It’s hard to believe that the Undertaker has been around for 25 years. Or, rather, it’s hard to believe that Taker is still wrestling (even at his massively reduced rate) today. The man has seen a multitude of eras come and go, a plethora of stars rise and fall, and still he stands as the pillar of consistency. It’s in that spirit that WWE is celebrating Undertaker Week, in honor of the 25 years since he debuted back in 1990 (funny enough, not as “Undertaker” but as “Cain the Undertaker”), and it’s in that spirit that we take a look back at the best matches from the Phenom.
When re-watching most of these (some have been permanently embedded in memory and/or popular culture), a few trends pop up. First, Taker’s best matches are generally the results of long feuds with one opponent of the kind that don’t seem all that prevalent nowadays. These are half-year feuds with emotional and often brutal payoffs. In that same note comes the second trend: Taker really is the king of Hell in a Cell matches. Five of the top 10 (plus an honorable mention) on this list take place inside the demonic structure that Taker helped usher in all the way back in 1997. The cell plays into the darkest parts of the Undertaker character (easily the best gimmick in the history of professional wrestling), and reminds us that behind the legacy, the nostalgic returns, and the body of work, Undertaker was supposed to be a terrifying personification of evil. Also, he was a biker at some point, but we don’t focus on that too much.