[1] Pitts learned to play guitar at age 11 on the street corners of his childhood hometown, Washington D.C., often receiving tips from his neighbor, Bo Diddley.

Pitts' uncle owned a hotel next to the Howard Theater, where he was introduced to soul and R&B musicians such as James Brown and Otis Redding.

In the 1990s and 2000s, Pitts collaborated with Hayes on the John Singleton remake of Shaft as well as the soundtrack for the animated series South Park, for which he received a gold record.

His guitar riffs have been sampled by Dr. Dre with Snoop Dogg, Beastie Boys, Massive Attack, Eazy-E, and DJ Shadow with Cut Chemist.

In 1998, Pitts became a founding member of The Bo-Keys, a soul/jazz group formed by producer Scott Bomar as an homage to Memphis' rich musical tradition.

He appeared with the band at venues and festivals nationally and internationally, including The Ponderosa Stomp, London's Barbican Performing Arts Centre, and Lincoln Center's Midsummer Nights Swing Series.

In addition to Wattstax and Truck Turner, Pitts appeared in the award-winning Forty Shades of Blue, Craig Brewer's Black Snake Moan, and Soul Men featuring Bernie Mac and Samuel L. Jackson, for which he also contributed three songs to its soundtrack.