His first record album (Devil May Care, released on Bethlehem in 1956 and still available) caused quite a stir. The buzz has continued over nearly five decades since then, with Dorough recordings issued on a variety of labels, both large and tiny. Along the way, Bob became the first and the last halfway decent singer to appear on a Miles Davis record. Among Bob's more illustrious songwriting collaborators over the years have been Fran Landesman and Dave Frishberg. His tunes now appear on albums recorded by dozens of other vocalists and many have found special favor as instrumentals, too.

He is also known for his musical direction of the hit TV show, SCHOOLHOUSE ROCK and for contributing lyrics to both the show and the consequent musical versions of SCHOOLHOUSE ROCK LIVE.