18. Missy Elliott "The Rain (Supa Dupa Fly)" (1997)
Album: Supa Dupa Fly
With Y2K just a few years away, Missy Elliott and producer Timbaland decided it was time for the future. Her 1997 debut release, Supa Dupa Fly, was jam-packed with experimental postmodernism, both sonically and lyrically. As the lead single, "The Rain (Supa Dupa Fly)" was the album's magnum opus. Missy was navigating uncharted waters, walking a tightrope between R&B and rap. Straying from female stereotypes of the time, even "The Rain's" explicitly sexual lyrics sound subtle, ("Sway on the dosie-do like you loco/Can we get kinky tonight?/Like CoCo, so-so/You don't wanna pay with my Yo-Yo") opting for clever wordplay over crassness. Missy's stuttering flow matched with Timbaland's syrupy beat to make the song that much more unconventional. Even if came out today, it would still sound ahead of its time. —Alysa Lechner.