Abstract design of a red circle inside of a yellow multi-pointed star shape on a black background. 

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Illustration of a man's head with his mouth wide open and tongue sticking out with yellow text on a blue background. 

This button is from the 1965 series of LEAF "Fink Buttons" illustrated by popular Mid-Century artist Basil Wolverton. Perhaps best known for his work at MAD Magazine, Basil Wolverton (July 9, 1909 – December 31, 1978) was an American cartoonist and illustrator famous for his humorously grotesque drawings. Wolverton worked in the "Golden Age" of comic books doing features like "Powerhouse Pepper" and "Spacehawk" in the 1940s. A 2009 New York Times article states that Wolverton’s drawings embodied the “sick-and-proud humor” of MAD magazine and were considered a “virtuoso exercise in bad taste, made all the weirder for being so meticulously executed.” 

Abstract design of overlapping black spirals on a white background. 

The visual distortion in the spiral optical illusion design is caused by combining a regular line pattern (the circles) with misaligned parts (the black and white dashes),  so the spiral appears to be in motion. Some artists who have worked with optical illusions include M. C. Escher, Bridget Riley, Salvador Dalí, Giuseppe Arcimboldo, Marcel Duchamp, Oscar Reutersvärd, Victor Vasarely and Charles Allan Gilbert. 

This design was produced by the Underground Uplift Unlimited, a slogan button and poster head shop ran by Randolfe Wicker on St. Marks Place in East Village between 1967 and 1971. Wicker closed the shop after becoming disillusioned with pot and psychedelic culture.

Illustration of a smiling man's face with a wrinkly forehead; when the button is turned upside down the man is frowning. Black and red text on a white background.

Advertisement for Champion, an American brand of spark plugs. Champion was a Fortune 500 company founded in Boston in 1908. Their National Spark Plugs Change Week became the accepted time for car dealers and mechanics across the country to perform spark plug checks. 

Illustration of a man's face with two hands protruding from his forehead. Yellow text on a red background. 

This button is from the 1965 series of LEAF "Fink Buttons" illustrated by popular Mid-Century artist Basil Wolverton. Perhaps best known for his work at MAD Magazine, Basil Wolverton (July 9, 1909 – December 31, 1978) was an American cartoonist and illustrator famous for his humorously grotesque drawings. Wolverton worked in the "Golden Age" of comic books doing features like "Powerhouse Pepper" and "Spacehawk" in the 1940s. A 2009 New York Times article states that Wolverton’s drawings embodied the “sick-and-proud humor” of MAD magazine and were considered a “virtuoso exercise in bad taste, made all the weirder for being so meticulously executed."

White text and an illustration of a buffalo and of a donkey on a brown background. 

This button is most likely related to the 1901 Pan-American World Fair Exposition held in Buffalo, New York. The exposition was from May 1 through November 2, 1901. It was intended to showcase trends, developments and innovations of the time.

"RUA Buffalo (picture of a buffalo) U Can (picture of an oil can) Bet Your (picture of an urn) Ass (picture of a donkey) I am" was used on souvenir tokens for the 1901 Pan-American World Fair Exposition in Buffalo, NY. 

Are you a Buffalo? was a phrase used in relation to the exposition.

Red, black, and blue illustration of four stick figures holding hands and two red balloons beneath blue outlined clouds and a solid black skyline. Blue and red text on a white background. 

This button was designed as a contest entry by artist Caleb Lyons for the 1996 Rochesterfest in Rochester, MN. As the winner of the button design contest Caleb won a trip to Florida with his family. 

Cartoon illustration of a smiling face with curly red hair and purple eyes with long eyelashes on an orange background. 

This cartoon face illustration of a curly hair and large eyelashes is part of a series of buttons by an unknown artist. The faces are intended to elicit lighthearted humor and depict exaggerated features or expressions to elicit laughs. This series was created at Colonial Sales, a greeting card and stationary shop in Massachusetts.

Abstract design of alternating red and blue rectangles divided by a white line. 

This illustration is part of a series of buttons that were distributed at the Park Place Gallery in New York, the first art gallery in SoHo. According to an Art in America article, they were given out during the opening show in 1966 and at a party for the Rolling Stones at the Scene discotheque. The buttons were designed by different artists including Dean Fleming, Tony Magar, Tamara Melcher, Patsy Krebs, and Steve Vasey. According to Fleming, the colorful geometric designs encourage the viewer to interpret the art in their own way.

Cartoon illustration of a purple face with green eyes, large nose, and a wide grin with white teeth. 

This cartoon face illustration of a toothy grin is part of a series of buttons by an unknown artist. The faces are intended to elicit lighthearted humor and depict exaggerated features or expressions to elicit laughs. This series was created at Colonial Sales, a greeting card and stationary shop in Massachusetts.