Red text encircled by blue and white checkered border over white background. 

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Purple ombre text over orange checkered background. 

A "cool kid" refers to a young person who is a trendsetter and usually emulated by his or her peers. 

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Con man centered in black text over white background. 

Illustrator Rube Goldberg was born in San Francisco, California and moved to New York City around 1907. The phrase "I'm the guy who" was a trademark expression of Goldberg. He coined it around 1910.  He was well known cartoonist and created "Mike and Ike" and "Boob McNutt" among many other strips.  Later in life, Goldberg help found the National Cartoonist Society (1946) was awarded a Pulitzer Prize (1948) for his political cartoons.

White text over blue background. 

Purple text over white background. 

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Frantic dog runs away from can tied to its tail above black text over white background. 

George Herriman (1880-1944) became a cartoonist despite his father's guidance. He is best known for his 'Krazy Kat' comic strip, which he wrote and illustrated until his death. Herriman made his name known first in Los Angeles, California and later in New York City. In New York City, he worked at the New York Journal and the New York World.

White and black text over red and yellow background. 

Topps, a company that is best known for sports memorabilia, produced "Wise Guy" pins during the 1960s that featured  satire/parody for novelty and humor.

Black ink splotches and fingerprints around black text on white background. 

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Bluce text encircled by red and white diamond border over yellowed background. 

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White silhouette of a man leaning againtst white text on an orange background. 

The leaning figure and slogan were part a 1960s advertising campaign for Klopman fabrics. Klopman began as Klopman Mills, an apparel fabric company, that later merged with Burlington Industries. After the merge, Burlington published multiple department store advertisements of leaning men and women to highlight the Klopman name. With this advertising campaign the company hoped to convey the message that their fabric was reliable, or "something you can lean on."