Pleissner was born in Brooklyn, New York and educated at the Brooklyn Friends School; however, he spent his two summers at a boys camp in Dubois, Wyoming and a third summer at a dude ranch. The rugged western scenery captivated him and he captured it in sketches. From 1922 to 1926, he studied at the Art Students League (Manhattan, NYC) with Frank DuMond, George Bridgeman and Frederick J. Boston. He then taught at the Pratt Institute in Brooklyn, New York from 1930 to 1934 and the National Academy of Design from 1935 to 1936. In 1942 II Pleissner joined the United States Air Force as an artist in the Historical Division and trained to become a captain, and in 1944 became a war correspondent/illustrator for Life Magazine. Pleissner had attended DuMond’s summer drawing classes in Cape Breton, Nova Scotia, where DuMond introduced him to Atlantic salmon fishing. Always an avid sportsman—he hunted fowl and game and fished the rocky rivers and coasts of the United States, Canada, Nova Scotia and the moors of Scotland, and captured the action in his paintings. He also painted the rivers and coastlines of France, Italy, Portugal, Bermuda, and the Bahamas. Pleissner considered himself to be… “a painter of landscapes who also liked to hunt and fish”, and his experience with, and knowledge of, hunting and fishing equipment and techniques, along with extraordinary drafting skills, made him one of the finest sporting artists of the 20th century. Theodore Gordon Flyfishers, Inc., a nonprofit organization that was founded to promote catch-and-release fly fishing and sound stream conservation practices, selected Pleissner to create their inaugural image. In addition he created sporting prints for the organization Pleissner was a member of the National Academy; Society of American Etchers; Allied Artists of America; American Watercolor Society; Brooklyn Society of Artists; Century Association; Philadelphia Watercolor Club; Baltimore Watercolor Club; Salmagundi Club; Connecticut Academy of Fine Arts; Audubon Artists; Lyme Art Association, among others. He exhibited at the Pennsylvania Academy of the Fine Arts (1928, 1933-49, 1952-53); Corcoran Gallery (1928-53); Harlow MacDonald Gallery (NY, 1930); MacBeth Gallery (NYC, 1930–1950s); Audubon Artists (1950, Medal of Honor; 1954, award; 1969, President’s prize); American Watercolor Society (1956, gold medal); Century Association (1958, 1960, Medals of Honor); National Academy of Design (1959, Altman Prize; Samuel F.B. Morse Medal of Honor; 1961, 1972, gold medals); ,Carnegie Institute; Art Institute of Chicago; National Academy of Design (1959, Altman Prize); American Watercolor Society (1956, gold); Metropolitan Museum of Art; National Arts Club (1928-31, prizes); Salmagundi Club, (1935, 1938, prizes); Whitney Museum of American Art (1938-56); Knickerbocker Artists (NYC, 1974, gold medal of honor); American Watercolor Society (Dolphin Fellowship, Medal); and the Philadelphia Watercolor Club (Joseph Pennell, medal). Pleissner was also the director and trustee of the Tiffany Foundation.