16. Beastie Boys, 'Paul's Boutique' (1989)
Dense with about 105 samples and more hilarious references than anyone could count, Paul's Boutique is a pop-culture Finnegans Wake of a rap album. Co-produced with sampling demons the Dust Brothers during hip-hop's pre-clearance golden age, it's the equivalent of a Hollywood pre-Code masterpiece. Arriving three years after the trio's debut, Paul's Boutique was downright avant-garde compared to 1986's highly successful, Rick Rubin-produced, anthem-laden head-banger Licensed to Ill. And while the Beasties still specialized in perfectly pitched self-deprecating braggadocio, every laugh line about owning "more suits than Jacoby & Myers" was balanced by a self-aware notion like "expressing my aggressions through my schizophrenic verse words."