Thomas Nast, Honoré Daumier, Bill Mauldin, David Low, Theodor Geisel, Herblock, and good grief, more Herblock! In honor of some sort of election that's apparently coming up, Comics Should Be Good! will be featuring one ink-stained satirist every day this October! Visit the Stars of Political Cartooning Month Archive for daily updates.
The political cartoons of Clifford K. Berryman lampooned American politics from the era of Grover Cleveland to the Truman administration. If he's known today it's mostly for having originated the teddy bear. While some of his cartoons have scant relevance today, many remain surprisingly relevant. Of the many historical events he drew there are women's suffrage, the 1948 election and the 1912 Republican primaries between Taft and Roosevelt.
Enduring Outrage: Editorial Cartoons by Herblock, an LOC exhibition. From 1950s plutocrats to 1970s ethics scandals, and up to the ideal American Flag of the religious Right, Block captured complex issues in just one frame. His drawings about government limitations of civil liberties seem particularly prescient.
Searchable database of >120,000, reasonably high-resolution editorial cartooons. Mainly from the UK, and from the last 100 years. Search by person depicted (e.g., Thatcher, Gorbachev, Thatcher and Gorbachev); by year (e.g., Hitler and Stalin in 1941 or 1942), by design elements (e.g., cartoons referencing sculpture by Rodin, or cartoons with zebras), by topic (e.g., BSE, Falklands War), by artist (e.g., William Hogarth, L.G. Illingworth, Carl Giles, Steve Bell) or by publication outlet (e.g., Punch, Evening Standard (over 10,000 from Evening Standard alone). There is a handy searching wizard as well.
Punch Cartoons Punch set the standard for Victorian satirical cartooning. The Victorian Web hosts a number of cartoons arranged according to topic; see also Punch on the British Empire. Some students in Anthony Wohl's senior seminar at Vassar did a good job annotating a number of images. You can find late Victorian cartoons, as well as cartoonists' biographies, here. Of course, the current incarnation of Punch has a few things to say about its own history.
The Tragedy in Cartoons. One of the more interesting effects of a national tragedy is that it always somehow causes the nation's editorial cartoonists to suffer massive, collective brain damage. Across the country, they rush to their easels and whip up cheesy, embarrassing caricatures of Uncle Sam crying. Or the Founding Fathers crying. Or - in this case - a comparison to Pearl Harbor. Or - if your local cartoonist is feeling particularly creative - the always crowd-pleasing weeping Statue of Liberty. As Cagle notes, "Fully half the nation's cartoonists drew the same cartoon on the same day." Including Cagle himself. A tragedy in cartoons indeed. Some psychiatrist really ought to study this phenomenon.
WTC Editorial cartoons I don't know if they trivialize or symbolize, but they're often part of the artifacts we use to remember events like this.