cunliffe described himself as having been drawn to "anything with hip harmony in it" with great melodies, and he loved listening to the 5th dimension, burt bacharach, and herb alpert. he attended phillips academy and graduated in 1974 in the school's first co–educational class. in college, he performed rock and roll at the prince spaghetti house in saugus, massachusetts. he attended wesleyan university for several years. during this time, a friend introduced him to a record by oscar peterson, and after listening to this record, cunliffe became a "jazz player overnight." while in school, he considered careers in medicine and psychology, but in his junior year, he decided finally that "music was it."