While the work done in the Screaming Trees was much more energetic and fit into the burgeoning
grunge genre of the late 80s/early 90s,
The Winding Sheet has a much more stripped-down sound, defining Lanegan's solo work largely for the rest of the decade. As Lanegan recounts in his 2017 book
I Am the Wolf: Lyric and Writings, "Prior to this I had sometimes written words with the other members of my first band, or, more often, had tried to change their lyrics to fit me in a more personal way. This was a tedious, frustrating routine that was never enjoyable, and so
The Winding Sheet became my first attempt at going it alone." Notable music photographer
Charles Peterson shot the cover image of Lanegan. During the selection of the album's cover art, Lanegan specifically demanded that a different photo of himself be used on the cover, stating that the label's preferred shot seemed "pretentious". When the album shipped without the cover art being changed per the agreement between him and Sub Pop co-owner
Bruce Pavitt, Lanegan stormed into Pavitt's office at Sub Pop, berating him and threatening him with legal action and various acts of violence, and threatened to have the albums pulled from store shelves. ==Recording==