Deciding to pursue a solo career after the band, La-Di-Das, broke up, Chesnutt would play solo at the 40 Watt Club. It was there that R.E.M. frontman, Michael Stipe, first spotted Chesnutt and helped him to produce his first album. It was released on Texas Hotel Records in 1990.
The most elemental of any of Chesnutt's albums, it features just his warbly voice and precarious acoustic guitar, occasionally accompanied by Stipe's keyboard flourishes. As its title suggests, Little is about Chesnutt's Pike County childhood, a theme he would return to repeatedly as if thumbing worn and creased snapshots found at the bottom of a drawer. "Rabbit Box" begins, "While I was still in elementary school I discovered Daddy's tools," following the songwriter as he builds a rabbit box out of scrap lumber, but only catches a cat and a possum. In one sense, his youth represents an uncomplicated time-- pre-crash-- when all of life's possibilities lay before him, before they were whittled down to the point they are now.