Brockenborough was added to the Bosstones in 1990 just before the EPWhere'd You Go? and the band's second album More Noise and Other Disturbances, replacing original trombonist Tim Bridewell. He had, however, made a prior cameo appearance on the "Devil's Night Out" music video. Brockenborough's mother was a music teacher at David W. Harlan Elementary School in Wilmington, and his brother was an All-State football player at Salesianum School in Wilmington. He graduated from Brandywine High School, where he served as president of both his class and the band, in the suburbs of Wilmington.
While with the Bosstones, Brockenborough played a Yamaha YSL-691 trombone with a Denis Wick 4C mouthpiece. He also sang backup on songs such as "Kinder Words" and "Simmer Down."