Before the likes of Triple H and The Rock emerged as main-event players, Stone Cold Steve Austin and The Undertaker were the only legitimate draws at the disposal of the company.
Sure, Vince McMahon could be classified as a draw, especially during his feud with Austin, but he was not really a wrestler. Meanwhile, Mick Foley and Kane were good, great even, but just a step below the likes of Steve Austin and Undertaker.
In a span of a short time, Shawn Michaels was forced to retire due to his back being crushed and WWE had disgraced Bret Hart a few years prior. As soon as Austin won the title off of HBK, he was thrust into a feud with Vince McMahon and his handpicked monster, The Undertaker.
Austin And Undertaker Feuded A Few Times
While Triple H started calling himself The Game and The Rock flourished as a quick-witted jock in the upper card, Undertaker and Steve Austin were embroiled in a feud, all the way up to Judgement Day in 1998.
A couple of months later, in 1999, Austin and Undertaker again crossed horns, with the latter having grown far more demonic. At that point, Undertaker wore all black, whispered about demons and darkness, and regularly conducted sacrifices for a higher power, all on live television.
As the Lord of Darkness, Undertaker desired control of the company and began targeting Vince McMahon. This led to the boss relying on Steve Austin, his former nemesis. And as we know, Vinny Mac ended up being the revered “Higher Power” and the angle became the stuff of legends, but we were given a few more Austin and Undertaker matches throughout his chaotic saga.
On their own, Undertaker and Austin are put on an illustrious pedestal, and rightfully so, as they are two of the most popular superstars in the history of the company. That being said, despite dozens of championships and a plethora of epic matches between them, Austin and Undertaker never really had a classic, rivalry-defining match against each other.
Austin versus Rock. Hart versus Austin. Undertaker versus HBK. These are the kinds of matches that define legacies and feuds but not a single Austin and Undertaker match even comes close to the caliber of the aforementioned contests.
Not counting live events, Undertaker and Austin wrestled a total of 14 times and just a single one is remotely good. The match on the 20/01/1997 episode of RAW is WAR was the only decent contest as the feud bombed in 1998, at least in terms of in-ring work. Even the inclusion of Kane did little to help matters as the two just did not work well together.
Jim Ross, a friend to both these wrestlers, noted that despite the level of massive respect between them, Austin and Undertaker do not share in-ring chemistry, and they just do not click. Austin had tremendous chemistry with Rock while Undertaker worked extremely well with HBK but against each other, these two never put on a great match.
Even with a whole lot of hype, the matches came up short in terms of quality. The stage was set for a thrilling encounter at SummerSlam 1998 as the WWE championship was on the line but sadly, mere minutes into the match, a headbutt from The Undertaker legitimately knocked out Austin and broke his jaw. The rest of the match was a slow, plodding affair. This match was supposed to put the rivalry into perspective, but the botch marred the rest of the contest.
Moreover, the timing of the aforementioned matches is also something to consider. The encounter in 1997 was actually pretty decent, largely because Undertaker was still pretty mobile. However, by 1998, Undertaker had slowed down in the ring due to lingering injuries.
Injuries And Lack Of Chemistry Hindered In-Ring Action
By 1999, he did not even wrestle much as he was not able to work any sort of match. By the same token, Austin was never the same after he broke his neck and while he was able to have matches with ring-generals like Triple H and extremely charismatic and athletic youngsters like the Rock, Undertaker was neither of those in 1998, and he was unable to carry Austin to a match, and vice versa.
The promos and segments were great, incredible even as these two superstars were charismatic as all hell. Even the ludicrous reveal of Vince McMahon as the higher power was iconic in a way, largely because of the presence of these two superstars. More importantly, the crux of the feud was something to look forward to, as a badass antihero was up against a very evil entity.
Sadly, chemistry is inherent, and it is something that cannot be created, and these two megastars just did not have chemistry with one another.