37. Missy Elliott "The Rain (Supa Dupa Fly)" (1997)
Album: Supa Dupa Fly
Label: The Goldmind, EastWest, Elektra
Armed with an Ann Peebles sample and Timbaland at her side, Missy "Misdemeanor" Elliott waltzed onto the rap scene with an out-of-this-world style. "The Rain" is best remembered for its Hype Williams-directed video, but take a listen to it today and you can still hear how startlingly original it was and still is.
The strings on the beat hit like raindrops on your window pane as Missy weaves her way through the track. For all the talk about how lyrics have declined in hip-hop, everyone should peep her playful words ("Beep beep, who got the keys to the Jeep? Vroom!")—and be reminded that even in hip-hop, sometimes the lyrics just aren't the main point.
Missy was always an anomaly. Like Busta Rhymes and ODB, she was a true original who was genuinely left field. Ironically, in the late aughts, as weirdos became more in vogue in hip-hop, Missy was no longer active in the scene even though her influence wasn't hard to see. —Insanul Ahmed