In 1970 Montgomery formed The James Montgomery Band. His harmonica playing, singing and energetic stage show led to his band gaining a reputation as one of the hottest bands on the New England music scene. James Montgomery was signed by Capricorn Records to a multi-album deal and released his first vinyl LP album titled The James Montgomery Band – First Time Out in 1973. The original LP recordings were remastered and released as a CD in October 20, 1998 by Capricorn / Umgd. Track 9 off his first album titled "Train" was a fan favorite and became the Number 1 song on WBCN, The Rock of Boston. They played it every day at noon-time for over a year. In 2011, Montgomery brought "Train" back as a surprise encore at shows.
Montgomery has toured with many artists, including Aerosmith, The J. Geils Band, Bonnie Raitt, Bruce Springsteen, The Allman Brothers, The Steve Miller Band, The Johnny Winter Band, The Blues Brothers with (Jim Belushi and Dan Aykroyd) and others.
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