87. De La Soul, 'De La Soul Is Dead'
On their second album, De La Soul turned away from the "daisy-age" friendliness of their 1989 debut in favor of sleeker, head-snapping jams and skits that viciously sent up gangsta rap. The album's hypnotic sprawl centered around producer Prince Paul's sampleriffic beats (see the disco-rap classic "A Roller Skate Jam Named 'Saturdays'"); the guys also took on some brave subject matter (on the disturbing incest tale "Millie Pulled a Pistol on Santa") while preserving their dextrous, clever rhyme styles. The result was a dark classic that was both stranger and deeper than most people noticed back in 1991.