In the late 1990s, two of WWE’s most iconic superstars, The Undertaker and Shawn Michaels, were at the forefront of the wrestling world. By 1998, as the WWF was emerging victorious in the ‘Monday Night War,’ both men were undeniable forces—both in the ring and behind the scenes. However, their personal relationship was far from smooth, leading to a complex and sometimes contentious dynamic between them.
Tensions behind the scenes between Undertaker and Shawn Michaels
While both The Undertaker and Shawn Michaels were massive stars, their personalities often clashed. As the leader of the Bone Street Krew (BSK), The Undertaker had a strong presence in the locker room, enforcing discipline and maintaining order.
On the other hand, Michaels and his faction, The Kliq, often caused tension within the locker room with their rebellious attitudes. This created friction between the two men, with The Undertaker frequently frustrated by Michaels’ behavior.
Undertaker and Shawn Michaels: magic in the ring
Despite their backstage struggles, when The Undertaker and Michaels faced off in the ring, something special happened. Their 1997 Hell in a Cell match is still regarded as one of the greatest bouts in wrestling history.
Their chemistry was undeniable, as they pushed each other to deliver a match that became a defining moment of both their careers. Their unique connection in the ring overshadowed any personal grievances, showcasing their unmatched ability to perform.
The Undertaker speaks out
In a candid interview on Busted Open Radio, The Undertaker opened up about his feelings towards Michaels during those early years. He admitted that, despite Michaels being a brilliant performer, he had little regard for him as a person.
"If I was to go backstage and see Shawn Michaels on fire, I wouldn’t p*ss on him to put him out," he confessed. However, The Deadman also recognized Michaels’ in-ring talent, praising him for his ability to have incredible matches with anyone.
A reconciled friendship
When Michaels made his return to WWE in 2002, the two began to mend their relationship. Over time, they developed a strong friendship. Recently, both The Undertaker and Michaels teamed up to announce Triple H as the headliner for the Hall of Fame class of 2025, showcasing the bond they’ve built over the years.