22. EPMD, "Strictly Business"
The best thing about EPMD's inaugural single is the duo's self-produced beat – a cornucopia of blatant samples from the golden age of artistic pilfering, with Eric Clapton's "I Shot the Sheriff" busting wildstyle moves on the floor next to Mountain and Kool and the Gang. Erick Sermon and Parrish Smith's laid-back rhymes were revolutionary, too. Most rappers in 1988 were still stuck on the brash cadences that town criers from LL Cool J to Chuck D favored; EPMD's casual, goofy approach to the mic laid the groundwork for generations of chilled-out MCs.