Montgomery was the eldest boy of 16 children.
Music was his first love and he played the guitar as well as the upright bass. He also sang baritone.
He was a fine song writer, penning The Fall Is the Lonesomest Time of the Year (aka The Fall), Foolish Dear to Love You, Short Term Contract and Lonely Waters.
He played with Bill Monroe (1986/1987), Lester Flatt, the Cumberland Mountain Boys, Boys from Shiloh, Dixie Gentlemen, and Rual Yarborough and the Dixiemen, among others.
Montgomery can be heard on albums by The Cumberland Mountain Boys (Nashville Bluegrass Opera, Do-Ra-Me LP 301, 1963); Dixie Gentlemen (Together Once More, Old Homestead OHS 90020, 1973); Rual Yarbrough & the Dixie Gentlemen (California Cottonfields, Old Homestead OHS 90019, 1973); Rual Yarbrough (Just Me, Old Homestead OHS 90066, 1976); Jake Landers (Singer/Writer, Old Homestead OHS 90073, 1976); Lester Flatt (Lester Flatt Live! Bluegrass Festival. With Guest Bill Monroe, RCA Victor APL1-0588, 1974 [later released as Live at Vanderbilt]) and the Bill Monroe album Bluegrass ’87 (MCA 5970).
He toured the country with the legendary George Jones and he appeared in movies with Arnold Schwarzenegger and Sally Fields.