10. Charles C. Pinckney
Federalist Party's nomination for president twice (first in 1804, and then again in 1808), and in both presidential elections he did terribly. In fact in the 1804 election he only got 27.2% of the popular vote and 14 electoral votes, and in the 1808 election, he only did a little bit better, getting 32.4% of the popular vote, and 47 electoral votes.
9. Rufus King
election of 1816, with only getting 30.9% of the popular vote, and 34 electoral votes. This election is also noted as basically being the death blow to the Federalist Party.
8. William H. Crawford
election of 1824 was probably the strangest presidential election in United States history, mainly because the winner had to be decided by congress (because no one won the majority of the electoral votes, which a candidate is required to win in order to become president) and all four candidates were members of the Democratic-Republican Party.
Out of all four candidates, William H. Crawford did second to worst (Henry Clay did even worse then him). Crawford only got 11.2% of the popular vote (which is worst then what Clay did), and 41 electoral votes (which is better then what Clay did).
7. William Wirt
Freemasonry was strongly opposed (especially in New England states) and actually led to the creation of a single-issue party known as the Anti-Masonic Party in 1828.
In the election of 1832 the Anti-Masonic Party fielded it's first (and only) major candidate for the presidency, William Wirt. While he did manage to win the state of Vermont and it's seven electoral votes, in the election in general he did awful, only getting 7.1% of the popular vote.
6. Hugh L. White
election on 1836 was another weird election. While the Democratic Party fielded one candidate, Martin Van Buren, the newly formed Whig Party had four candidates: William H. Harrison, Daniel Webster, Willie P. Mangum, and Hugh L. White.
Hugh L. White came in third in the election, winning only 9.7% of the popular vote, and 26 electoral votes. Of course that is better than what Webster and Mangum did, but worse then what Harrison and Van Buren did (who won that election).
5. John P. Hale
Free Soil Party was formed in 1848 to oppose the expansion of slavery within the United States, and had even fielded two major candidates in two presidential elections. The first was former president Martin Van Buren in 1848, the second was John P. Hale in 1852.
Both candidates did terribly in both elections, and in Hale's case, he only got about 4.9% of the popular vote, and no electoral votes.
4. Stephen A. Douglas
election of 1860 of another strange and complex one, fielding four major candidates, including two Democratic Party candidates.
While the main Democratic Party candidate, Stephen Douglas, with only 12 electoral votes, came in forth in terms of electoral votes (John C. Breckinridge, the other Democratic Party candidate came in second with 72 electoral votes, and John Bell, the Constitutional Union Party candidate, came in third with 39 electoral votes) he did come in second in the popular vote at 29.5%.
3. James B. Weaver
election of 1892, a new third party, most commonly known as the Populist Party, fielded a major presidential candidate, James B. Weaver.
While Weaver did manage to get 22 electoral votes, he only got 8.5% of the popular vote.
This is also the only presidential election that the Populist Party managed to get any electoral votes.
2. George B. McClellan
election of 1864, General George B. McClellan actually ran against his president and commander-and-chief, Abraham Lincoln, as the Democratic Party's candidate (it should be noted that he didn't resign from the army until the election day, November 8).
While General McClellan did win 45% of the popular vote, he only won 21 electoral votes.
1. Horace Greeley
The election of 1872 is the only election in history in which two Republicans ran for president: President Ulysses S. Grant, and Horace Greeley.
While Greenly got only 66 electoral votes and 43.8% of the popular vote, it wouldn't have mattered if he had won the election or not anyways, because he never would have become president. It wasn't that he never stood a chance of becoming president, it's that he died on November 29, 1872, before the Electoral College could even cast their votes.