While two songs landed in the top 50 of the Billboard mainstream rock charts and he received two Independent Music Awards, he remained on the fringes of both the blues and alternative-rock worlds.

[4] His parents "grew up on race radio in the South" and their musical tastes—including Muddy Waters, Howlin' Wolf, Bob Dylan and Jimi Hendrix—influenced Whitley.

[6] At the age of fifteen Whitley taught himself to play guitar[3] by ear, inspired by Jimi Hendrix and Creedence Clearwater Revival.

[4] From 1977 until 1981, Whitley was busking on the streets of New York City and then collaborated with musicians Marc Miller, Arto Lindsay and Michael Beinhorn.

[2] In 2001, The New York Times described him as "restless, moving into noise-rock and minimalist jazz evoking Chet Baker and Sonic Youth as much as Robert Johnson".

[12] He recorded songs by Robert Johnson and Bob Dylan as well as Lou Reed, James Brown, J.J. Cale, The Clash, Nat King Cole, The Doors, Willie Dixon, The Flaming Lips, Jimi Hendrix, Howlin' Wolf, The Jesus and Mary Chain, Kraftwerk, Gary Numan, The Passions, Prince, The Stooges, and Sonny Boy Williamson II.

[17] In 2004 he won The 4th Annual Independent Music Award for Blues/R&B Song for his composition "Her Furious Angels" from the album War Crime Blues.

[18] Whitley was an inaugural member of The Independent Music Awards' judging panel to support independent artists[19] After his death, musician John Mayer said, "[Whitley's] somewhat prostrated place in pop culture earned him a sidebar of an obituary, but to those who knew his work, it registers as one of the most underappreciated losses in all of music.

[14] Notable fans of Whitley's music include, ATO co-founder Dave Matthews,[15] blues guitarist Robert Lockwood, Jr., Bruce Springsteen, John Mellencamp, Bruce Hornsby, Tom Petty, Jacob Golden, Myles Kennedy, Don Henley, Iggy Pop, Alanis Morissette, Sandi Thom, John Mayer, Gavin DeGraw, Joey DeGraw, Johnny A., Joe Bonamassa, Keith Richards and Darling Burns.