I'd say this election is most comparable to 1960

[twenty42]

Popular incumbent president. Incumbent party runs a candidate with close ties to the administration who has little in the way of their predecessor's charisma and electability.

Challenging party nominates a neophyte with more style than substance.

Results in the popular vote are extremely close and controversial, whereas the electoral college results are much clearer and more decisive.

The winners of both elections won by smartly and strategically focusing on key states, whereas the losers lost by underestimating the importance of key states and wasting precious time and resources collecting wasted votes.

[m4567]

I think think and hope it's 1976.

[Unconditional Surrender Truman]

I suppose there are certain similarities, but I still hold 1828/1832 to be a better comparison all around.

[Fusionmunster]

Except the popular vote wont be extremely close when all is said and done.

[pbrower2a]

All that Donald Trump has in common with JFK is just barely winning, and having a sex life of ... female diversity.

He';s going to be an abrasive, unimaginative, rigid, and extremist conservative. 

[White Trash]

I suppose there are certain similarities, but I still hold 1828/1832 to be a better comparison all around.

[Orser67]

Good point about 1960, it is a pretty good comparison

[m4567]

2000 was 1960.

[Sedona]

A good comparison on the Nixon/Clinton front, not so much on the Kennedy/Trump front.

[Absentee Voting Ghost of Ruin]

1928. Uncouth, prominent and wealthy businessman with an international reputation but no elective-office experience and no military background is grudgingly accepted by the GOP establishment. He wins an election aided by a divided Democratic party. The election also sees Republican control of Congress along with many state legislatures and governerships across the nation.

[Pyro]

This will either prove to be a 1968 or a 1976 election in time.

[tonyreyes89]

1828, 1980, 2000

[Blue3]

Or 2016 is the first 2016.

I know it's comforting to try and fit this year into previous patterns, but thinking this year would fit into previous patterns made just about everybody wrong about Trump from start to finish.

I know why people are trying to do this, but it's ultimately pointless in any real meaningful sense.

[LLR]

Nah, I think 1948 is better.

Trump/Truman - run populist campaign based on WCWs mostly in the midwest, comes back from behind for a surprise win.

Clinton/Dewey - "elitist" from New York, was so sure of victory that didn't try competing for swing voters, got taken by surprise.

[Beefalow and the Consumer]

1896, except this time WJB won.

[Intell]

1896, except this time WJB won.

maybe in characteristics, but Bryan would be much more similar to Clinton then to trump in terms of ideology.

[Sir Mohamed]

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.

[Devout Centrist]

1896, except this time WJB won.

[Southern Senator North Carolina Yankee]

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.

I seem to recall a situation involving Alabama's votes putting the nationwide PV vote in doubt. Basically votes were counted for Kennedy that should have gone to an indy Dem slate or something like that.

[RINO Tom]

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.

[Southern Senator North Carolina Yankee]

1896, except this time WJB won.

Intell is right, thought. In terms of style and generalized "populism", perhaps. But the simple fact of the matter is that Industrial populism is far different from agrarian populism and Trump is a Northern candidate through and through both in terms of his background as a NY Developer and also the location of the votes he brought in to make his electoral coalition a majority (rust belt North).

McKinley is if an anything a mirror image of Trump, reflecting the fact that we are now post-industrial. McKinley exemplifies how for a century the GOP would win its middle/upscale base in the North and then augment that by winning enough working class votes on ding ding ding Protectionism to sweep all the Northern states and overcome the Solid South.

Trump is inverse in the sense that he utilized Trade to formulate his base among working class voters and then won just enough of the middle/upscale (what we call college educated whites) to win those states and make it work.

Another reason why Trump is the inverse of McKinley is that McKinley represented the transition from pro-business nationalist economics of the American System (Hamilton, Clay, Lincoln etc) within the GOP to the pro-Business Laissez-Faire economics the 20th century GOP that would eventually move away from protectionism entirely and embrace Free Trade wholesale ninety years later (1980). If Trump succeeds as President, he will begin the reversal of that transition and set us on a course for a Midwest centered GOP dominated by a 21st century revival of nationalist economics.

This means that Trump is also a reverse Ronald Reagan. Reagan probably provides Trump's best model for FP, but on economics/Trade/Immigration, Trump is undoing the Reagan Revolution as far as the GOP is concerned.

The Steve Bannon pick likely means that Trump is conscious of this potential transformation of the Republican Party and his presence, increases its likelihood substantially. Democrats are wise to be up in arms over this, because this transformation would dictate a likewise realignment of the Democratic Party in a direction many on the left will find uncomfortable. 

[Sir Mohamed]

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.

I seem to recall a situation involving Alabama's votes putting the nationwide PV vote in doubt. Basically votes were counted for Kennedy that should have gone to an indy Dem slate or something like that.

Btw, the comparison of the running mates also fits well: Dick “the warmonger” Cheney is somewhat comparable to Pence, who also stated that W’s VP is his role model. Both were mainly picked due to their congressional experience, that the nominee lacked. Lieberman and Kaine are also comparable: Both centrist Democrats and more of the “calm, nice guy” sort.

[TheElectoralBoobyPrize]

1928. Uncouth, prominent and wealthy businessman with an international reputation but no elective-office experience and no military background is grudgingly accepted by the GOP establishment. He wins an election aided by a divided Democratic party. The election also sees Republican control of Congress along with many state legislatures and governerships across the nation.

You forgot both winners are protectionists. Also, the Democrats nominated a "first" in each case...first Catholic, first woman.

[Unconditional Surrender Truman]

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.

I seem to recall a situation involving Alabama's votes putting the nationwide PV vote in doubt. Basically votes were counted for Kennedy that should have gone to an indy Dem slate or something like that.

Sort of. In 1960, the Alabama Democratic Party split between Kennedy loyalists who supported the national ticket and those who favored a slate of unpledged electors who could then act as kingmakers after the election. The compromise reached was to nominate a split slate, with half the electors pledged to Kennedy and the rest remaining unpledged (these electors ultimately voted for Byrd). This makes it hard to know who won the popular vote in Alabama that year, because unlike most other states, Alabama's electors were chosen in eleven separate races: instead of voting for the Democratic slate or the Republican slate, voters had to go through and vote for eleven electors, and could divide their votes however they wanted. This raises the question of whether you count votes for the Democratic unpledged electors as votes for Kennedy or as votes for Byrd; the latter gives JFK the state (and a slim plurality in the popular vote); the latter leaves Nixon as the winner on both counts.

[Crumpets]

By extension, the 2020 election:

Mike Pence/Marco Rubio
Cornel West/Lena Dunham