After playing in the rock band Heatmiser for several years, Smith began his solo career in 1994 with releases on the independent record labels Cavity Search and Kill Rock Stars. In 1997 he signed a contract with DreamWorks Records, for which he recorded two albums. Smith rose to mainstream prominence when his song "Miss Misery" -- included in the soundtrack for the film Good Will Hunting -- was nominated for an Oscar in the Best Original Song category in 1998.
Smith suffered from depression, alcoholism, and drug addiction, and these topics often appeared in his lyrics. At age 34, he died in Los Angeles, California from two stab wounds to the chest. The autopsy evidence was inconclusive as to whether the wounds were self-inflicted. At the time of his death, Smith was working on his sixth studio album, From a Basement on the Hill, which was posthumously released.
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