A native of Portland, OR, Smith began writing and recording his first songs at age 14, later becoming a fixture of the city's thriving music scene; as a member of the band Heatmiser, he debuted in 1993 with the LP Dead Air, issuing his first solo effort Roman Candle on the tiny Cavity Search label a year later. For his 1995 self-titled album, Smith signed with the noted Kill Rock Stars label; Either/Or followed in 1997, around the same time that filmmaker and longtime fan Gus Van Sant requested permission to use the singer's music in his upcoming Good Will Hunting.

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