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Shawn Michaels talks relationship with The Undertaker ahead of ‘Last Ride’

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Shawn Michaels and The Undertaker will forever be linked.

While Michaels is most often connected to Bret Hart, his work with The Undertaker represents some of the most brilliant in-ring displays in WWE history. Michaels and Taker main-evented three pay per views together during a critical five-month period for WWE that spanned from September 1997 to January ’98, which included the first-ever Hell in a Cell match.

Michaels plays a big role in this Sunday’s installment of WWE’s Last Ride documentary. Following Michaels’s return to full-time wrestling in 2002, he put together a string of unforgettable matches against talent that included Chris Jericho, Kurt Angle and Ric Flair. But his most iconic pieces of work were back-to-back masterpieces with The Undertaker at WrestleMania 25 and 26.

Michaels connected with Sports Illustrated to discuss the evolution of his friendship with The Undertaker, covering both the highlights and lowlights together in the ring as well as providing additional detail regarding their work together from the Saudi Arabia show in November 2018.

Justin Barrasso: The bond between you and The Undertaker took time to develop, especially considering there was never a particular fondness for one another early on during your time together in WWE. Why, initially, was there friction?

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