Lil Mama "Lip Gloss" (2007)

Nowadays, hip-hop heads know Lil Mama as the loonbat who crashed the stage during Jay-Z and Alicia Keys' 2009 MTV VMAs performance to mean mug in a B-boy stance. Before that she was a rapper whose "Lip Gloss" hit with a brief wave of teenage New York rappers in the mid-2000s. The beat and chorus jam, but then she takes the song title a little too literally and goes into detail about applying make-up in the verses. The more you listen, the sillier it gets.