Wolf was born in Washington, D.C., the son of Rosemary and Jack Wolf. His father was born Jewish and his mother converted to Judaism. His earliest experience in broadcasting was on the intercom system of Calvin Coolidge High School in Washington, D.C. in the 1950s. His upbeat, entertaining patter that was to become his trademark made his sports report a welcome treat for the kids. During this period he worked part time at Baker's Shoe Store downtown, as a salesman. Many customers must have been puzzled at the ball park hawker's refrain of, "Get your hot dogs, get your hot dogies here" coming from the back store room. He was simply entertaining the staff and the customers, something he was to continue throughout his long career.