Bryan started playing the trumpet in fourth grade and studied with Vincent Macrina through high school in Brockton, MA. Bryan then studied with Jeff Holmes and the late Walter Chesnut while attending the University of Massachusetts at Amherst, from which he graduated Magna Cum Laude. While at UMass, Bryan played lead trumpet in Jazz Ensemble I, and received both an Outstanding Musician Award from the International Association of Jazz Educators and a Downbeat Award from Downbeat Magazine.

As college was winding up, he found the funk and joined Rippopotamus, a Boston-based funk/rock band. During Bryan's tenure with Rippo, the band opened for a variety of national acts, including Queen Latifah, Phish, Fishbone, De La Soul, and the Beastie Boys. Rippo released five albums, wrote and performed the theme song for MTV's dating show Singled Out, and were a featured act at the Montreal Jazz Festival. They also won a 1996 Boston Music Award.

In 2001, Bryan founded Occasional Brass, a Boston-based brass quintet. An all-around player, and in addition to his work with Occasional Brass, Bryan can be heard around Boston playing weddings, musicals, funk, rock, big band, dixieland, salsa/merengue, and even a circus gig or two.