The Undertaker was already a two-time WWE Champion and undefeated at WrestleMania by the time The Attitude Era truly began picking up steam, but The Phenom would nevertheless continue breaking new ground throughout the late 1990s and early 2000s.
The Undertaker’s harrowing, wince-inducing Hell in a Cell Match with Mankind at King of the Ring 1998 quickly became the stuff of legend, and his sibling rivalry with Kane captivated the WWE Universe as the brothers battled in hellacious grudge matches, including the first-ever Inferno Match at WWE Unforgiven in 1998.
Not content with championship gold or other in-ring conquests, The Undertaker would make the ultimate power grab in 1999, when he formed The Ministry of Darkness and held Mr. McMahon’s daughter for ransom. The Phenom’s demand? Complete and total control of WWE. Although “Stone Cold” Steve Austin played countless mind games with The Chairman throughout The Attitude Era, The Undertaker truly hit Mr. McMahon where it hurt.
Speaking of hitting people where it hurt, The Undertaker would continue to dominate in the ring throughout The Attitude Era, with and without his Ministry. The Deadman would forge successful tandems with Big Show and even his brother, and would play an instrumental role in defending WWE from the WCW/ECW Alliance in 2001.