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As the son of two professional musicians, John Boswell grew up in a richly musical and artistic environment. This developed into an interest in musical theater which began in high school and blossomed during his years at U.C.L.A., where he wrote a musical with actor Tim Robbins. Boswell continued on this track after graduation, working on Broadway productions of The Secret Garden and Liza! and the L.A. productions of Berlin to Broadway With Kurt Weill and The Beautiful Lady. He also served as music director for such notables as Judy Collins and Bob Newhart, and composed music for TV shows like General Hospital and Santa Barbara.
Boswell explored the more personal side of his music by performing in the vocal trio Wiseguys and through refined, emotional instrumental albums like The Painter and Kindred Spirits, both recorded for the small, short-lived Scarlet record label. The small but passionate following these records inspired brought him to the attention of the Hearts of Space label, who released 1992's Count Me In and the holiday album Festival of the Heart; subsequently, the label re-released his prior works. Trust followed in 1998, with Love appearing a year later.