I encountered a rolling stone nyt and can’t tell if it’s literal, idiomatic, or musical. Is it tied to the saying or pop culture? NYT often plays with familiar phrases. Thoughts welcome.
In crossword of NYT, A Rolling Stone? is a pun that is oftentimes used as a hint toward ISSUE, meaning an issue of the music magazine. It may also be an allusion to MOSSLESS (of the proverb) or a band member, such as JAGGER.
In NYT crosswords, “a rolling stone” is often clued as nomad, drifter, or ram (in zoological or zodiac contexts). It plays on the proverb “a rolling stone gathers no moss,” suggesting someone who wanders and doesn’t settle, a common theme in crossword wordplay.