Steven Paul Smith was born at the Clarkson Hospital in Omaha, Nebraska, the only child of Gary Smith, a student at the University of Nebraska Medical Center, and Bunny Kay Berryman, an elementary school music teacher. His parents divorced when he was six months old, and Smith moved with his mother to Duncanville, Texas. Smith later had a tattoo of a map of Texas drawn on his upper arm and said: "I didn't get it because I like Texas, kind of the opposite. But I won't forget about it, although I'm tempted to because I don't like it there."

Smith graduated from Hampshire College in Amherst, Massachusetts in 1991 with a degree in philosophy and political science. "Went straight through in four years", he explained to Under the Radar in 2003. "I guess it proved to myself that I could do something I really didn't want to for four years. Except I did like what I was studying. At the time it seemed like, 'This is your one and only chance to go to college and you had just better do it because some day you might wish that you did.' Plus, the whole reason I applied in the first place was because of my girlfriend, and I had gotten accepted already even though we had broken up before the first day." After he graduated, he "worked in a bakery back in Portland with a bachelor's degree in philosophy and legal theory".  While at Hampshire, Smith formed the band Heatmiser with classmate Neil Gust. After Smith graduated from Hampshire, the band added drummer Tony Lash and bassist Brandt Peterson and began performing around Portland in 1992. The group released the albums Dead Air (1993) and Cop and Speeder (1994) as well as the Yellow No. 5 EP (1994) on Frontier Records. They were then signed to Virgin Records to release what became their final album, Mic City Sons (1996).  Around this time, Smith and Gust worked a number of odd jobs around Portland, including installing drywall, spreading gravel, transplanting bamboo trees, and painting the roof of a warehouse with heat reflective paint. The pair were also on unemployment benefits for some time, which they considered an "artist grant".  Smith had begun his solo career while still in Heatmiser, and the success of his first two releases created distance and tension with his band. Heatmiser disbanded prior to the release of Mic City Sons, prompting Virgin to put the album out inauspiciously through its independent arm, Caroline Records. A clause in Heatmiser's record contract with Virgin meant that Smith was still bound to it as an individual. The contract was later bought out by DreamWorks prior to the recording of his fourth album, XO.

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