While acting in an off-off-Broadway play called "Rockabilly Road", Hipp met singer-songwriter Carole King, with whom he acted in the two-character "A Minor Incident" on Theater Row and performed in concert at The Royal Albert Hall. It was during this first visit to England that he landed the title role in the London production of "Buddy: The Buddy Holly Story", a part he would reprise for his Broadway debut in 1990. For his performance as Holly, he earned a Laurence Olivier Award nomination, a Tony nomination and a Theatre World Award and Hipp garnered significant recognition in the entertainment industry. Since then he has starred as George Berger in the 25th anniversary revival of "Hair" at the Old Vic and as singer Gene Vincent in "Be Bop A Lulu" at the Theatre-Theater in Los Angeles.
On TV, Hipp debuted as Elvis Presley in the CBS biopic "Liberace: Behind the Music" (1987) and starred in "Legacy", the pilot for a proposed NBC midseason replacement series. He has also guest starred on episodes of "Men Behaving Badly", "Nash Bridges" and "Tales From the Crypt", among others. His role as Joe Odom, the fast-talking, party-loving tax attorney reprobate in Clint Eastwood's feature adaptation of the John Berendt novel "Midnight in the Garden of Good and Evil" (1997), displayed Hipp's musicianship (this time at the piano) and offered him his best exposure since his turn as Buddy Holly.