@Scott, I would love to hear how a McCarthyist stoner who looks like Rust Cohle from "True Detective" somehow managed to be elected president in 1960!
IT WAS THE SIXTIES MAAAAAN.
Another poster (I think Razze?) included Allen Ginsberg in one of his hypotheticals, so it only made sense to include his better, less problematic half. Vietnam still happens but Kerouac's election paves a quicker path forward for social liberalism in America, eventually giving way for the election of the first openly-LGBT black female president in 1980 (following nearly three years of the first Mormon president, no less!). The Silent Majority eventually says enough is enough and the Christian Right holds power for sixteen uninterrupted years. Another realignment gets anti-Christian icon Marilyn Manson elected in a very narrow three-way race, before he is easily defeated after the 2008 crash. Following that, America goes back to electing social moderates as the religious culture wars lose steam.
Or, at least that's how it played out in my head.