5) James Monroe

Presidency: 1817 – 1825 Lived: 1758 – 1831 Ranking: 14/43

Slave Owner? Yes.

His Deal: The last founding father to be president, he was rambunctious, arguing against the ratification of the Constitution, and one time being a brat to George Washington about stuff, which got him yelled at and sent to France as the new ambassador to think about what he had done.

His Presidency: Running nearly unopposed because the Federalist Party was in shambles, Monroe easily won the election and enjoyed a peaceful time while in office, cutely called “The Era of Good Feelings.” His presidency’s best-known accomplishment is the Monroe Doctrine, which states that from that point forward, if any imperialist European country tried to seize land from the United States or any other independent nation in the Western Hemisphere, the US would hit them in the face with bullets from their guns. He also bullied Spain into selling Florida to the US, which Monroe wanted because of Disney World.

Things He Can Brag About:

Having held more offices than any other president, including senator, governor, Secretary of State, Secretary of War, and the ambassador to three countries

Wanting to return American slaves to Africa, having created the nation of Liberia, and its capital being named Monrovia

Things He Hopes We Don’t Remember:

The time he released his Consul to Tunis from his post because he found out he was Jewish

The time he had a disagreement with his Treasury Secretary and acted calmly and rationally, chasing the Secretary out of the White House with a set of fire tongs

Things He’s Annoyed About:

Everyone always talking about Adams and Jefferson dying on July 4th, but he died on July 4th too and no one cares

With the opposing Federalist Party on life support, he ran unopposed in 1820 and was all excited to be the second president (after Washington) to receive 100% of the electoral votes when one dick elector voted for John Quincy Adams, who wasn’t even running

Other Notable Facts:

He was the last president to wear the hilarious Founding Fathers powdered wig. This was so 20 years ago, and it earned him the nickname “The Last Cocked Hat.”

He was broke and died with nothing

Last Words: “I regret that I should leave this world without again beholding him,” referring to James Madison. Madison commented that he was “creeped out by this.”

6) John Quincy Adams

Presidency: 1825 – 1829 Lived: 1767 – 1848 Ranking: 18/43

Slave Owner? No.

His Deal: Much like his father, John Quincy Adams was sharp, well-educated, outspoken, possibly annoying, and not really one of the cool kids. For someone who had a blah presidency, he had a great political career—excelling before his presidency as a renowned diplomat who wrote the Monroe Doctrine and after his presidency when he spent 17 years in Congress, during which he was a widely respected leader. He was best-known for his fervent anti-slavery views, and he is credited with inciting much of what became the North’s anti-slavery cause.

His Presidency: His presidency started in controversy, as he lost both the popular and the electoral vote to Andrew Jackson and only won the presidency because the margin was too narrow and it came down to a Congressional vote. This vote was deemed scandalous because Henry Clay, who surprised people by swinging favor to Adams and helping him win, was then made Adams’ Secretary of State. Adams started his presidency with lofty goals of modernizing the American economy and reforming education, and while he did get a few things done, including drastically lowering the national debt, Congress was controlled by followers of Jackson and they blocked Adams from doing most of what he wanted to do.

Things He Can Brag About:

Joining his father as the only pre-Civil War presidents to have the guts to vocally oppose slavery. Many others were morally opposed but lacked the political courage to make it part of their identity.

Being the first president to be photographed

Predicting the specifics of the Civil War decades before it happened

Being the only president who knew both the Founding Fathers and Abraham Lincoln

Having a huge role in the movie Amistad

Being great at pool

Things He’s Annoyed About:

Falling in love twice, both times having the girl vetoed by his mom Abigail, and then finally getting approved to marry a woman he considered overbearing like his mother

The time he had to do an interview naked. He and his stocky, round body enjoyed swimming nude in the freezing Potomac River every morning. One morning, a reporter stole his clothes while he was swimming and wouldn’t give them back until he did an interview. That probably couldn’t be pulled off today.

Writing the whole Monroe Doctrine as Monroe’s Secretary of State, and getting no credit for this whatsoever

Other Notable Facts:

He had a pet alligator. It lived in the White House bathtub.

He slept from midnight to 4am each night.

Last Words: “This is the last of earth. I am content.”

7) Andrew Jackson

Presidency: 1829 – 1837 Lived: 1767 – 1845 Ranking: 8/43

Slave Owner? Lots and lots.

His Deal: A tough old bastard, Andrew Jackson came from hard beginnings—his father died when he was a baby, his brother died of smallpox while they were prisoners of war together during the Revolutionary War as teenagers, and his mother died around the same time from cholera while helping to treat cholera patients. He was a notorious hothead, bordering on insane, and engaged in over 100 duels in his lifetime. As a general in the War of 1812, he earned the nickname “Old Hickory” by being “tough as old hickory” on the battlefield. His political philosophies gained a large number of followers, who for decades called themselves “Jacksonian Democrats.”

His Presidency: Jackson’s presidency was controversial, but very effective. On one hand, he was kind of a horrid White Supremacist, being a proponent of slavery and passing the Indian Removal Act, a policy that forced Native American communities westward, resulting in what’s called “The Trail of Tears” and thousands of deaths. On the other hand, he fought hard to protect popular democracy, was big on states’ rights, fought corruption, and managed to pay off the entire American debt during his term.

Things He Can Brag About:

Having his silly long face on the $20 bill

Being the founder of Memphis, Tennessee

Having Jackson, Mississippi named after him

Things He Hopes We Don’t Remember:

His conviction that the Earth was flat

Things He’s Annoyed About:

Winning the popular and electoral votes in 1824 and losing anyway

His forehead scar, which he got when he was 13, during the Revolutionary War, when he refused to clean a British soldier’s boots and the soldier slashed him

Other Notable Facts:

He was born on the border of South and North Carolina, and both states claim him as theirs (he says he was born in South Carolina).

Jackson had a lifelong cough because of a musket ball lodged permanently in his lung. Another time he was shot, he had the bullet removed without any anesthesia. Tough son of a bitch.

One of his many duels was against Charles Dickinson, who had insulted Jackson’s wife in the newspaper. Jackson let Dickinson shoot first, and he shot Jackson in the chest. Jackson just rolled his eyes and shot Dickinson and killed him.

He was the first president someone attempted to assassinate. The attempt failed, and legend has it that Jackson beat the perpetrator with his cane.

He cursed like a sailor, and as a result, so did his pet parrot. This caused a lot of problems, including the parrot having to be removed from Jackson’s funeral ceremony for cursing so much during the proceedings.

He was a red head before going gray by the start of his presidency.

Because Jackson believed the White House belonged to the people, he invited the people in for a Party after his inauguration. They were unruly as fuck and Jackson had to sneak out the window and stay in a hotel.

He was randomly loving, and adopted three sons, two of whom were Native Americans, and he and his wife were the legal guardians for eight more children.

He was a frail dude, at 6’1″ and weighing around 130 pounds.

By the time he took office, George Washington’s presidency was as far in the past as Eisenhower’s is today.

Here he is looking cranky at age 78.

Last Words: “I hope to meet you all in Heaven. Be good children, all of you, and strive to be ready when the change comes.”

8) Martin Van Buren

Presidency: 1837 – 1841 Lived: 1782 – 1862 Ranking: 24/43

Slave Owner? Yes, but only one (and his father owned six).

His Deal: At 5’6″, the “Little Magician” defined most his career as a passionate advocate for Jacksonian democracy and was one of the key organizers of the 19th century Democratic Party.

His Presidency: He used his time in office to try to continue the policies of Andrew Jackson, but his presidency ended up being swallowed up by an economic crisis called The Panic of 1837, and he was the scapegoat, being nicknamed “Van Ruin.” His situation was not helped by his decision to be elite in front of everyone during the crisis and drive around in the fanciest possible carriages. Not shockingly, he was a one-term president.

Things He Can Brag About:

Being the first president to be born an American citizen

Being the first president not of British origin (his family was Dutch) and first ESL president (his first language was Dutch)

Things He Hopes We Don’t Remember:

The time he was 68 and asked a 40-year-old woman to marry him, and she said no.

Other Notable Facts:

His hometown was Kinderhook, NY, and one of his campaign slogans was “Vote for Old Kinderhook,” or “Vote for OK.” The term OK caught on and it’s theorized that this could be the origin of the word “okay.”

Last Words: “There is but one reliance…” Shame he died before finishing the sentence, and now we’ll never know what the one reliance is.

9) William Henry Harrison

Presidency: 1841 – 1841 Lived: 1773 – 1841 Ranking: 38/43 – welcome to the beginning of the Bad President Circus!

Slave Owner? Yes.

His Deal: Like Andrew Jackson, William Henry Harrison did a lot of pretending to be a common man and a lot of actually being from an extremely wealthy slave-owning family. He was a renowned general in the War of 1812, one of the major reasons he was thereafter a viable presidential candidate. He was the first Whig president.

His Presidency: He started things off with a bang, giving the longest ever inaugural address for two hours. Then he got pneumonia and perished. That was his presidency.

Things He Can Brag About:

Being the only US president to have attended medical school

Things He Hopes We Don’t Remember:

The time he was supposedly morally opposed to slavery, but also owned a bunch of slaves, had six kids with one of them, and fought to legalize slavery in the Northwest of the country to encourage settlement there.

Things He’s Annoyed About:

Dying 30 days into his presidency, a development which impinged upon his ability to rule effectively

Other Notable Facts:

He at one point started making and selling whiskey, but then he realized that whiskey got people drunk, was appalled at himself, and stopped.

He’s the grandfather to future president Benjamin Harrison.

He was nicknamed Old Tippecanoe after his heroics in the Battle of Tippecanoe in 1811, and nicknamed WillyH2 203 years later just now by me.

Last Words: “Sir, I wish you to understand the true principles of the government. I wish them carried out. I ask nothing more.” This would have been such a nice sign-off had it been directed at his successor, John Tyler. Unfortunately, he said this to his doctor.

10) John Tyler

Presidency: 1841 – 1845 Lived: 1790 – 1862 Ranking: 36/43

Slave Owner? Yes, another slave-owning president.

His Deal: A Democrat disenchanted with the Jacksonian loyalists in his party, he was chosen by the opposing party, the Whigs, as William Henry Harrison’s running mate in order to help attract other disaffected Democrats. He was then suddenly the president when Harrison died 30 days into his term. Historians are wholly unimpressed with Tyler, citing his political resolve as one of the only positives of his legacy.

His Presidency: His presidency started in controversy, as the existing Constitution didn’t really have instructions for what to do when a president dies in office (not sure how they could have left this out). It was eventually deemed that Tyler was officially the president, and he began his time in office by ditching the Whigs and Harrison’s existing platform and going rogue with his policies. This turned his own party angrily against him (they called him “His Accidency”), but the opposing Democrats also hated what he was doing, so he was called “a president without a party.” Sounds fun in theory, but the end result was him getting basically nothing done in office and going down as one of history’s worst presidents.

A strong believer in the convenient principle of “manifest destiny,” (i.e. we British descendants are destined to expand ourselves throughout this whole land), about halfway through his term, he became fixated on the goal of acquiring the Republic of Texas. He all but closed the deal, and his efforts set up the next president (Polk) to finish the job.

Things He Can Brag About:

As the governor of Virginia, giving Thomas Jefferson’s funeral address at the age of 36

Things He Hopes We Don’t Remember:

That late in his life, he joined the Confederate Party and was elected to the Confederate House of Representatives, making him the only president to be a sworn enemy of the US

Things He’s Annoyed About:

The Princeton Disaster, when Tyler and his cabinet members were on a ceremonial cruise and a huge naval gun aboard the ship fired a celebratory shot—only it malfunctioned and exploded on the boat, killing off much of Tyler’s cabinet. The scene looked like this.

Other Notable Facts:

He was a prolific impregnator, having 15 children with two wives.



He currently has two living grandchildren, who are ages 85 and 89.



Tyler is the great uncle of Harry Truman.



His wife died of a stroke one year into his presidency, making her the first First Lady to die in the White House. Tyler, 53, then married a 23-year-old (making him the first president to get married while in office).



Julia Tyler, his new wife, began the tradition of having Hail to the Chief played when the president entered the room at state functions.

Last Words: “I am going. Perhaps it is best.”

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