42. Leaders of The New School "Case of the P.T.A." (1991)
Producer: Cut Monitor Milo
Album: A Future Without A Past
Leaders of the New School's legacy has been dwarfed by that of group member Busta Rhymes, but the group had an accomplished career in its time that goes well beyond the "Scenario" guest spots that stole the show on Tribe's Low End Theory.
Released the same year as that album, L.O.N.S.'s "Case of the P.T.A." was a play on the group's name. Over a jazzy irreverent Ramsey Lewis sample, the trio tossed back and forth high school tribulations about dealing with parents and teachers while trying to play pranks and score with the ladies.
Compared to the rap that would come soon after, there's an innocence about it. Not that it's wholesome, exactly—Charlie Brown the class clown ends up in a courtroom by the end of his verse—but the lighthearted approach to the subject matter definitely feels of its era. —David Drake