off the apron, followed with a tope suicida, and climbed the cage wall for an elbow drop. He then piledrove Undertaker onto the ring steps, a spot that sounded like it had cracked Undertaker's skull.[13] Michaels was busted open along the way, and his blood dripped onto the camera equipment.[12]

Midway through, the cell door had to be unlocked to get an injured cameraman, a local independent wrestler, to safety, and the two men brawled out through it.[17] Michaels climbed the structure to escape, and Undertaker followed him to the roof, where he hit him with a back body drop and a press slam while Michaels bled down onto the camera below. Michaels then went off the side of the cell through a ringside commentary table, after climbing part of the way down first.[13]

Back in the ring, Undertaker hit Michaels with a chair and a chokeslam, and then the arena lights went out.[13] Kane's silhouette appeared, and he tore the cell door off its hinges to get inside, prompting Jim Ross's call of "That's gotta be Kane!!" as the crowd realized what they were watching.[2] Kane delivered a Tombstone Piledriver to his own brother and left, and Michaels crawled over to make the cover at 29:56.[17][2] Dave Meltzer rated the match five stars in the Wrestling Observer, and the Pro Wrestling Torch named it its 1997 Match of the Year.[1][15][17] The Observer's and Pro Wrestling Illustrated's 1997 Match of the Year awards went instead to Bret Hart vs. Steve Austin at WrestleMania 13.[17]

Aftermath

The win did exactly what it was designed to do: it put Michaels in the WWF Championship match against Bret Hart at Survivor Series on November 9 in Montreal, the match that ended with Vince McMahon ordering the bell rung on Hart's own Sharpshooter without a submission, the finish remembered as the Montreal Screwjob.[11] Everything Badd Blood built toward Michaels emptied directly into that night five weeks later.

The next night's Raw in Kansas City set up both halves. Kane made his first television appearance by interrupting a Hardy Boyz match, chokeslamming both brothers at once and throwing them to the floor, while Paul Bearer promised that Kane would destroy everyone in his path until he got to Undertaker.[17] On the same show, Bret Hart called Michaels and Triple H "degenerates." At the next week's taping, Michaels answered by calling his group D-Generation X for the first time.[17]

Undertaker's half of the story moved slower. He refused for weeks to retaliate against Kane, telling the character he would not fight his own flesh and blood no matter how much Kane attacked and embarrassed him in the interim.[7] That restraint broke at the January 18, 1998 Royal Rumble. Undertaker had Michaels in the casket after a jumping Tombstone when Triple H knocked out the referee and a wave of heels ran in. Kane came out, cleared the ring, and then chokeslammed Undertaker into the casket himself, and Michaels shut the lid to retain the title at 20:35.[18][7] The two brothers finally wrestled each other at WrestleMania XIV on March 29, 1998, where it took three Tombstone Piledrivers for Undertaker to put Kane away, at 16:58.[18][7]

The Michaels-Undertaker relationship itself had one more beat left before the year was fully closed out. After the chaos of Montreal, Michaels went looking for Undertaker to see where the promotion's other cornerstone star stood on what had just happened. Undertaker met with Vince McMahon, then found Michaels and told him simply, "We're cool," before walking off.[14] Michaels later called the two of them "two pillars in the WWE that everything was built around," different as people but bound by what the company needed from both of them at once.[14]

Behind the Scenes

Michaels and Undertaker have both said for years that their in-ring chemistry never extended past the curtain, at least not in 1997. "I think in some ways, when we were younger, we were frustrated because we had so much unbelievable natural chemistry in the ring with each other, and had zero of it outside the ring," Michaels said later. "At the time, I was an extremely difficult person. He was less so."[8] "There was clearly never any real trouble between the two of us. We just did not care for one another because we were so different," Michaels said.[10]

That gap showed up even in how they approached the biggest match of their careers to that point. Michaels has recalled that the plan called for something like thirty to thirty-five minutes, but backstage before the bell, agent Bruce Prichard told them they actually had fifty-five minutes of television time to fill. "I looked at Mark, and asked him what we were going to do with 55 minutes left," Michaels said. Undertaker's answer, in Michaels' telling, was to shrug it off: "I'll walk slow."[8]

The roof spot was Michaels' idea, and he had to talk the office into it. "I knew right away when I saw [the Cell] that, 'My God, I gotta get on top,'" he said. "And they would tell me no, because [staying in the ring] is what this whole thing is for. So once we got them convinced to let us up there, Pat Patterson worked with us. Then it was a question of how we were supposed to get down. Because it would look silly crawling down." The answer was the announce table.[8]

Kane's debut inside that match came from a deliberate piece of design rather than an accident of booking. "The whole thing was designed for Kane's debut," Undertaker said. "You're gonna keep all outside interference out, and boom, here comes Kane."[6] For Glenn Jacobs, who had already cycled through gimmicks like Unabomb, the Christmas Creature, and evil dentist Isaac Yankem before this, the moment landed as validation rather than just another costume change. "It was probably the first time I felt like I belonged there," Kane said, crediting Undertaker's performance that night with making the debut mean something to the crowd; the two men, by their own account, barely discussed the spot beforehand and didn't feel they needed to.[7]

The trust The Undertaker withheld from Michaels in 1997 didn't fully return for months. Five months after Badd Blood, on the night of WrestleMania XIV, Undertaker positioned himself near the entrance while Michaels defended the WWF Championship against Steve Austin, having taped his own hands beforehand in case Michaels tried to avoid doing business. "I had taped my hands up," Undertaker said later. "If Shawn had not done business, there would have been an appearance by the Undertaker that night."[9] Jim Ross has told the same story from his own vantage point, saying Undertaker stood "stoically by the gorilla position" throughout the match, treating the championship as something that needed protecting regardless of Michaels' state of mind that year.[10] When Michaels eventually asked Undertaker years later whether the story was true, Undertaker lied to spare him. "I totally lied through my teeth to him because I felt bad," Undertaker admitted, though he later confirmed the substance of it: that night, he was going to do what needed to be done.[9]

Legacy

The Hell in a Cell match at Badd Blood got five stars from Dave Meltzer and was the Pro Wrestling Torch's Match of the Year.[1][15][17] It came in the middle of a year when the same handful of men carried the company: Undertaker had won the title at WrestleMania 13, Hart had taken it from him at SummerSlam with Michaels as referee, and Michaels would take it from Hart in Montreal.[17]

Kane's debut paid off months of Paul Bearer's threats inside a structure that, by Undertaker's account, was created specifically to keep outside interference out.[6] Hell in a Cell itself outlived the storyline that introduced it, becoming an annual gimmick match and eventually a branded pay-per-view of its own.

Michaels and Undertaker's personal distance in 1997 didn't last forever either. By the time both men were the promotion's elder statesmen in the late 2000s, their matches at WrestleMania XXV and XXVI were built on a real friendship that had grown out of the wary professional respect first established across that summer and fall.[11] The Undertaker went on to build the WrestleMania winning streak that defined the rest of his career; Michaels dropped the title to Steve Austin at WrestleMania XIV, his last match for more than four years;[18] and Kane, debuting as a mystery designed to last a single angle, spent the next two decades as one of the company's most enduring characters.

See Also

Sources & Further Listening

1. Badd Blood: In Your House — Wikipedia. https://en.wikipedia.org/wiki/Badd_Blood:_In_Your_House
2. Kane (wrestler) — Wikipedia. https://en.wikipedia.org/wiki/Kane_(wrestler)
3. SummerSlam (1997) — Wikipedia. https://en.wikipedia.org/wiki/SummerSlam_(1997)
4. Brian Pillman — Wikipedia (death date and Badd Blood preshow announcement). https://en.wikipedia.org/wiki/Brian_Pillman
5. "The Shawn Michaels & The Undertaker Rivalry, Explained" — TheSportster. https://www.thesportster.com/wrestling/shawn-michaels-vs-undertaker-feud/
6. "The Undertaker Reveals The Real Reason WWE Created Hell In A Cell" — TheSportster. https://www.thesportster.com/news/undertaker-hell-cell-created-kane/
7. "The Undertaker & Kane Discuss The Latter's WWE Debut At Inaugural Badd Blood" — Wrestling Inc. https://www.wrestlinginc.com/1664491/undertaker-kane-discuss-wwe-debut-inaugural-badd-blood/
8. "Shawn Michaels reflects on his iconic WWE moments with The Undertaker" — ESPN. https://www.espn.com/wwe/story/_/id/29206653/shawn-michaels-reflects-iconic-wwe-moments-undertaker
9. "The Undertaker Lied To Shawn Michaels About Taping His Fists At WrestleMania 14" — Fightful. https://www.fightful.com/wrestling/undertaker-lied-shawn-michaels-about-taping-his-fists-wrestlemania-14/
10. "Jim Ross Recalls Undertaker Ensuring Shawn Michaels Was 'Going To Do Business' At WrestleMania 14" — Wrestling Inc. https://www.wrestlinginc.com/news/2020/10/jim-ross-recalls-undertaker-ensuring-shawn-michaels-was-675471/
11. "The Secret History of Shawn Michaels and Undertaker's Rivalry" — Pro Wrestling Stories. https://prowrestlingstories.com/pro-wrestling-stories/shawn-michaels-undertaker/
12. "25 Years of Hell: Shawn Michaels vs. The Undertaker (Hell in a Cell)" — Voices of Wrestling. https://www.voicesofwrestling.com/2022/09/29/25-years-of-hell-shawn-michaels-vs-the-undertaker-hell-in-a-cell/
13. "Mike Reviews WWF In Your House 18: Badd Blood" — Scott's Blog of Doom. https://www.blogofdoom.com/2025/10/24/mike-reviews-wwf-iyh-18-badd-blood/
14. "Shawn Michaels Recalls Backstage Meeting With The Undertaker After Montreal Screwjob" — Slam Wrestling. https://slamwrestling.net/news/shawn-michaels-recalls-backstage-meeting-with-the-undertaker-after-montreal-screwjob/
15. "Every Undertaker Vs. Shawn Michaels WWE Match" — TheSportster (match ratings). https://www.thesportster.com/wwe-every-undertaker-vs-shawn-michaels-match-reviewed/
16. "The Lost Smile: The Complete History Of Shawn Michaels Vacating The WWF Championship In 1997" — Wrestling News. https://wrestlingnews.co/wwe-news/lost-smile-complete-history-shawn-michaels-vacating-wwf-championship-1997/
17. WWF 1997 results (TV tapings, house shows, and pay-per-views) — The History of WWE. http://www.thehistoryofwwe.com/97.htm
18. WWF 1998 results — The History of WWE. http://www.thehistoryofwwe.com/98.htm
19. Wrestling Observer Newsletter, March 10, 1997 (WrestleMania 13 card) — issue recap, "Wrestling Observer Flashback–03.10.97," Scott's Blog of Doom. https://www.blogofdoom.com/2025/06/17/wrestling-observer-flashback-03-10-97/

Further Listening

• Something to Wrestle with Bruce Prichard — the 1997 episodes covering Badd Blood, D-Generation X's formation, and the run-up to Montreal
• Six Feet Under with The Undertaker — Shawn Michaels' guest episode on their rivalry, chemistry, and later friendship
• Grilling JR with Jim Ross — Jim Ross's account of The Undertaker's backstage vigilance at WrestleMania XIV