He began playing jazz on the violin while a student at The High School of Music and Art in New York City. While attending college at Manhattan School of Music, Pointer earned a reputation as a session musician. By age 19, his experience as a freelance musician included the Apollo Theater Orchestra, the Love Unlimited Orchestra, the Westbury Music Fair Orchestra, the Radio City Music Hall Symphony, the Love Unlimited Orchestra (US Tour), the Dance Theater of Harlem Orchestra, the Symphony of the New World, and the pit orchestras of several Broadway shows, including "Guys and Dolls" and "Dreamgirls".