Olsen was born in Chicago to Elsie Anderson and Andrew P. Olsen, a commercial designer for Kleenex and other products. After a stint in the U.S. Navy during World War II, he attended the School of the Art Institute of Chicago on the GI Bill and participated in student Exhibition Momentum shows in 1948, 1950, and 1952. He moved to New York City in 1952 and exhibited at the Bodley Gallery (1955), Rhode Island School of Design Museum (1956), Grace Borgenicht Gallery (1958), and two Whitney Museum of Art annual shows. In the early 1960s he married and began working at Kulicke Frames, which influenced his work on Plexiglas in that decade. He painted figural work in the 1970s through 1990s, then experimented working with magic marker and poured paint in his last decades. In 2001 he exhibited recent work at the Greene Community College Art Gallery. In 2012 he had a posthumous retrospective at the Athens (NY) Community Art Center.
In 2010, his son-in-law Joshua Seiden made this short video of Earle talking about his work.