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Join, or Die
Benjamin Franklin's woodcut of a snake cut into pieces, each piece labeled with the initials of a colony or region, ran in his Pennsylvania Gazette on May 9, 1754, as war with France over the Ohio Valley loomed and he pressed the case for a colonial union at the Albany Congress.
Its genius is how little it needs: three words and a severed body that anyone could read at a glance. The image outlived its original purpose, reappearing in newspapers during the 1765 Stamp Act crisis and as a masthead during the Revolution, when the unity it demanded was turned against Britain rather than France. Start here to see how a single picture can carry an argument further than any editorial.
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The Plumb-pudding in danger
James Gillray's etching, published by Hannah Humphrey in February 1805, seats William Pitt and Napoleon at a dinner table, each carving a slice from a pudding that represents the world.
It skewers the hope, then being floated, that Britain and France might settle down together, and history bore it out: the two kept fighting for another decade. Neither man is spared, which is a large part of its charm. The cartoonist Martin Rowson has called it probably the most famous political cartoon of all time, and the image of leaders carving up the globe has been borrowed so often since that seeing the original feels like meeting the ancestor of a whole family of jokes.
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Elkanah Tisdale
The Gerry-Mander, Boston Gazette, March 26, 1812
Elkanah Tisdale turned a Massachusetts electoral map into a winged, clawed monster, mocking the state senate districts redrawn for the Democratic-Republican Party and signed into law by Governor Elbridge Gerry. Nobody knows who coined the name, but the cartoon fixed it in the language, and the word is still the first one reached for whenever district lines look suspicious. Few cartoons can claim to have handed a whole political vocabulary a new noun and verb. The trick worked, too: the party kept control of the legislature, which is a reminder that a cartoon can win the argument and still lose the vote.
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Honoré Daumier
Born
Gargantua, lithograph for La Caricature, December 1831
The young Honoré Daumier drew King Louis-Philippe as Rabelais's insatiable giant, enthroned and gulping down bags of coins hauled up a ramp to his mouth by tiny laborers. The French state took the joke personally. Daumier and his publisher were tried in February 1832, fined and sentenced to six months in Sainte-Pélagie prison. That sentence is what makes the print historic: it is an early, vivid case of a government treating a caricature as a threat, and of an artist whose career only grew from the punishment.
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Thomas Nast
Born
Who Stole the People's Money?, Harper's Weekly, 1871
Thomas Nast drew Boss Tweed and his Tammany Hall circle standing in a ring, facing outward and passing the blame around, a single image that summed up a whole city's corruption for readers who would never follow the accounts. It belongs to the campaign that helped bring the Democratic machine down, and legend has it that Tweed ordered someone to stop those pictures. The final twist is the best: after Tweed escaped to Spain in 1875, an official there recognized him from a Nast cartoon. Few drawings have done more to show what caricature can do to a powerful man.
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The Bosses of the Senate
Joseph Keppler's color lithograph for Puck, January 23, 1889, fills the back of the Senate chamber with towering, top-hatted moneybags, each one a trust, looming over the small senators at their desks while the public gallery's entrance stands shut.
It is the Gilded Age in one picture, and it has never really left the classroom, turning up in textbooks whenever monopoly and political money come up. The target is a system rather than a party, which is why it still lands: change the labels on the bags and it could run this week. Look at the scale above all, since the whole argument is in how big the bosses are and how small the lawmakers look beneath them.
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Dropping the Pilot
John Tenniel's Punch cartoon of March 29, 1890 shows Otto von Bismarck, dressed as a ship's pilot, walking down the gangway while the young Kaiser Wilhelm II watches from the deck above.
Bismarck had just been dismissed, and Tenniel caught the British worry that Germany, steered by an emperor Britain trusted far less, might drift off course without the man who had guided it. The quiet staging is the point: no exaggerated faces, only one figure leaving and another left in charge. Readers who know Tenniel only as the illustrator of Alice will find the same precise line put to sober political use, and the title still reads as shorthand for any capable adviser shown the door.
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The Rhodes Colossus
Edward Linley Sambourne's Punch cartoon of December 10, 1892 turns Cecil Rhodes into a modern Colossus of Rhodes, one foot at the Cape and the other at Cairo, stretching a telegraph wire the length of Africa.
It was drawn as a comment on Rhodes's Cape-to-Cairo dream, and it works on two levels at once: a giant striding over a continent can be read as a bold scheme or as breathtaking arrogance. That double edge is why it became the shorthand picture of the Scramble for Africa. Few cartoons show so clearly how the meaning of a drawing can shift with its readers, with a whole continent reduced to the ground beneath one man's boots.
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Clifford K. Berryman
Born
Drawing the Line in Mississippi, Washington Post, November 1902
On a Mississippi hunting trip that month, Theodore Roosevelt refused to shoot a bear that had been captured and tied up for him, and Clifford Berryman drew the President turning away from the helpless animal. The cartoon's afterlife is extraordinary: the Brooklyn toy and candy maker Morris Michtom made a small stuffed bear in response, and the teddy bear was born. It is the gentlest entry here, a cartoon that flattered its subject rather than wounding him, and a useful reminder that some of the form's lasting influence has come through affection rather than attack.
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David Low (cartoonist)
Born
Rendezvous, Evening Standard, September 20, 1939
As Germany and the Soviet Union divided Poland between them, David Low drew Hitler and Stalin meeting over the body of a dead Polish soldier, amid smoke and ruins, doffing their hats and greeting each other with the insults each had spent years hurling at the other. Low exposed the cynicism of their pact more sharply than any editorial could, and he did it from London at the very start of the war, attacking both dictators at once. The grim politeness is what makes it unforgettable: two men who loathe each other exchanging courtesies over a corpse.
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Philip Zec
"The price of petrol has been increased by one penny. Official.", Daily Mirror, March 5, 1942
Philip Zec drew a torpedoed sailor clinging to a raft in an empty sea, to remind readers what merchant seamen risked bringing fuel to Britain. The government read it very differently. Home Secretary Herbert Morrison likened it to Goebbels, calling it a message telling seamen not to go to sea, and for a while it looked as though he might close the Daily Mirror as he had closed the Daily Worker. The caption, rewritten from Zec's blander line by the columnist William Connor, is what gave the drawing its sting. It is the classic case of a cartoon whose meaning escaped its artist, and of how nervous even a democracy at war could be about one picture.
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Herblock
Born
The cartoon that coined "McCarthyism", Washington Post, March 29, 1950
Early in Senator Joseph McCarthy's hunt for Communists in government, Herblock drew the Republican elephant being urged up onto a teetering pile of tar buckets, the top barrel labeled with a new word: McCarthyism. The name stuck, and it now stands for reckless accusation far beyond the Senate. What makes the cartoon brave is its timing, drawn while McCarthy was rising rather than falling, and its angle: the warning is aimed at the senator's own party, asked to stand on something that cannot hold it. Plenty of cartoons have attacked a politician, but very few have given the dictionary a word.
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Supermac (cartoon)
Vicky, the cartoonist Victor Weisz, first drew Harold Macmillan as "Supermac" in the Evening Standard in November 1958, dressing the Conservative prime minister in a superhero's costume to mock his air of effortless command.
The joke turned on its maker. The nickname caught on, and rather than deflating Macmillan it seemed to enhance his standing with the public, handing him a heroic label that suited him rather well. It earns its place as the great cautionary tale of political cartooning: ridicule only works when the audience shares the cartoonist's scorn, and a catchy image can end up doing the target's publicity for him.
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Leslie Illingworth
Born
Kennedy and Khrushchev arm wrestling on hydrogen bombs, Daily Mail, October 29, 1962
The day after Khrushchev announced he would withdraw his missiles from Cuba, the Welsh-born Leslie Illingworth drew the two leaders locked in an arm wrestle, each seated on a nuclear bomb with a finger still on its detonating button. Where others might have drawn relief, Illingworth drew the danger that remained: the crisis was over, but the means of ending the world was still within reach of both men. It is even-handed in the best way, blaming neither side and both at once, and it is still one of the first pictures reached for to explain what the Cuban Missile Crisis felt like.
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Bill Mauldin
Born
The weeping Lincoln Memorial, Chicago Sun-Times, November 23, 1963
The day after John F. Kennedy was assassinated, Bill Mauldin drew the seated statue of Abraham Lincoln with its head bowed in its hands. There is no joke, only one president mourning another, and it said what a stunned country could not yet put into words. Mauldin had already won Pulitzer Prizes in 1945 for his wartime cartoons and in 1959 for his editorial work, but this is the drawing that shows the form at its most economical. The original is now held by the John F. Kennedy Presidential Library. It belongs here as proof that a political cartoon can record a national moment without attacking anyone at all.
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Ali Farzat
Born
Assad hitching a ride with the fleeing Gaddafi, 2011
During the Arab Spring, the Syrian cartoonist Ali Ferzat drew President Bashar al-Assad clutching a packed suitcase and frantically thumbing a ride from a fleeing Muammar Gaddafi. In August 2011 masked gunmen pulled Ferzat from his car and beat him, concentrating on his hands and breaking his fingers, and told him not to satirize Syria's leaders. The same year he was named a winner of the Sakharov Prize. It is the starkest reminder on this list that drawing a dictator's recognizable face can still cost the artist dearly, and that a single image of a leader packing his bags can frighten a regime more than any speech.
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Ann Telnaes
Born
The rejected Washington Post sketch of billionaires kneeling before Trump, January 2025
Ann Telnaes, a Pulitzer winner in 2001, drew Jeff Bezos, Mark Zuckerberg and other powerful figures kneeling with bags of money before a towering Donald Trump, then President-elect. The Post, owned by Bezos, declined to run it, and Telnaes resigned, writing that it was the first time a cartoon of hers had been killed because of who or what she chose to aim her pen at. The paper said the decision was about repetition of its own columns, not the target. The sketch became famous precisely because it was never printed, and it is the clearest recent case of the old question at the heart of this list: who decides what a cartoonist may draw.
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