Lear was born in New Haven, Connecticut, the son of Jeanette (née Seicol) and Herman Lear, who worked in sales. He grew up in a Jewish home and had a Bar Mitzvah. Lear went to high school in Hartford, Connecticut and subsequently attended [[Emerson College in Boston, but dropped out in 1942 to join the United States Army Air Forces. During World War II, he served in the Mediterranean Theater as a radio operator/gunner on Boeing B-17 Flying Fortress bombers with the 772nd Bombardment Squadron, 463rd Bombardment Group (Heavy) of the Fifteenth Air Force. He flew 52 combat missions, for which he was awarded the Air Medal with four Oak Leaf Clusters. Lear was discharged from the Army in 1945. He and his fellow World War II crew members are featured in the book "Crew Umbriago" by Daniel P.Carrol