16. De La Soul, De La Soul Is Dead (1991)
Label: Tommy Boy
Not many groups have the balls to kill themselves off, especially after a successful debut that featured "Me, Myself & I," which topped Billboard's R&B charts two years earlier. But the title of De La's sophomore masterpiece was more than just a (successful) attention-grabber; it was a mission statement. The Long Island trio was determined to shed the happy-hippy image of their first album's so-called D.A.I.S.Y. Age, and this LP, with its darker subject matter, deadpan deliveries and murky loops, did just that.