In 1965, Bob Brown—hailing from Clinton, Maryland, with an arsenal of Dylan covers—began his annual hitchhikes to the Newport Folk Festival. With both a natural talent and a yen for self-promotion, he built a solid following in the D.C. area, opening for any folkie with a respectable following who happened to pull through town. A chance encounter with Richie Havens in Provincetown, Massachussetts, lead to a friendship, which culminated in a record deal with Havens’ label, Stormy Forest.
At his core, Brown was a classic troubadour, but the band he put together was far more expansive. His debut LP, The Wall I Built Myself, was a freeform folk-rock LP with jazzy elements. Its modest success earned fans and friends from the upper strata of the folk scene, including such luminaries as Tim Hardin and Eric Anderson. Brown’s frequent tours with Richie Havens blessed him with an audience, but he struggled to emerge from his mentor’s shadow. Brown’s sophomore effort, Willoughby’s Lament, was more or less a flop, but it finally fulfilled the obligations of his contract with Stormy Forest.
Brown’s relocation to the Chelsea Hotel in Greenwich Village put him in regular contact with both the misfit and elite classes of the bustling scene. From his Chelsea room, he wrote diligently, demoing “Close Of The Day” for a third album with George Massenburg that never materialized. After a deal with Columbia fell through, Brown dove into a downward spiral, leading out of music and onto a path towards motivational speaking and writing the celebrated guide The Little Brown Book Of Restaurant Success.