18. Missy Elliott “The Rain (Supa Dupa Fly)” (1997)

Album: Supa Dupa Fly

Label: The Goldmine/Elektra

Producer: Timbaland

Peter Rosenberg:“A lot of people would have probably put one of the Missy songs from the early 2000s when she dominated, like ‘Work It’ or ‘Get Your Freak On.’ To me, ‘The Rain’ was awesome, because I remember thinking, ‘What is this? What is this video? What is this song? Who is this person?’ And Missy went on to be everything she was in that video. She is a totally different and creative and brilliant artist.

“She’s had moments I didn’t love that I didn’t think was her style, where I was like, ‘Why is Missy talking about that?’ But she’s an awesome producer, and incredible writer, and she can sing, and rap. She’s this totally different person, and you knew it the moment you saw her sitting wearing trash bags in this bizarre video with this bizarre beat. And, on top of that, it was one of the first moments we saw how ill Timbaland was.”