Smilin' into Nowhere, released in 2000, is Stickpony's debut album. The group held its CD release party with a standing room only crowd at The Hole in the Wall. Brit Jones, Stacey Sperling and Steve MacDonel made up Stickpony when the CD was recorded. Peter Stiles and Gregg Yows also played on the album. The current lineup is Brit Jones, Steve MacDonnel, Alex Crump, and Nathan Fontenot. Jones wrote all but one of the songs on Smilin' into nowhere.

Stickpony formed in 1997. They toured the Midwest in 1998. By 1999 they were working on their first CD with Peter Stiles (formerly of The Meat Purveyors) producing. The Austin Chronicle describes their music as, "literate, melodic twang that manifests itself in songs that cry out for a shot and a beer even as the stories chronicle what a dead-end road that is." Sometimes likened to the tight roots-rock sound of Uncle Tupelo, this group is sometimes alt-country, sometimes punk and sometimes straight rock.

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