There was a four way race between Steven Douglas (Democrat), John Bell (Constitutional Union), John C. Breckenridge (Southern Democrat), and Abraham Lincoln (Republican) in 1860. It didn't go so well...

The election of 1860 certainly qualifies. The four candidates:

• Republican: Abraham Lincoln. The Republican party was entering its second presidential election. There were many competing factions within the party, from hardcore abolitionists (mostly from New England) to former Whigs to a smattering of Know-Nothings (nativists, generally anti-immigration and anti-Catholic). William H. Seward was perhaps the favorite coming into the convention, but some thought him too radical - party leaders recognized that they needed to attract moderates to have a chance. There were other candidates, but in the end Lincoln won out.

• Democrat: Stephen Douglas. The Democrats in 1860 were a deeply divided party. While they shared much of the same platform, northern and southern factions didn't agree on the contentious subject of popular sovereignty (the right of a state to choose whether slavery should be allowed). Douglas was the most popular northern Democratic candidate, but he had backed popular sovereignty after the Dred Scott court decision and during his famous debates with Lincoln in 1858. When it came time for the Democratic convention, southern Democrats wouldn't support him. When the convention voted to not include a federal slave code in its platform, southern delegates walked out and Douglas was nominated.

• Southern Democrats: John C. Breckenridge. Made up mostly of delegates who had walked out of the Democratic convention. Breckenridge was Vice President under James Buchanan. He was a slaveowner, but not as virulently pro-slavery as many of his colleagues.

• Constitutional Union: John Bell. The Constitutional Union party was formed when it became clear that a Republican victory might mean secession. It attempted to avoid the slavery issue altogether, pledging "to recognize no political principle other than the Constitution of the country, the Union of the states, and the Enforcement of the Laws. This was enough to win a few border states where the Democratic vote was split by Douglas and Breckenridge.

Obviously, Lincoln won, due in large part to the fact that Democratic votes were split between Breckenridge and Douglas, and Bell didn't have any significant northern support.