Of all Undertaker's WrestleMania victims, none have fallen as far (or as heavily) as Jake Roberts. Once one of the most chilling, innovative heels in the business, his 1992 loss to the Deadman signalled the beginning of a depressing downward spiral which would sadly come to define him. The match itself came in the midst of a heated contract disagreement, with Roberts threatening to no-show the event if he was not granted his release. This stemmed from anger he felt at being refused a place on the creative team, a role he had previously been promised by Vince McMahon. The 'Mania clash was his last WWF match for four years. After a short, calamitous stint in WCW (in which he took part in the infamously poor "coal miner's glove match"), he returned to the WWF and put over Steve Austin at King of the Ring 1996 to arguably kickstart the Attitude Era. Unfortunately, after stepping away from in-ring competition, Roberts relapsed into the drug and alcohol problems that had plagued him throughout his earlier career. Had Roberts not been booked into his WrestleMania match with 'Taker, he may not have had the leverage to step away from his contract - ironically saving him from the beginning of a steep fall from which his career would never recover.
