William Jennings Bryan (1896)
Percent of the Popular Vote: 45.8
In 1896, former Nebraska Congressman William Jennings Bryan received nominations to run for president from not one, but three, parties: Democrats, Populists and Free Silver [source: Encyclopædia Britannica]. Having traveled around speaking publicly on progressive issues for the previous two years, Bryan wowed the audience at the 1896 Democratic National Convention with his famous speech, "Cross of Gold," which argued for broadening U.S. currency beyond gold. By stumping for inflated silver coinage, which would have been a financial boon to debt-strapped farmers, the nicknamed "Boy Orator" held the most appeal for rural and agrarian voters, while the Republicans' William McKinley drew in the urban electorate [source: USHistory.org].
In the end, the support of three political parties, including the Democrats, wasn't enough to whip the Republicans. Bryan gave McKinley a decent run for his money and went on to run as the Democratic nominee for president two more times, serve as Woodrow Wilson's Secretary of State and prosecute John Thomas Scopes for teaching evolution in the landmark Scopes Monkey Trial. Meanwhile, the 1896 loss also signaled the disbanding of the Populist Party.