Born in Mount Olive, Mississippi, Magee was raised in St. Petersburg, Florida, where he came of age dabbling as a piano player in local churches and suffering his parents' ire when he drifted into the blues. As a young man he worked local blues clubs under the monicker "Five Fingers Magee" and was billed as "the fastest guitar player in the world." After a stint in Germany as a U.S. Army paratrooper in the 1950s, Magee was demobilized in New York and ended up settling in Harlem. A sometime-songwriter for Jesse Stone, Magee recorded several near-hits on Ray Charles's Tangerine label in the early 1960s, including "Get in My Arms Little Girl." His proficiency on guitar earned him gigs with a number of rhythm-and-blues performers, including James Brown, King Curtis, Big Maybelle, Joey Dee and the Starlighters, and a transvestite duo known as The Illusions That Create Confusion. In the mid 1970s he played sessions with Paul Winley and the Harlem Underground, a loose-knit unit that included George Benson.
In October 1986, Harmonica player, Adam Gussow encountered Magee purely by chance, this time at Magee's regular stretch of sidewalk near the Apollo Theater. Gussow, a semi-seasoned street performer by this point, sat in. The two musicians--one older, African American, and southern-born; the other younger, White, Ivy-educated, a New York suburbanite--hit it off.
What began as a streetside encounter ended up blossoming into a twelve-year success story. The duo's initial notoriety accrued in the summer of 1987, when the members of U2 wandered by Magee and Gussow with a video crew in tow, capturing the Harlem duo at work. Thirty-nine seconds of Magee's original composition, "Freedom for My People" were ultimately included in the Rattle and Hum documentary