2. Paul Bearer
With the possible exception of Kane, no one in WWE has spent as much time standing alongside The Undertaker than his longest tenured manager, Paul Bearer. Bearer’s career began long before his association with The Dead Man, as he was able to make quite a name for himself in Southern territories as the Bobby Heenan inspired Percy Pringle III.
Pringle’s career didn’t take off until he was paired with The Undertaker and relied on his real life training as a funeral home director in order to create one of the most endearing and hands down the most ghastly relationship in WWE.
Only the best manager-client relationships extend to real life, and it is on this philosophy Bearer and Taker’s union became one of the most successful in company history. Bearer managed Undertaker to multiple WWE World Championships, and even when the two weren’t working together, Bearer was almost always connected to Undertaker in one way or another, typically by way of a feud. Whether friends or foes, Undertaker and Bearer were always together onscreen and off, up to and including Undertaker’s tribute to his fallen friend after Bearer passed in 2013.
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