#1 WWE legends Shawn Michaels and The Undertaker
Although the Shawn Michaels vs. The Undertaker rivalry is widely considered to be one of the greatest in WWE history, the two Superstars were never supposed to face each other in WWE.
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Bruce Prichard revealed on the That’s Gotta Be Kane! episode of WWE Untold that Vince McMahon repeatedly said in the 1990s that Michaels and The Undertaker would never go one-on-one.
In September 1997, the WWE Chairman finally had a change of heart when he decided to book Michaels vs. The Undertaker at WWE In Your House: Ground Zero, kick-starting a rivalry that went on to last for several months.
The man behind the ‘Taker character, Mark Calaway, confirmed in the WWE Untold episode that he did not get along with Michaels in those days.
“Where Shawn Michaels and I are today and where we were at back then on a personal level... it's taken a complete 360 [180]. If Shawn Michaels back then was on fire, I probably wouldn't p*** on him to put him out.”
Michaels and The Undertaker went on to work with each other at back-to-back WrestleManias at WrestleMania 25 and WrestleMania 26, with ‘Taker winning both matches.
The first match is viewed by many WWE fans as one of the best WWE matches of all time, while the second brought an end to Michaels’ legendary in-ring career.
Eight-and-a-half years later, the rivalry was revisited when Michaels came out of retirement and joined forces with Triple H to defeat Kane and The Undertaker at WWE Crown Jewel in November 2018.