"The Man Who Sailed Around His Soul" is an existentialist beatnik song that "just says you're born, you live, and you die," Partridge explained. "Why look for the meaning of life when all there is is death and decay." The melody was inspired by the Nat King Cole version of "Nature Boy" (1948). Rundgren's arrangement was based on the music of 1960s spy films, which happened to be in an idiom similar to "Mermaid Smiled". Partridge: "I had in my head that I really wanted to out-do 'Mack the Knife' — the Bobby Darin version. ... it sounded like a spy film title to me. So I thought, 'It'd be great to do sort of a John Barry secret-agent soundtrack thing.' ... I said to Todd, 'Ideally, make it like a Beatnik existential spy movie soundtrack. Can such a thing be done?' And literally, he went away overnight and came back with charts for this stuff." Partridge instructed Prince to drum like a "jazz junkie drummer". On his performance, Prince surmised that he may have unconsciously "channeled" the influence of big band drummer Gene Krupa.