#1 Bret Hart vs Kurt Angle
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If there was one man that could have ever been the top nemesis of Bret Hart, that man would the the Olympic Gold Medalist, Kurt Angle. Let's look at the contrasts:
-- Canadian hero vs American hero
-- Both amateur wrestlers
-- Competitve spirit to out-wrestle everyone
While Bret Hart retired from WCW in 2000, following a kick to the head at Starrcade 1999, Kurt Angle won his first WWE Championship at No Mercy 2000 against The Rock. The timing for a Bret Hart vs Kurt Angle clash was never aligned due to The Hitman's concussion in 1999 and stroke in 2002. However, if the Excellence of Execution had not received his 2002 stroke, we could have maybe seen the dream match at WrestleMania XX.
Though the dream match never came to fruition, there are many possibilities of how this match could have gone if they had faced each other in their prime. For instance, Bret Hart's 1997 heel persona against Kurt Angle's 2003 babyface persona could have provided great psychology and given the fans a program that gathered more attention than just being a classic, all-out wrestling match.