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I think they both got as far as they could go, taking into account the situations and times. Jake didn't fit the mold of Hogan, Warrior, Sid, Macho, etc... he was balding, had a pot belly and his promos were different from them, which might have made him the perfect heel for the time in actuality but it wasn't really going to happen.
As for Hall, always been a fan of his but even in WWF he was going to be the IC guy, gateway to mainevent just like Jake was. His best shot was in WCW but he ruined it for himself. To be fair though, when he was strung out the dude was damn entertaining.
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