10 of the Most Memorable Fictional Characters in Music

We talk a lot, here at Flavorpill, about our favorite characters from books, film, and TV. And, although we’ve made a habit of compiling mixtapes for everyone from Nancy Drew to Josef K, it isn’t often that we consider the music world’s own fictional creations. After the jump, we attempt to right that oversight with an incredibly subjective roundup of music’s most memorable characters. Add your suggestions in the comments; if we get enough great ones, we might just publish a follow-up post of reader picks.


Rock was a fairly macho domain in 1970, which makes it all the more impressive that The Kinks scored an international top-ten hit with “Lola.” The song is, of course, a four-minute celebration of the narrator’s romantic encounter with a transvestite who turns out to be the perfect, dominant counterpart to his somewhat meek sexual persona. “Lola” is based on Kinks manager Robert Wace’s drunken night of dancing with a cross-dresser, although to our knowledge, his encounter didn’t go further than that. Either way, who wants to bet that the single was many ’60s suburban teens’ first introduction to the wonderful world of gender non-conformity?