To a large extent, the WWF was carried through the mid-90s on the shoulders of three men: Bret Hart, Shawn Michaels, and the Undertaker. While Bret's interactions with both Shawn and Undertaker have been covered in great depth elsewhere (and therefore won't be here), Shawn and Undertaker just never seemed to cross paths for some reason.
That all changed at Summerslam 97, when Shawn was booked to referee the WWF Title match between Undertaker and Bret. While Shawn's involvement was an offshoot of his feud with Bret, it ended up diverting him into a feud with the Undertaker. Bret goaded Shawn into swinging a chair at him, but Bret moved and Shawn creamed the Undertaker instead. Bret made a cover and Shawn, who would be contractually banned from the WWF if he showed any bias against Bret, had no choice but to make the three count and hand his worst enemy the WWF Title.
The focus after Summerslam was not on Bret tricking Shawn, but rather on Shawn costing Undertaker the title, causing a somewhat abrupt heel turn by Shawn after he turned on the fans for judging him. Shawn soon formed the original Degeneration X with Triple H, Chyna, and Rick Rude, and signed to main event the Ground Zero PPV against the Undertaker. That match ended in a disqualification, so to ensure that Shawn would be forced to face the Undertaker without being able to rely on DQs or outside interference, their rematch a month later at Badd Blood became the first ever Hell In A Cell match.
The Cell was certainly a sight to behold in that it was the first time ever that the WWF, which had long used the somewhat cartoonish bright blue cage with easily climbable bars, instead had a cage made of standard metal fencing that was big enough to cover not only the ring, but the entire ringside area as well. This meant that Shawn and Undertaker would be able to fight out on the floor and use the cage or any other weapons they found without penalty, and it would truly be a showdown that only one man would walk away from.
On top of all that, the winner would go on to challenge Bret Hart for the WWF Title at Survivor Series in Montreal, and while Shawn and Bret had been itching to get their hands on each other in an offical match all year (with the match being scheduled to happen several times before plans were changed), the Undertaker wanted to close his year in grand fashion by vanquishing both Shawn and Bret en route to regaining the WWF Title he had stolen from him.
I've said many times that there isn't a human being on the planet who can sell a beating like Shawn Michaels, and this match may be one of the best examples of that talent. Though he got in bits of offense here and there, much of the match saw the Undertaker handing Shawn the beating of his life, ramming him face first into the cage, beating him up on the floor, and even taking the beating outside the cage when Shawn beat up a cameraman so WWF officials would have to open the cage to help him, and thereby allow Shawn's escape.
Shawn did one of the greatest bladejobs in history once outside, zipping the blade across his forehead in midair as Undertaker catapulted him into the side of the cage, then they fought their way up on top of the cage before Shawn tried climbing down the side and was kicked off the cage and through a ringside table. Though Mick Foley would top that fall the following year, it was still a hellacious bump and Shawn was DEAD after taking it. He tried crawling to safety inside the cage (as insane as that sounds), but Undertaker followed him in and knocked him out with a chairshot to the skull as Shawn had done to him at Summerslam.
The win and a rematch with Bret seemed within the Undertaker's reach when the lights went out, then came back in an eerie red tint as Paul Bearer revealed Undertaker's brother Kane for the very first time. Kane calmly walked down to ringside, tore the cage door off its hinges, then went inside and came face-to-face with the Undertaker. Undertaker was stunned to see the brother he had thought long dead, but Kane didn't hesitate to pick him up and Tombstone him in the middle of the ring before walking off with Bearer.
A bloody and beaten Shawn slowly stirred and dragged himself across the mat, leaving a trail of blood behind him to drape an arm across Undertaker's chest and get the win. Shawn had won the match, but had taken one of the worst beatings of his life and was almost completely lifeless as Triple H and Chyna pulled him out of the ring and literally carried him to the back. This match was easily my pick for the 1997 Match of the Year, and may have even been in the running for Match of the Decade.
Shawn went on to beat Bret for the WWF Title at Survivor Series in a match that was not the slightest bit interesting, then found himself back in the ring with the Undertaker at the Royal Rumble. The title was on the line this time around in a Casket Match that wasn't quite as good as Hell In A Cell, but was memorable for a very unfortunate reason: this was the match that put Shawn on the shelf for nearly half a decade.
At some point during the match, Shawn took a backdrop over the top rope and was probably meant to land flat on top of the casket, but overshot and caught his lower back on the corner of the casket instead. Shawn didn't immediately realize the damage that was done and was able to finish the match after Kane again interfered on his behalf and essentially handed him the win, but when he couldn't get out of bed the next morning, it became clear that something was very wrong.
Once Shawn got checked out and understood the severity of the injury, he gutted it out and dropped the WWF Title to Steve Austin at Wrestlemania 14 as planned before disappearing to try and heal up. Once Shawn realized that he wouldn't be able to rehab the injury, he underwent surgery on his lower back and ended 1998 with the belief that his in-ring career was over.
Thankfully, he turned out to be wrong and made a grand return to the ring in 2002. Though much of the ensuing decade would have him battling the likes of Triple H, Ric Flair, and Chris Jericho, the shadow of the Undertaker always loomed in the background as we wondered if he and Shawn would ever lock horns again. They did, and we'll look at the rekindling of their feud tomorrow in Part 2!