Born in San Francisco in 1972, Smith relocated to the mountain town of Gunnison, CO, at 17, making a living playing piano in local clubs. Two years later he settled in Denver, playing attention-grabbing four- and five-hour sets at area venues like the Mercury Café and Muddy's Coffeehouse. Smith continued his nomadic existence in the years to follow, living on an organic farm in the jungles of Costa Rica and busking up and down the Pacific coast. The experience yielded not only songs but also screenplays and short stories, and upon returning to the Bay Area in 1996, Smith abandoned the piano in favor of guitar, crafting the jazz-tinged folk melodies and improvised lyrics that would eventually coalesce into his self-released 2000 debut LP, Who's the Monster...You or Me? That same year he wrote and directed the short film Kid Gus Man, and in 2001 began writing a regular column, Steppin' Out, for The New Mission Newspaper.

By the time the San Francisco label Jackpine Social Club released This Is My Story, This Is My Song in mid-2003, Smith was living across the bay in Oakland's Fruitvale neighborhood. As the record began earning critical praise, he began collaborating with Wilco bassist Leroy Bach, playing a series of Bay Area gigs and in 2004 traveling to Bach's native Chicago to record. Around that same time Smith also released the CD-R Sweet Lorraine: Sordid Tales of Love and Woe, a collection of duets with Jolie Holland, and the literary journal Watchword pressed One Act Plays, a series of story-songs. In early 2005 Smith won a three-month residency at San Francisco's Headlands Center for the Arts, re-recording both Sweet Lorraine and One Act Plays, the latter featuring guest appearances by singers including Mark Eitzel and Edith Frost. He spent the summer of 2006 touring in support of Neko Case, and a year later issued Fruitvale, a song cycle inspired by his stay in Oakland.

In 2007, Smith formed the band Sonny & the Sunsets, which featured a rotating lineup of members including multi-instrumentalist Kelley Stoltz, Tahlia Harbour (the Dry Spells), John Dwyer (Thee Oh Sees), Tim Cohen, and Shayde Sartin (Skygreen Leopards). In 2010, Sonny & the Sunsets released their full-length debut, Tomorrow Is Alright. That same year, the Sunsets also participated in Smith's "100 Records" show in San Francisco, where 100 artists created record jackets by fictional bands for a series of 7"s featuring music created by Smith. ~ Jesse Jarnow & Jason Ankeny