Whitley was born in Houston, Texas. He spent the first decade of his career in Belgium, where he recorded several albums and saw moderate success.
Though relatively unknown to the mainstream, he worked with many top named musicians throughout his career. In 1991, U2/Peter Gabriel producer Daniel Lanois and his protégé, Malcolm Burn, recorded Whitley's Stateside debut album Living With the Law. Two of his singles charted in the United States on the Billboard Mainstream Rock charts: "Big Sky Country" and "Living with the Law" Others like Dave Matthews and Bruce Hornsby also appeared on 2001's Rocket House. Whitley played a brand of confessional acoustic and electric blues, mixed with modern rock. His lyrics often contained overt sexual references and sometimes bordered on the surreal. An avid fan of jazz legend John Coltrane, Whitley played the National/Dobro, made famous by many of the great Mississippi delta blues players of the 1930s.
In fall 2005 it was revealed that Whitley was terminally ill with lung cancer. He died on November 20, 2005; his brother, Dan, and daughter, Trixie, publicly announced his passing.
Although Whitley wasn't a mainstream act, his passing resonated throughout the music community and garnered coverage and press throughout the world, ranging from Time, the New York Times, and National Public Radio to a tribute mention at the 2006 Grammy Awards. His albums Living With The Law and Dirt Floor are regarded as classics, and passionate advocates abound for any of his dozen or so other releases, from the hard rock driven Din Of Ecstasy to the somewhat more experimental sound of Rocket House to the dark, jazzy minimalism of Hotel Vast Horizon. Bruce Springsteen, Bruce Hornsby, Tom Petty, Don Henley, Iggy Pop, Alanis Morissette, John Mayer, Gavin DeGraw, and Keith Richards all count themselves admirers of Whitley's music. Dave Matthews has said, "I feel more passion for his music than I do for my own.