20. Three 6 Mafia f/ UGK & Project Pat "Sippin' on Some Syrup" (2000)
Producer: DJ Paul
Album: When the Smoke Clears: Sixty 6, Sixty 1
It might be difficult to remember, now that sipping on codeine cough syrup is a nationally-renowned trend, but when Three-6 first brought this practice to the country's attention in 2000, it seemed to seep from some dark corner of American culture. With a minor-key Marvin Gaye sample (the opening notes of "Is That Enough?" from Here My Dear), "Sippin on Syrup" oozed eerie, lascivious anti-charm.
Unrepentant in its embrace of casual drug abuse and non-traditional sexual liaisons (at least via DJ Paul), the song still feels radically transgressive. But it's also one of the best posse cuts in rap history, if only for Pimp C's unforgettable opening boast about keeping dope fiends higher than the Goodyear blimp, and Bun B's Duke Ellington reference (yes, of course Bun listens to "Perdido" while sipping on that Texas tea). —David Drake
Best Verse: Pimp C