Smith began playing regularly in and around Austin, both on his own and as part of a bluegrass band called the Ramblers. In time, Smith developed a significant local following, and in 1986, he recorded his debut album, Native Soil, which included guest appearances from Lyle Lovett, Nanci Griffith, and Joe Ely. Originally released on Smith's own Redi-Mix label, Native Soil was soon picked up for release by the noted Texas independent label Watermelon Records, and the album brought Smith to the attention of Epic, who signed him to a record deal. Three songs from Native Soil reappeared on Smith's self-titled Epic debut, which produced two minor hit singles, "Little Maggie" and "Day After Tomorrow." But while Epic chose to market Smith as a country act, his music began became more introspective as his songwriting matured, and in 1989, he released a collaborative album with British songwriter Boo Hewerdine, Evidence. In time, Epic handed Smith over to the pop music division of their sibling label Columbia Records, and his next two albums, 1990's Trouble No More, and 1993's Little Victories, won good press, while the song "Loving Arms" scraped the lower levels of the Top 100 singles charts. Uncertain of how to market Smith, Columbia dropped him from their roster, and in 1996 he released Deep Fantastic Blue through the independent Plump Records imprint. In 2000, Smith re-recorded a handful of his best-known songs for the album Extra Extra, and 2002 saw the release of Sunflower, his first album for Dualtone Music. Smith cut two more albums for Dualtone, 2004's Circo and 2005's Field of Crows, followed by a limited-edition live album, 2006's Ojo. Ojo was issued by Smith's own Darden Records, which also issued a studio album, 2010's Marathon, and a 2009 compilation, After All This Time (The Best Of). Artist-friendly independent label Compass Records issued 2013's Love Calling, and Smith issued Everything, his 15th album, in April 2017. Everything featured guest appearances from Beth Nielsen Chapman, Kelly Willis, David Mansfield, Charlie Sexton, and Roscoe Beck.
In addition to his work as a songwriter and performer, Smith is also part of several creative outreach programs. Founded by Smith in 2001, the Be an Artist Program was designed to encourage creative expression among young people at risk. Smith is also one of the founders of SongwritingWith:Soldiers, in which gifted songwriters work with soldiers and veterans to use music as a means of dealing with the trauma of combat. And he's also lent his talents to academic and private organizations as part of programs designed to bolster creative thinking. ~ Mark Deming, Rovi