With Louis Armstrong as inspiration, Herb Pomeroy chose the trumpet as his instrument. By age twenty-five, he had performed with Charlie Parker, toured with Stan Kenton and Lionel Hampton and recorded with Serge Chaloff. Herb Pomeroy became known as a "musician's musician," a leader in big band jazz, an improviser of uncommon stature, a legendary educator at the Berklee College of Music for forty-one years and founder and director of the Festival Jazz Ensemble at MIT for twenty-two years.
By the age of twenty-two audiences already had identified Pomeroy as an exceptional trumpet player. He left Harvard University after one year to join the legendary Charlie Parker Quintet