• 2025 National Endowment For the Arts “Jazz Master”
• Ralph J. Gleason Music Book Award for Bing Crosby: A Pocketful of Dreams, 2002.
• National Book Critics Circle Award in Criticism for Visions of Jazz, 1999.
• ASCAP Gerald Marks Award, 1997. This award was given only once, to acknowledge the fact that Gary Giddins won the ASCAP Deems Taylor Award in music criticism more than any other writer.
• ASCAP-Deems Taylor Award for Music Criticism, 2004.
• AAN (Association of Alternative Newsweeklies): Music Criticism, Second Place, 2004.
• Jazz Journalists Association Award, Lifetime Achievement, 2003.
• Jazz Journalists Association Award, Jazz Writer of the Year, 2003.
• Jazz Journalists Association Award, Jazz Writer of the Year, 2002.
• ARSC Award for Excellence in Historical Research for Bing Crosby, 2002.
• Theater Library Association Award for Bing Crosby, 2002.
• Jazz Journalists Association Award, Jazz Writer of the Year, 1999.
• Jazz Journalists Association Award for Visions of Jazz, 1999.
• Ralph J. Gleason Music Book Award for Visions of Jazz, 1999.
• AAN (Association of Alternative Newsweeklies): Music Criticism, First Place, 1999.
• ASCAP-Deems Taylor Award for Faces in the Crowd, 1992.
• George Foster Peabody Award, John Hammond, 1991.
• Grammy Nominee for album notes, Art Pepper on Galaxy, 1990.