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For me I perhaps view an underdog as someone perceived as "weak" but overcoming the odds to beat the establishment. So Daniel Bryan or Rey Mysterio fit that bill (not sure if the latter was in any kind of Authority-esque storyline but the fact he was small compared to a typical heavyweight champion made him an underdog).
Stone Cold I never viewed as an underdog as such as he had the physical attributes, charisma, persona to fight the establishment physically and mentally.
Daniel Bryan was always meant to come across as weak and puny and well a little pathetic at the best of times from the way he presents himself to the stupid YES movement thing etc. No characters were "scared" of Daniel Bryan whereas Stone Cold struck fear into Vince etc.
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