Reagan v Carter
The California cowboy had the reputation as a non-intellectual, an actor no less, and it played him in good stead against Carter's comparative intellectual mien and effete-ism.
Reagan v Mondale
Mondale, with his soft patrician sweaters and "low energy" vibe, couldn't appeal to Joe Lunchbox, nor sometimes even to the faculty lounge lizard.
Bush v Dukakis
True, George HW Bush was the ultimate patrician white male, but he came off as more corny than intellectual in his speech ("Not gonna do it!", "Read my lips!") and he was facing an opponent who looked the part of a patrician and whose picture is under the dictionary captioned: "Pointy-headed Massachusetts intellectual."
Clinton v Bush
Clinton masked his policy wonk streak with an Arkansas background, down home speech, and the reddest of redneck families. The ultimate non-patrician white male.
Clinton v Dole
The bland Midwestern politician Dole looked like a Founding Father, and was, in fact, a contemporary of the Founding Fathers. Way too much of the Senate parliamentarian/patrician.
W. Bush v Gore
W. Bush was the anti-intellectual cowboy riding in to save the day from Gore, who was even whiter than Bush and heavily into non-blue collar fetishes like climate change and paying advisers on how to become more of an "alpha" male. That doesn't play in Ohio biker bars.
W. Bush v Kerry
It's a little known fact that John Kerry played a philatelist in the film "How I Married Into Money". He also got an honorable mention under the dictionary definition of "Pointy-headed Massachusetts intellectual".
Obama v McCain
Obama, although a cerebral type, betrays none of that in his speeches, which tend to be "folksy" and littered with brainless slogans like "Hope and Change!" and "Yes We Can!". McCain, while no intellectual, has enough of a patrician about him given his white hair, good manners, and family background.
Obama v Romney
Romney is so stiff and W.A.S.P.-ish that the state of Massachusetts filed a formal complaint against his campaign, saying that Democrats have the patent on these guys (see Dukakis and Kerry).
Trump v Clinton
Trump is the iconic nouveau riche guy whose idea of noblesse oblige is the obligation to hit back harder than he got hit. He's also the least intellectual person you'd care to know. Hillary combined nerdy-ness and lying, a particularly poor combo.