Aside from Saturday morning classes at the Cleveland School of Art, Stroup is a self-taught artist. He spent most of his adult life as a magazine editor, first at Town & Country, then at House and Garden, and began to draw only after moving to Nantucket Island. Working initially in felt-tipped pen, Stroup depicted the flat Nantucket landscape, but turned to watercolor after his first exhibition. On the recommendation of a friend, who explained that the drawings failed to sell because Stroup used no color, he bought a set of watercolors. In 1976, having found acrylic an unsatisfactory medium, Stroup began working in his now-preferred medium of oil. Currently concerned primarily with the figure, Stroup creates a sense of enigmatic relationships among the small groups of people he portrays.
Virginia M. Mecklenburg Modern American Realism: The Sara Roby Foundation Collection (Washington, D.C.: Smithsonian Institution Press for the National Museum of American Art, 1987)
Jon Stroup taught himself about contemporary art in the galleries and museums of New York City, where he lived for many years. He worked as an editor for Town & Country and House & Garden magazines, and did not begin making art until he retired to Nantucket Island in the 1970s. He started with felt-tipped pens, but switched to watercolors, acrylics, and oils after a friend told him he would sell more work if he used more color. Stroup creates figurative paintings inspired by his surroundings on Nantucket, and exhibits his work in the island's galleries.