The compilation is composed of nine tracks from his first four DreamWorks albums: 1999's How Do You Like Me Now?!, 2001's Pull My Chain and 2002's Unleashed, as well as five new recordings. Three of these new recordings are studio tracks, of which two ("Stays in Mexico" and "Mockingbird") were released as singles, reaching #3 and #27, respectively, on the Hot Country Songs charts. "Mockingbird", a cover of the Inez and Charlie Foxx hit, features Keith's daughter Krystal as a duet partner.
Two newly recorded live renditions are also included on this album: one of Keith's debut single "Should've Been a Cowboy" (originally from his self-titled debut album), and another of his 1995 single "You Ain't Much Fun" (originally from Boomtown).