A portrait in both film and music of the American musician Lee Ranaldo, the 49-minute film In Doubt, Shadow Him! takes the form of a visual drift in the city where Ranaldo lives and works, and which he has seen evolve, from the underground on up, for more than thirty-plus years: New York City. On the streets of the city, in the maze of subway corridors, in recording studios, artist lofts, and the workshops of his friends and collaborators, a film crew shadowed him through the crowd, and witnessed his meetings and conversations with personalities we recognize from the worlds of music and visual arts. These brief discussions, which float in the ambient hubbub, narrate his personal and musical history.

The film's soundtrack was composed by Ranaldo and French experimental rock quartet Hifiklub during the filming, and recorded at Echo Canyon West in Hoboken, New Jersey. The various tracks, which include performances from many of Lee’s collaborators and colleagues, reflect the various contiguous aspects of the artist's musical work throughout his career. Interestingly, while Lee does play some guitar on these tracks, his concentration, for this project, was on the lyrics and vocal performances, which include a duet with Sarah Register (Talk Normal) on the track Pure.