#2: Should: Baron Corbin

Okay, I know I'm going to get a lot of flack for saying this, but I really like Baron Corbin.
As a heel, Corbin's ability to rile up the crowd is unparalleled, and the former boxer has the in-ring skill as well. At just 34 years old, Corbyn still has plenty of years left in his career, and defeating The Undertaker would cement his legacy as a truly phenomenal heel forever.
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It's not like Corbin hasn't already done this before, as it was the former United States Champion who toppled Kurt Angle in the Olympian's retirement match at WrestleMania 35.
Having Corbin finish the legendary Phenom would be the biggest win of the Constable's career and would follow the time-honoured tradition of having the older Superstar go out with a loss to benefit the next generation.
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