The answer to “How does it...” in Bob Dylan’s “Like a Rolling Stone” is “feel.” The question anchors the song’s confrontational chorus, challenging its subject to face life after privilege, status, and security have disappeared.
Dylan wrote the song in 1965 after returning exhausted from a demanding English tour. He first produced a much longer piece of prose and verse, then distilled it into four verses and a chorus. The finished recording became the opening track of Highway 61 Revisited and helped establish Dylan’s electric rock direction.
The six-minute single initially worried Columbia Records and some radio programmers, who considered it too long. Public demand helped overcome that resistance, and the song reached No. 2 on the U.S. Billboard chart. A common mix-up is treating it as a straightforward love song; its tone is instead satirical, accusatory, and fascinated by the freedom that can follow a complete loss of social standing.