With Shadowland, the tours since 2010 formed a trilogy, the concept being life in reverse. Talking Light focused on death and ghosts, Wonder of Weird on sex and life, and Shadowland was concerned with birth and reincarnation.

Unlike the previous shows, Shadowland did not have a narrative running throughout. Indeed, apart from introducing the band and explaining the concept at the beginning, the only word Randy spoke (that were not part of songs) was "Shadowland," which was how he introduced the video segments.

In January of 2016, Charles Bobuck announced his plans step away from the touring side of The Residents. His last performance with the group was at SXSW, where the documentary film Theory of Obscurity premiered. In later performances he was replaced by a new member, Rico.

Shadow Stories is a 25-minute piece which incorporates the audio from the video segments of the Shadowland Show. It is intended to be a companion to the released Shadowland CD which, due to being limited to a single CD, edits out several songs and all of the video segments.

This was a handmade CDR with a handwritten label, limited to 100 copies, and only made available at the Santa Cruz performance of Shadowland (which was considered a release party performance for the CD, which came out that week).