#6 Bret Hart
The Hitman. The best there was, the best there is, and the best there ever will be. Or, at least that’s what he and his family members like to tell people. This one really couldn’t happen unless Bret Hart stayed with the WWF instead of jumping ship to WCW, for the same reason that it couldn’t easily work with Hulk Hogan. But that’s in hindsight, with a 21-year streak to protect. In reality, The Undertaker was very close to facing Bret Hart at WrestleMania, but instead ended up working a program with Diesel. Hart and ‘Taker faced off the Royal Rumble PPV instead.
Not to stretch outside the realm of possibility here, but if you could mix and match the two from the prime of their careers, you’d obviously take Bret from his early ’90s run as WWF Champion, and mix him up with late 2000s Undertaker prior to his matches with Shawn Michaels. But if that’s the case, there’s a nearly infinite number of possibilities…
#5 Chris Jericho
Chris Jericho and the Undertaker in any era would have been a great match, but if I’m fantasy booking, I think the target year is 2009. Yes, that means we wouldn’t have had the first Undertaker vs. Shawn Michaels classic, but there’s always the 2010 sequel, and I don’t doubt Jericho at the peak of his character could have filed that role perfectly, if not better.
In 2008 Jericho threw Shawn Michaels through the JeriTron 6000 and pronounced that “Y2J” was dead. In its stead, he created a stone cold serious persona based off Javier Bardem’s character in No Country for Old Men. His subsequent run was the best of his career. Jericho ended up facing Roddy Piper, Ricky Steamboat and Jimmy Snuka in a handicap match at WrestleMania XXV, after talks with actor Micky Rourke fell through. It wasn’t bad, and Steamboat definitely brought a surprising amount of fight to the match, but it also didn’t steal the show.
I’m not saying it’d be worth scrapping the first Michaels/Undertaker match, but as Jericho is one of my favorite performers ever, it might be worth considering to have both dream matches satisfied…
