America’s first third-party presidential candidate ran under the banner of the Anti-Masonic Party, a political faction born out of the belief that the Freemasons were a murderous secret society that sought to impose their will on the electorate. In 1832, the Anti-Masons stepped onto the national stage by nominating former U.S. attorney general William Wirt to oppose incumbent and Freemason Andrew Jackson in the presidential election.

There was just one problem—Wirt was himself an ex-Freemason, and he admitted in his acceptance letter that he considered the group a harmless “social and charitable club” with no conspiratorial aims. He even tried to drop out of the race after concluding that his presence was likely to split the anti-Jackson vote and give the president an easy victory. Party leaders persuaded Wirt to soldier on until Election Day, but the reluctant candidate only won 100,000 votes and carried a lone state—Vermont.

Perhaps best known for her 1872 run for the presidency of the United States as the first woman to do so, Victoria Woodhull spent her lifetime blazing trails across multiple disciplines. From an early age, it’s thought she believed that she received special guidance and protection from the spirits of the deceased, which empowered her to take actions unusual for a woman at the time.

In addition to her candidacy for president, Woodhull was also the first woman to own a Wall Street investment firm, found her own newspaper, and speak before Congress demanding that women be granted the right to vote. And while her run for political office didn’t end with her moving into the White House, Woodhull was elected ​​president of the American Association of Spiritualists in 1871, calling it “the chief honor” of her life.

Along with Victoria Woodhull, the challengers in the 1872 election also included New York Tribune founder Horace Greeley, a brilliant and eccentric newspaper editor known for dabbling in everything from temperance and vegetarianism to spiritualism. Greeley secured the nominations of both the Democratic Party and the offshoot Liberal Republican Party, but his attempt to unseat incumbent Ulysses S. Grant was nothing short of a disaster.

Political cartoonists such as Thomas Nast had a field day satirizing Greeley’s appearance—he sported a set of unruly whiskers and often wore a flowing white overcoat—and despite his past support for the abolition of slavery, the newsman was widely criticized for championing post-Civil War reconciliation with the South. Greeley’s troubles only mounted after his wife died shortly before Grant cruised to victory on Election Day, and his own failing health later forced him to check himself into an asylum. He passed away on November 29, 1872, becoming the only presidential candidate in history to die before the Electoral College had been totaled. Greeley’s 66 electoral votes were subsequently distributed among several other Democratic candidates.

Socialist icon Eugene V. Debs ran for president five times during the early 20th century, but it was his final bid in 1920 that proved to be the most surprising. Just two years earlier, the pacifist labor leader had been charged with sedition, stripped of his citizenship and sentenced to 10 years in prison for giving a speech calling for resistance to the World War I draft. Debs received the Socialist Party nomination despite the charges, and proceeded to campaign from the Atlanta Federal Penitentiary under a variety of slogans including “From the Jailhouse to the White House.”

Though restricted to just one public statement per week, he netted over 900,000 votes in the general election, finishing a respectable third behind Republican Warren G. Harding and Democrat James M. Cox. President Harding would later commute Debs’ prison sentence and set him free in 1921, but his U.S. citizenship was not restored until 1976—50 years after his death.

In 1936, as the Nazis tightened their grip on Germany, a fringe religious mystic and Adolf Hitler acolyte named William Dudley Pelley launched an unlikely bid for the American presidency. The Massachusetts native had previously worked as a Hollywood screenwriter before a near-death experience inspired him to create “Liberation Doctrine,” a religious system that combined elements of spiritualism and New Age philosophy. He later became the subject of intense government scrutiny for founding a fascist, anti-Semitic and anti-immigrant paramilitary group called the Silver Legion of America.

Pelley made his White House run on the upstart Christian Party ticket, campaigning against Roosevelt’s New Deal and arguing that, “the time has come for an American Hitler and a pogrom.” Despite giving numerous speeches, he only succeeded in getting on the ballot in the state of Washington, where he received fewer than 2,000 votes. Pelley continued his controversial activities after the election and was later imprisoned on sedition charges for publishing pro-Nazi literature during World War II.

Gracie Allen was a comedian known for hosting a wildly popular radio show alongside her cigar-chomping husband, George Burns. During the 1940 presidential election, the couple staged a now-legendary publicity stunt by throwing Gracie’s hat in the ring as the nominee of the tongue-in-cheek “Surprise Party,” which featured a kangaroo as its mascot and the slogan “It’s in the bag.”

Allen toured the country on a whistle-stop tour, and fans flocked to hear her quips on the national debt (“we ought to be proud of it, it’s the biggest in the world!”) and her lack of a vice president (she was adamant that she would “tolerate no vice” in her administration). First Lady Eleanor Roosevelt even got in on the fun by inviting Allen to speak at the Women’s National Press Club. Allen suspended the joke campaign a few months before Election Day, but not before she was unofficially elected mayor of a small Michigan town and endorsed by Harvard University’s student body. She went on to receive a few thousand write-in votes during Franklin D. Roosevelt’s landslide victory in the general election.

Kansas-born Earl Browder ran as the Communist Party’s presidential candidate in both the 1936 and 1940 elections, and once appeared on the cover of Time Magazine as the face of American Marxism. While he never succeeded in gaining traction for his campaigns—he won fewer than 100,000 votes on both occasions—Browder has since become famous for his alleged ties to Soviet espionage in the United States. According to decrypted government cables released in the 1990s, Browder campaigned for the White House while simultaneously serving as a go-between for Soviet intelligence, and may have taken part in covert activities along with several members of his family. One study has even claimed that he personally recruited many of the Soviets’ American spies.

While Browder was never convicted of espionage during his lifetime, he was jailed for over a year for passport fraud before being pardoned in 1941. He was later expelled from the Communist Party after World War II for arguing that their philosophy could coexist with capitalism.

Dr. Benjamin Spock is best known as the author of 1946’s Common Sense Book of Baby and Child Care, which became the bible of a generation of parents during the post-World War II “baby boom.” But along with his work as a pediatrician, he was also a former Olympic gold medal-winning rower and—in 1972—a surprise candidate for president.

Spock’s political career came on the heels of several years as a Vietnam War protestor and advocate of nuclear disarmament. “It isn’t enough to bring up children happy and secure,” he once argued, “you need to provide a decent world for them.” As the nominee of the People’s Party, Spock advanced a liberal platform that called for an end to American military intervention overseas, the legalization of marijuana and free healthcare. He only succeeded in winning ballot access in 10 states, however, and finished fifth with 78,000 votes. Spock later resumed his work as a political activist and was arrested for civil disobedience more than a dozen times before his death in 1998.