Born in Boston, Massachusetts, Sudhalter was inspired to pursue a musical career by his father Al Sudhalter "(né" Albert W. Sudhalter; 1905–1975), a noted Boston-area saxophone soloist. Dick began playing the cornet at 12 and within a few years was performing professionally. After graduating from Oberlin College, he moved to Europe in 1964, later becoming a United Press International correspondent. In 1968 he covered the Russian invasion of Czechoslovakia from Prague for UPI and was subsequently assigned the role of Manager for Eastern Europe. During his twelve years living in Europe and the UK, he also wrote under the pseudonym "Art Napoleon." He wrote jazz criticism for the "New York Post" from 1978 to 1984.