As a child he owned a harmonica, and was encouraged by the blues musicianship of his paternal grandfather,[3] who played National steel guitar and had toured across the States.

The academic life did not suit him, and on impulse Pittman bought a harmonica at the age of 26, despite having had no formal musical tuition.

[5] After two years had passed,[3] and noting that both Taj Mahal and John Lee Hooker lived in the San Francisco Bay Area, in 1975 Pittman caught a Greyhound bus to Oakland, California.

[3] In his days in the Bay Area, Pittman met several blues musicians including Sonny Rhodes, Cool Papa Sadler, Jimmy McCracklin, Lowell Fulson, Percy Mayfield, and J.J. Malone.

[5] Pittman variously worked or recorded with Dave Alexander, Sugar Pie DeSanto and the Mississippi Delta Blues Band.