Thomas Nast (1840-1902) is best remembered for his pictorial attacks on New York's notorious political organization, Tammany Hall and its infamous leader Boss Tweed while cartooning for Harper's Weekly. Using his characteristic pen and ink style, in this drawing, Nast captures patriotic sentiment aroused during New York's first International Naval Review. Held in New York Harbor on April 27, 1893, the event was part of the ceremonies of the Chicago Columbian Exposition, which belatedly commemorated the 400th anniversary of Columbus' 1492 expedition. An international flotilla containing thirty-five vessels of war joined the United States navy, representing the best and most interesting specimens of Old and New World naval architecture, from the caravels of Columbus to the swiftest and most powerful steel-plated cruisers.

Homer Davenport (1867-1912), popular daily editorial cartoonist, created this puckish caricature of his patron William Randolph Hearst (1863-1951) in 1896, the year Hearst brought Davenport from San Francisco to New York and made him the highest paid editorial cartoonist in the country. His cartoons for the New York Evening Journal had such a powerful effect on public opinion that the New York State legislature considered enacting an anti-cartoon bill. Davenport remained a Hearst cartoonist for the rest of his career. William Randolph Hearst retained a coterie of impressive artists for the newspapers, news syndicates, and magazines in his publishing empire.

A World War II editorial cartoon by two-time Pulitzer-prize winner Jay Norwood "Ding" Darling (1876-1962), this work is among numerous landmark images by the leading editorial artists of the past two centuries. Darling drew most of his cartoons when newspapers were the primary source of information and commentary. In this cartoon he portrays Nazi leader Adolf Hitler caught in a bear trap by Soviet forces at Stalingrad in the winter of 1942-43. Hitler's failure to capture Stalingrad and the subsequent Soviet encirclement and defeat of his armies there in that winter marked the turning point in the war in the Eastern Front.

Reuben Lucius "Rube" Goldberg (1883-1970), a versatile talent as a cartoonist and sculptor, is best remembered for his graphic mechanical "inventions." This humorous example reveals how political candidates manage to produce votes. Goldberg personally inscribed his drawing to Art Wood in 1962, the year before he retired from cartooning at the age of 80. He was famous for his so-called Crazy Inventions, and Rube Goldberg's Sideshow, which he produced as comic strips (1939-1941). In 1939 he began drawing editorial cartoons for the New York Sun, then moved to the New York Journal American in 1949, occasionally using crazy inventions as a theme in his work. His drawings typically depict absurdly assembled "machines" functioning in a universe that is a little more accommodating than our own to produce a simple end result. Because of this, his name is associated with any convoluted system to achieve a basic task.