Election where you would have had the hardest time deciding who to vote for

[Unconditional Surrender Truman]

The elections of 1836 and 1840, in the sense that I'm honestly not sure which candidate was the lesser evil. Martin Van Buren was a party hack and pawn of the slave power, while William Henry Harrison was an faux-populist aristocrat whose tenure as Governor of the Indiana Territory was a horrifying combination of anti-democratic obstruction and genocidal bloodlust. As a Hoosier, I'm inclined to hate Harrison slightly more, but d*mn were they terrible.

Honorable mentions go to 1796 (ideologically, I'm closer to the Jeffersonians than to the Federalists; but I very much respect John Adams' personal integrity, and Jefferson's blindness to the excesses of the French Revolution were – to say the least – troubling) and 1880 (I would have voted for Garfield, but Hancock was the best Democratic nominee of the pre-Bryan era by leaps and bounds).