Born in Cincinnati, Ohio, from 1949 to 1951 Wesselmann attended college first at Hiram College, before transferring to the University of Cincinnati to major in Psychology. After only a year’s study, he was drafted into the US Army but spent his service years stateside. During that time, he fulfilled an ambition to become a cartoonist, and had work published in several magazines. After his discharge, he completed his psychology degree, and began studying at the Art Academy of Cincinnati.
When Wesselmann enrolled at the Academy of Cincinnati, his greatest ambition was to become a cartoonist. In 1956, however, all that changed: he was accepted to study at New York's prestigious Cooper Union, where he met his lifelong muse, Claire Selley. While there, he began transforming his quick sketches into collages using scraps of wallpaper and ads. In 1961- after an enlightening dream conerning the phrase, 'red, white and blue'- he began painting Selley. He called the resulting series The Greatest American Nude, and it launched his status as an art world talent.
In 1980, Wesselmann began his autobiography, documenting the evolution of his artistic career under the psudonym Slim Stealingworth. Written in third person, the book recalled the impact of seeing Robert Motherwell's painting Elegy to the Spanish Republic in the late 1950s-'The first experience... He felt a sensation of high visceral excitement in his stomach, and it seemed as though his eyes and stomach were directly connected'.
Wesselmann was also influenced by Willem de Kooning: 'he was what I wanted to be,' he explained in an interview. As Stealingworth, he wrote 'he realised he had to find his own passion [...] he felt he had to deny to himself all that he loved in de Kooning, and go in as opposite as a direction as possible. The traditional situations of painting would be the subjects: the reclining nude, a still life on a table, a portrait, an interior'. The monogrpah is still to hthis day one of the most accurate and complete examples of the evolution of the artist's work.
In the late 1950s, Wesselmann founded the Judson Gallery in Greenwich Village with fellow artists Jim Dine and Marc Ratliff. This artist-run gallery gave exhibitors the opportunity to escape the constraints of the established art world and make their own rules. It also facilitated collaboration, providing artists with an opportunity to experiment with their work, share ideas and gain feedback- as well as freedom to exhibit without censorship.
After initiating The Great American Nude series in 1961, Wesselmann's career took off. The works reference the fabled Great American Dream and Great American Novel, featuring patriotic colours, as well as motifs suh as stars and stripes. Wesselmann featured in ground-breaking Pop Art exhibitions of the early 1960s, including New Realists at Sidney Janis Gallery, and The Popular Image at the Washington Gallery of Modern Art.