O'Sickey attended East Tech High School in Cleveland from 1934 to 1937 while also attending Saturday morning classes at the Cleveland School of Art (now Cleveland Institute of Art). He also took advantage of free evening classes at the John Huntington Art and Polytechnic Institute. Upon graduating from high school in January 1937, he continued his studies at the Cleveland School of Art. In March of 1941, he was drafted into the Army where he spent 26 months of his four years and ten months in service overseas in Africa, India and Burma. Since it was difficult to obtain painting materials, O'Sickey focused on drawing with whatever medium and paper was available. He still owns the drawings from this period because he felt it was at that time that he really learned how to draw.
In early 1946, O'Sickey had an encounter that would be the single most important moment in his life-meeting Algesa D'Agostino at the 1030 Gallery. In August 1947 they were married. During that time, O'Sickey spent the summer of 1946 traveling through the American West with Cleveland artists John Paul Miller and Paul Travis. Upon his return, O'Sickey found employment at the Ohio State University. While at OSU, O'Sickey was influenced by his informal study with Hoyt Sherman and began a life-long friendship with fellow faculty member Roy Lichtenstein. Although he was offered continued employment after his year at OSU, O'Sickey returned to Cleveland and Algesa.
From the late 1940s into the early 1960s, he worked at a variety of jobs in Cleveland- many of them at the same time. In 1950 O'Sickey's son, Joel Benjamin, was born. In 1956 he was hired to teach Beginning Design at the School of Architecture at Western Reserve University. In 1962 he bought a house in Deer Isle, Maine that would become his and Algesa's summer home for 31 years. However, his life dramatically changed in 1964 when he received an appointment as Assistant Professor of Art at Kent State University, and he continued teaching at Kent through his retirement in 1989.
In 1963, O'Sickey began his longtime relationship with the Jacques Seligmann Galleries in New York City. Upon their closing in 1978, he began a relationship with Kennedy Galleries in New York until 1994. Locally he has been represented by Vixseboxse Art Galleries and The Bonfoey Gallery. He has won numerous awards in painting at the annual May Show of the Cleveland Museum of Art. He was selected to receive a 2013 Governor's Award for the Arts in Ohio in the individual artist category, and he has had more than 50 one-person shows throughout his life. (Bio from Canton Museum of Art)
