22. Two Dark Souls – Jake Roberts – WrestleMania 8
The Undertaker’s first actual feud leading to a WrestleMania match would occur in 1992 with the legendary Jake “The Snake” Roberts. Early in the year, Roberts and The Undertaker were allies until Roberts viciously attacked the “Macho Man” Randy Savage. Undertaker would stop Roberts from attacking Savage, turning his face for the first time in his career.
This would lead to a confrontation on Paul Bearer’s Funeral Parlor where Roberts would attack The Undertaker, setting up their match at WrestleMania 8. Much like his first WrestleMania match, The Undertaker made pretty short work of Jake “The Snake” Roberts by defeating him in about six and a half minutes.
21. One To Forget – Giant Gonzalez – WrestleMania 9
The Undertaker’s match with Giant Gonzalez was significant for a few reasons, and none of them were really good. As a whole WrestleMania 9 is considered to be one of the worst in the history of the pay per view series, and this match definitely didn’t help things out. This would be the only time that the Undertaker would win via disqualification during his historic streak.
The match was basically set up due to Undertaker’s feud with manager Harvey Wippleman and Kamala. To get revenge, Wippleman introduced Giant Gonzalez, who not only looked ridiculous with painted on muscles and hair on a body suit, but he could not wrestle either. Thankfully, the match was short at around seven minutes, and Giant Gonzalez didn’t even last a year in the WWE.
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