Really don't see how you can beat "billionaire versus wife of a former president" here
Hillary had a humble middle class background and actually had to work hard to get where she got. She by no means just rode off Bill's success. She was successful in her own right without him, played a big role in his success herself, and probably could have still gone far without him. I'd say that makes her less "privileged" than Al Gore, a literal "senator's son" as in "Fortunate Son." Who himself was going up against a
president's son. And yes, both had Ivy League educations, and both of their running mates also were highly privileged. Cheney was a literal oil baron and Lieberman also had a privileged Ivy League background. Ultimately I think this means OP is right and 2000 beats out 2016, as well as 2004. (Kerry actually served in Vietnam and Edwards had a humble background.)
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