From the age of 16, Brown played ukulele at social events. He acquired much of his early repertoire from and was stylistically influenced by the records of Cliff Edwards, the Clash, Bob Wills and Trini Lopez. He played regularly at the Landmark Pub in Brooklyn, New York during the late 1980s, where he challenged the boundaries of contemporary live music and championed public space. In the early 1990s, Brown developed an underground reputation for his ukulele renditions of Sweet Jane, All Along the Watchtower and Uncontrollable Urge, while his originals There's a Girl at the Deli, Milk Boy and Va-Va became Pacific Coast college radio mainstays.