I'd say this election is most comparable to 1960

[Beefalow and the Consumer]

1896, except this time WJB won.

Are we seriously saying that Hillary Clinton was as conservative as McKinley or that Trump was anywhere near as liberal as WJB?!  Jesus, not everything is an urban/rural divide, haha.

Trump won by bringing labor interests into his coalition, focusing on a divisive policy that favored economic elites (for Trump, global free trade, for WJB, the gold standard).  Trump didn't win because of the urban/rural divide. Trump won by gaining in small, northern urban pockets like the Fox Valley, WI; Saginaw, MI; Dayton, OH; Scranton-Wilkes-Barre, PA.  Also in industrial suburbs like Warren, MI and Lorain County, OH (Kerry won this Trump county by over 12 points!) .

[zorkpolitics]

The analogy of 2000 is much better than 1960. The JFK/Trump comparison does not fit very well. The only things they have in common is their interest in lots of women and the status of a billionaire. Thus JFK won the PV, though very narrowly.

Well its not clear Kennedy won the popular vote. 
He is credited with all 318,303 democratic votes in Alabama, but his name was not on the ballot.  Only Democratic Electors were listed and 6 of the 11 electors selected were on the States Right slate and voted for the States Rights candidate Strom Thurmond.  So he really should only be credited with 5/11 of the Alabama vote or 144,683, in which case he lost the popular vote by 60,793