This drawing is by Thomas Nast, a pictorial reporter with the New York Illustrated News who would later go on to work as a political cartoonist for Harper's Weekly. In the drawing, a large group of men congregate in the lobby of the famous Willard Hotel in Washington, D.C. on March 6, 1861, just two days after President Abraham Lincoln's first inauguration. Notable among the men is Horace Greeley, the editor of the New York Tribune, who stands conversing with another man on the right. The German-born Nast is widely considered to be one of the premiere political cartoonists in American history, famous for his early 1870s crusade against William Marcy "Boss" Tweed in New York City.

This satirical political cartoon entitled "Latest from America" depicts Albert Edward, the Prince of Wales and the future King Edward VII of Great Britain, preparing to relay to his father Albert, Prince Consort, stories of his tour through the United States. The caption reads "H.R.H Junior (to H.R.H. Senior). 'Now, sir-ree, if you'll liquor up and settle down, I'll tell you all about my travels.'" "Punch, or The London Charivari," a weekly British humor magazine published the cartoon on November 10, 1860.

This stipple drawing of President Martin Van Buren was created by David Claypool Johnston from around 1840. This political cartoon involves the 1840 election, where President Van Buren, then serving as the 8th president of the United States, lost his reelection. In this image Van Buren is smiling, holding a gold goblet with the initials MVB. The gold goblet represents the perception that Van Buren had a regal lifestyle while President. This image is one of two of Van Buren before the election and after the election. Please see image 916 for Johnston's other engraving of President Van Buren.

This stipple drawing of President Martin Van Buren wsa created by David Claypool Johnston from around 1840. This is a political cartoon referencing the 1840 presidential election as President Van Buren sought reelection. The initials of "WHH" on the cup refer to William Henry Harrison and the text on the bottom of the image states, "An Ugly Mug of Log Cabin Hard Cider." The log cabin hard cider referred to Harrison, President Van Buren's opponent during the election, who was presented to the American public as a man from rustic beginnings in contrast to Van Buren's wealthier background.

This illustration, titled "The Fall of Washington or Maddy in Full Flight," was created in October 1814 by Samuel William Fores, also known as S. W. Fores. This British cartoon depicts the retreat of President James Madison during the invasion of Washington, D.C. by British troops in the War of 1812. Underneath the illustration is a quotation from William Shakespeare's "Macbeth." It reads, "Death of thy Soul. Those linen cheeks of thine; Are Counsellors to fear."

This political cartoon by Clifford K. Berryman shows a teddy bear, representative of President Theodore Roosevelt, pondering the question, "To Go or Not to Go?" It is dated March 2, 1909, which is two days before his term as president ended, and is emphasized by the moving van loading crates in the background. The crates read, "T.R. Africa" and "T.R. Africa/Handle With Care." This is likely in reference to the Africa expedition Roosevelt took just after he left office on behalf of the Smithsonian Institution to expand its holdings.

This political cartoon illustrates the discourse surrounding a possible third term in office for President Theodore Roosevelt. Roosevelt served two terms as president from 1901 to 1909 as a Republican and ran for a third term on the Progressive Party, or "Bull Moose" Party, ticket in the 1912 election.