Gobel graduated from Chicago's Theodore Roosevelt High School in 1937. Initially a country music singer, he appeared on the National Barn Dance on WLS radio and, after service in World War II, turned to comedy. During World War II, Gobel served in the United States Army Air Forces as a flight instructor in AT-9 aircraft at Altus, Oklahoma and later in B-26 Marauder bombers at Frederick, Oklahoma. In a 1969 appearance on The Tonight Show with Johnny Carson, Gobel joked, "There was not one Japanese aircraft got past Tulsa.