Pop Culture Rewind explores famous songs written about celebrities, starting with the decades-long mystery of Carly Simon’s "You Are So Vain." The hosts discuss the Britney Spears and Justin Timberlake feud, analyzing tracks like "Cry Me a River" and Spears’ recent memoir revelations. They also cover Ashley Tisdale’s "Boyfriend," the Eminem-Mariah Carey diss track war, and confirm Dave Coulier as the subject of Alanis Morissette’s "You Ought to Know."