Raised by his grandparents in Reading, MA, Simon Stokes was seen by his peers as a loner or solitary child. By the age of ten he had become a sleepwalker. His grandfather would often take Stokes to see the Harry D. Stokes Orchestra, which was his introduction to music. In his teenage years, Stokes became influenced by the blues, often listening to a local DJ named Sid Symphony and attending all-night concerts. Stokes saw Big Mama Thornton and Hank Ballard among countless others, each having an impact on him. After entering a local songwriting contest and winning the top prize, Stokes ventured to Los Angeles in his early 20s. Beginning in 1965, Stokes recorded a number of 45s under names such as the Flower Children and Heathen Angels. At the same time, Stokes became a staff writer at Elektra Records. Forming a band called the Nighthawks, Stokes and MC5 signed to Elektra on the same day.
In 1973, Stokes released his debut album, Incredible Simon Stokes, on Spindizzy Records. The album was a psychedelic blues record in the vein of Captain Beefhart. That same year, Stokes released Simon Stokes & the Black Whip Thrill Band on Spindizzy. The album's cover was reportedly the first banned album cover in the United States. Featuring S&M scenes as well as females being whipped, the controversy created a cult following for the musician, especially among biker groups. In 1977, Buzzard of Love was released. After this album, Stokes basically went underground, releasing no material for nearly two decades. In 1996, he returned to music circles by releasing Right to Fly which he did with '60s counter-culture icon Timothy Leary. In 2002, Stokes released a country-rock album titled Honky. Featuring members of the Bellrays and Wayne Kramer, the album's sound was compared to outlaw singers such as Waylon Jennings and David Allan Coe.