Say what you will about our country’s electoral process: presidential candidates know how to bring the drama. On this week’s episode of Join or Die with Craig Ferguson, HISTORY’s late-night host and his celebrity panelists will discuss just some of the (many) White House hopefuls who never stood a chance—but ran unforgettable, and sometimes cringeworthy, campaigns regardless. Read on for more about some of America’s most doomed presidential candidates ever.

7. CHARLES COATSWORTH PINCKNEY, 1804

Thomas Jefferson’s first term came on the heels of a close (and bitter) race. Four years later, he earned his second in an absolute blowout. Of the 17 states that participated in the 1804 election, Jefferson lost only Connecticut and Delaware. Those two holdouts gave his opponent, Federalist Charles C. Pinckney, a combined 14 electoral votes. Jefferson got 160.

6. GEORGE CLINTON, 1808

Following a tradition established by George Washington, Thomas Jefferson chose to step down from the presidency rather than seek a third term. So, on January 23, 1808, 89 leaders of his Democratic-Republican party got together in the Senate chambers to pick a nominee for the 1808 campaign.

Before long, a clear frontrunner emerged. Secretary of State James Madison received some 83 votes, while the remaining six were split between James Monroe and Vice President George Clinton. Unsurprisingly, Madison took home the nomination. Clinton decided to run for president anyway (also as a Democratic-Republican). Alas, the bold move didn’t pay off and Clinton was trounced in the general election. Still, he did get a nice consolation prize—under President Madison, the native New Yorker was able to resume his duties as VP before dying in office on April 20, 1812.

5. JOHN BELL, 1860

There was only one core issue defining the Constitutional Union Party: if elected president, their pick would remain aggressively neutral on the slavery issue. In 1860, America looked poised to tear itself apart over this toxic subject. Only by ignoring it could a Civil War be avoided—or, at least, so thought the CUP.

Founded in 1859, the party held its first (and only) national convention during the summer of 1860. A former Whig senator, Bell was chosen as their presidential nominee. With Edward Everett—another ex-senator—as his running mate, he did surprisingly well, claiming the electoral votes of Tennessee, Kentucky, and Virginia. Not bad, but not nearly enough.

4. GEORGE MCCLELLAN, 1864

In politics, momentum can shift in a flash. As the summer of 1864 drew to a close, Abraham Lincoln’s chances for a second term looked grim. With the war going badly, even the president’s longtime allies deemed his defeat inevitable. That August, Republican strategist Thurlow Weed (who’d helped organize Abe’s 1860 campaign) grimly told a colleague, “Lincoln is gone, I suppose you know as well as I.”

Across the aisle, the Democrats were divided into two factions: those who insisted on seeing the war through and the pro-peace “copperheads” who demanded an immediate end to hostilities by any means necessary. After much discussion, the party selected military man George McClellan—one of Lincoln’s former generals—as its nominee. It was agreed that he’d run a pro-peace campaign.

Unfortunately for the Dems, party members fighting for the Union assumed the pacifist stance was a commitment to accepting peace at any cost—a position that felt disloyal after the sacrifices they had made in the fight to reunite the country. Soldiers that might have otherwise supported the Democratic nominee threw their support behind Lincoln.

Not helping matters: On September 6, 1864, Union General William T. Sherman captured Atlanta, thus all but guaranteeing a northern victory in the war. Just like that, McClellan’s fate was sealed—Lincoln triumphed 212 to 21 in the electoral college.

3. RUFUS KING, 1816

King was the last of a dying breed. The Federalist party to which he belonged hadn’t won a presidential race since John Adams bested Thomas Jefferson in 1796. Increasingly, their candidates were seen as elitist and out of touch. The Federalists’ reaction to the War of 1812 only solidified this assessment.

Denouncing this conflict as an expensive waste of human life, New England Federalists threw an anti-war convention in Hartford, Connecticut. Beginning on December 15, 1814, the event raged on into January. Their timing couldn’t have been worse. While the Federalists debated, General Andrew Jackson scored a moralizing victory at the Battle of New Orleans. Shortly thereafter, a peace treaty was signed.

This fortuitous turn of events made those who’d attended the Hartford Convention seem hopelessly detached and even unpatriotic. Now less popular than ever, the Federalist party faded away into oblivion. King would be their final presidential candidate. In the electoral college, Democratic-Republican James Monroe easily crushed him with 183 votes to King’s 34. When Monroe sought re-election four years later, he more or less ran unopposed.

2. STEVEN A. DOUGLAS, 1860

This Midwestern Democrat planted the seeds of his own downfall. Douglas was the main architect of the controversial Kansas-Nebraska Act, which sparked a tidal wave of violence between pro- and anti-slavery settlers out in the Kansas territory in 1854.

Throughout the act’s ratification debate, Douglas vocally supported the ideal of “popular sovereignty.” This concept held that new territories should be permitted to decide for themselves if they’d allow slavery within their borders. Southern Democrats didn’t care for the idea, fearing that it could threaten the rights of slave owners. So began a major-league rift. In 1860, the Democratic party threw two separate conventions—northern delegates nominated Douglas as their presidential candidate while their southern brethren backed John C. Breckenridge of Kentucky.

Ultimately, both Democrats ended up running against each other—as well as John Bell of the short-lived Constitutional Union Party, and Republican Abraham Lincoln. His foes divided, Honest Abe emerged victorious—even though 60 percent of the electorate picked somebody else.

1. MARTIN VAN BUREN, 1840

When the economy gets rough, voters tend to punish whoever’s sitting in the Oval Office. Just ask Van Buren. Less than a year into his first term, America entered the biggest recession it had ever seen. Nearly 800 national banks folded during the so-called “panic of 1837,” while the country’s unemployment rate skyrocketed.

Most historians hold Andrew Jackson—Van Buren’s predecessor—responsible for setting up the catastrophe. From the start, “Old Hickory” hated the powerful Bank of the United States. In 1832, he dealt it a mortal blow by withdrawing all federal funds from the organization. Altogether, these holdings added up to roughly $10 million, which Jackson deposited in various state and private banks. With the old BUS destroyed, land speculation spun wildly out of control. Before long, this bubble burst and when the new banks started calling in loans, they found that many borrowers simply couldn’t pay up.

By and large, Van Buren kept supporting Jackson’s failed economic policies. On his watch, the recession only worsened. It didn’t help, of course, that amid all this turmoil, Van Buren had developed a reputation for lavish spending. In 1840, President Van Buren was ousted, with William Henry Harrison (a Virginia Whig) defeating him by the hefty margin of 174 electoral votes.

Catch a new Join or Die with Craig Ferguson this Thursday at 11/10c on HISTORY. Disagree with our ranking? Click here to see a different take on hopeless presidential campaigns.