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

The JOAT 50 Song Countdown is a blog series where every weekday for 10 weeks I am posting a brand new long form essay where I have ranked and written about my 50 favorite songs of all-time. From Adele to Zac Brown Band, Patsy Cline to Plasma Canvas, Ludacris to Rise Against, this series offers a personal essay about the 50 songs that hit me the absolute hardest.

In his unparalleled “The Number Ones” column that I reference online and in real life a zillion times, Tom Breihan opens with the following paragraph about Ludacris’ first number one hit “Stand Up” (emphasis mine):

In the early ’00s, the rappers and singers and producers of the world learned an important lesson: You could supercharge a song if you got yourself a Ludacris guest verse. Luda would crash onto every track like a semi truck with its breaks (sic) cut. He would manifest as pure chaos energy — roaring at the top of his lungs, spraying raunch and wordplay and dad-jokes in every direction, never losing total command of the beat. Ludacris was a character, an animated and adrenaline-boosted horndog craftsman with a technically masterful syllabic-spray style and a proudly goofy rubber-chicken lampshade-head partyman persona. Naturally, Missy Elliott figured it out first. Missy figured most things out first.

I came around to Missy Elliott late because, unlike her, I do not figure out most things first, especially when it comes to music. Oddly enough it wasn’t until I had kids that I felt like I was really on top of music because new music was the easiest of the pop culture media to keep up with. Ask me about some show you’re into, I almost certainly haven’t watched it. Movies, the same. But music I could do while parenting, while driving, or while filling out my expenses in a spreadsheet. Compared to the other 40-somethings who either still listen only to shit they liked in high school, or who have been subsumed by the dull, homogenous gruel tarpit of Bro Country, this makes me something of an anomaly.

The interesting byproduct of discovering new music is that discovery begets discovery, whether it’s stuff that came out last month or two damn decades ago. And the only reason I’m pissed about it is that I could have been enjoying Missy Elliott this whole freaking time instead of sleeping on her like a chump. I’m almost as bad as one of those idiots who thinks Katy Perry “discovered” Missy Elliott and gave her a boost by having her perform at Super Bowl XLIX.

When I compiled the very first MVT Playlist from the videos selected by Stephen, Jason, and Kristin, I had no idea what to do with “The Rain.” It was too weird. You know the video. A bunch of it is shot with a fisheye lens. Every rapper in the world makes a cameo mugging directly into camera. Missy wears a huge inflated Hefty bag and flops her arms around while giant swinging gears flank either side of her. She sits atop an obviously phony hill inside a soundstage looking as fat as possible. She sings the words, “Beep beep. Who got the keys to the Jeep? Vrrrrroooooom” and somehow still makes it sound cool.

I thought all this shit while sober, obviously.

Then I watched it while high as balls and up to that point I’m not sure I’ve ever enjoyed a music video more in my entire life. It was then that Missy Elliott snapped into place for me. I followed that by immediately having the desire to mainline Missy Elliott songs directly into me because I remembered all the songs I’d heard in their ubiquity, but never really gave the time of day to.

“Work It” led to “Get Ur Freak On” led to “Gossip Folks” led to “One Minute Man…” ad infinitum. Not only is a Missy technically gifted MC who can spit with speed, she’s clever, she’s unexpected, she’s insightful, and best of all, she’s fucking weird as hell. No Missy Elliott song sounds like another Missy Elliott song, yet they all sound like Missy Elliott Songs. You don’t believe me, but I am not high while I write this.

“The Rain (Supa Dupa Fly)” stands above them all in my mind because it’s somehow Missy’s debut single. This feels like some 7-years-in shit where the audience is daring you to surprise them, so you throw an avant-garde freak track at them to see how they react. Nope! This is Missy announcing herself to the world, and the world (minus me at the time because I’m a moron) responding, “Yes! More of this please!”

When I coach people in public speaking, one of the things I tell them is “Make bold choices, and the universe will reward you for them.” It’s good advice in public speaking because think about every single time you have ever seen someone get up in front of you in some conference room or hotel ballroom. Literally every person in the room is thinking the same thing. God, I hope this doesn’t suck. If you make a strong impression right up front, you’ve bought yourself a runway of goodwill from that audience.

“Make bold choices and the universe will reward you for them” is also excellent life advice because even if you whiff, at least the universe knows you’re someone to be reckoned with, and fuck, at least you tried something different, something courageous, and something interesting.

Missy Elliott clearly lives by this philosophy.

But then, she didn’t need me to tell her that. Because as usual, Missy figured it out first.

Up next: Can you pay the bills, you good-for-nothin’ type of brotha?

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