The album consists of outtakes from the previous several years, when she was in the process of recording Dragging a Dead Deer Up a Hill. A photograph of Harris' mother is featured on the cover art.
In a press release, Harris explained the title The Man Who Died in His Boat:
When I was a teenager the wreckage of a sailboat washed up on the shore of Agate Beach. The remains of the vessel weren't removed for several days. I walked down with my father to peer inside the boat cabin. Maps, coffee cups and clothing were strewn around inside. I remember looking only brieﬂy, wilted by the feeling that I was violating some remnant of this man's presence by witnessing the evidence of its failure. Later I read a story about him in the paper. It was impossible to know what had happened.
Speaking of the main protagonist implied in the title of the album, Drowned in Sound columnist Tim Peyton writes: "The mysterious pathos of this incident suits Grouper well. As Harris explains, 'the boat never crashed or capsized... (it) just slipped off somehow. And the boat, like a riderless horse, eventually came back home.' This haunting return of an unmanned vessel is spooky in a similar way to Harris's ethereal, multi tracked vocals."