Michigan-based songwriter Timothy Monger began playing music in his teens, working on lo-fi recordings with his older brother Jamie Monger and assorted friends in basements and motel rooms, some of which were later privately released on cassette under the name the Original Brothers of Love. The brothers officially formed the Original Brothers and Sisters of Love with a third songwriter, Greg McIntosh, in 1996, and relocated to Ann Arbor, Michigan, where the group's decidedly creative and postmodern folk-rock approach to songwriting and arrangements earned them a local following. TOBOSOL's debut album, The Legende of Jeb Minor, was released on New York's Telegraph label in 2000, revealing a band with three solid writers who merged a kind of Midwestern Appalachia with solid pop smarts and an offbeat, refreshing lyrical sense.