Whitehead's articles on jazz and improvised music have appeared in such publications as Point of Departure, the Chicago Sun-Times, Village Voice, Down Beat, and the Dutch daily de Volkskrant.
He is the author of Play the Way You Feel: The Essential Guide to Jazz Stories on Film (2020), Why Jazz: A Concise Guide (2010), New Dutch Swing (1998), and (with photographer Ton Mijs) Instant Composers Pool Orchestra: You Have to See It (2011).
His essays have appeared in numerous anthologies including Da Capo Best Music Writing 2006, Discover Jazz and Traveling the Spaceways: Sun Ra, the Astro-Black and Other Solar Myths.
Whitehead has taught at Towson University, the University of Kansas and Goucher College. He lives near Baltimore.