Date: 2000

Most Ignorant Line: “Hung out with you on Mother’s Day, because your mother's dead.”

What happened? When Stan’Ron dissed Cam—his former mentor—in an obscure freestyle, Cam let off this career-ending diss track, "Dear Stan." The song flips Eminem’s classic about a suicidal male groupie into a lyrical homicide.

Complex says: Saying the meanest shit you can think of just to win a rap battle is one thing, but when you talk about someone’s deceased mother, even if you win (and Cam’ron clearly did), you will always lose.