Ray Osrin was a staff inker at Jerry Iger's comics shop from 1945 to 1949. In the 1940s, his work appeared at Fiction House and Fox. In 1950 Osrin worked as an inker on It Rhymes with Lust, which is considered one of the most notable precursors of the graphic novel. He was a staff cartoonist of the Pittsburgh Press from 1958 to 1963. In 1963, he "blindly applied for a job in the art department" of The Cleveland Plain Dealer and was hired to replace editorial cartoonist Ed Kuekes. Osrin moved to Cleveland to work as a cartoonist and "wait for his predecessor to retire." He became the paper’s editorial cartoonist in 1966 and remained there until retiring in 1993. Osrin won the National Headliners Club's award for editorial cartooning in 1971. In a 1972 interview, Osrin said "I'm influenced by Oliphant and Mauldin and Herblock. Upon retirement, he moved to Boca Raton, Florida. He donated collections of his cartoons to Cleveland State University and the Cartoon Research Library at Ohio State University in the hopes that his work would "mean something later on and somebody can enjoy it."
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