Stephanie McMahon and the Undertaker crossed paths quite a few times during the Attitude Era. The Billion Dollar Princess and the Deadman were involved in some of the most chaotic and outright ridiculous storylines.

Stephanie congratulates Undertaker ahead of Survivor Series

With the Undertaker’s thirtieth anniversary coming up at this year’s Survivor Series, Stephanie paid tribute to the Deadman in a heartfelt tweet. She congratulated him on the huge achievement and said, “It’s been an absolute honor and a privilege getting to share time and memories with the Undertaker in and out of the ring over the last 30 years.”

Undertaker made his WWE debut at Survivor Series 1990. He was part of Ted DiBiase’s Million Dollar Team. He walked out with his first manager Brother Love aka Bruce Prichard.

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Standing at nearly seven foot tall, and weighing almost three hundred pounds, he looked like the scariest man to walk the face of the Earth.

While WrestleMania might be the Undertaker’s playground, Survivor Series has featured some of his most iconic moments, from his debut to his first WWE Championship win to his incredible return in 2005 and finally his 25th anniversary in 2015. That was Taker’s final appearance at Survivor Series until he returns at this Sunday’s PPV.

Undertaker’s issues with the McMahon family

Undertaker has had his issues with the McMahon family in the past. The Deadman has faced both Vince and Shane numerous times during his career. The most infamous of clashes against both McMahons came at Great American Bash in 2003 against Vince, and WrestleMania 32 against Shane.

However, Taker has the most bizarre history with Stephanie McMahon. Even though her husband Triple H was one of the Undertaker’s biggest rivals, Stephanie and Taker had a few brief run-ins during the Attitude Era.

During his Ministry of Darkness phase, Undertaker kidnapped Stephanie and tried to marry her. Stone Cold Steve Austin foiled Taker’s plot to make Steph his unholy bride. The Deadman once again crossed paths with Taker in 2003, when she became the General Manager of SmackDown.

Attitude Era was enjoyed so greatly because of such senseless incidents and hijinks. Two decades after the Attitude Era, Undertaker is still dazzling fans in WWE. However, he announced his retirement in June 2020.