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.

Painted image of a tan face half covered in brown shadow and dark brown hair in front of a yellow and brown background. 

This hand painted button was created by an unknown artist and found in a closet in Wicker Park, Chicago. 

Pink, green, yellow, and white illustration of a woman's face in profile with stars, stripes, and spades designs.

Peter Max (b. October 19, 1937) is a German-born American illustrator and graphic artist, known for his use of psychedelic shapes and color palettes. His bright, colorful work was often imitated in commercial illustration in the late 1960s and early 1970s. 

Photo image of W.C. Fields playing cards with the cards held close to his face. The image is tinted orange, yellow, and green. The name "peter max" appears at the bottom of the button in pink text surrounded by a black line border. 

Peter Max (b. October 19, 1937) is a German-born American illustrator and graphic artist, known for his use of psychedelic shapes and color palettes. During the late 1960s and and early 1970s, Max used intense bursts of color in his work, incorporating many colors in one image. He also often used popular American icons, celebrities, and symbols in his work, such as as the actor W.C. Fields.

W.C. Fields (January 29, 1880 – December 25, 1946) was an American actor, comedian, juggler, and writer. He was known for his comic persona as a pessimistic, aggressive and suspicious-natured men with great fondness of alcohol.

Painted image of four heads with orange faces; two with blond hair, one with light brown hair, and one with dark brown hair sitting in dark blue water with light blue dots on a light blue background. 

This hand painted button was created by an unknown artist and found in a closet in Wicker Park, Chicago. 

Illustration of a young girl in a red dress with white hair and large white eyes on a white background with black text in the lower right corner.

One of a series of 86 different comic character buttons issued by Kellogg's and given away with PEP cereal between 1945-1947. Other characters in the series included Dick Tracy, Popeye and Felix the Cat.

Little Orphan Annie was a daily American comic strip created by Harold Gray that was first published in 1924 and ran until 2010. The comic featured the adventures of Annie, the little red-haired orphan, and her dog, Sandy.

Abstract design of alternating blue and red lines and orange and green dots on a white and gray background. 

This image is a hand painted button. It was created by an unknown artist and found in a closet in Wicker Park, Chicago. 

Cartoon illustration of an orange face with brown wavy hair, eyes closed, and a yellow hand pinching a long nose. 

This cartoon face illustration of a nose holder 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.