12. De La Soul, De La Soul Is Dead (1991)
Label: Tommy Boy, Warner Bros.
The playful experimentation and layers of in-jokes that made 3 Feet High & Rising such a breath of fresh air eventually backfired on De La Soul and their mentor Prince Paul, who found themselves increasingly pressured to repeat the commercial success of "Say No Go" as Tommy Boy Records continued to milk the "black hippy" angle for all it was worth.
De La responded appropriately by killing themselves (and the D.A.I.S.Y. Age) off. Fortunately for rap fans, this increasingly cynical version of the group proved to be even better at making music, as De La Soul Is Dead was far more accomplished and challenging than their debut. The beats were better, the rhymes were tighter, and the skits were even funnier. They even managed to produce a couple of catchy radio-friendly singles in spite of themselves, as their anti-demo tape rant "Ring, Ring, Ring" became a worldwide smash and infected the answering machines of douchebags across the globe.
With gems such as "Afro Connections at Hi-5" and the epic three-part "Bitties at the BK Lounge," De La proved that they were just getting started.