Ranking the Best Songs on Missy Elliott’s Supa Dupa Fly

25 years ago today, my fave gave me the best graduation gift ever.

A month after high school graduation, Missy “Misdemeanor” Elliott dropped her groundbreaking debut album – one that still firmly resides in my top 5 albums of all time.

Y’all know how much music I listen to, yet Supa Dupa Fly will always be a part of my Mount Rushmore. That says a lot.

Today, our anniversary series continues. I’m joined by the homie Deland Wilson to rank and revisit the best moments of this critical piece of hip-hop history. And hey, I get to be a stan for once in one of these posts! No wonder why y’all love stanning so much, it’s fun!

Your pick for Supa Dupa Fly’s best song is…

Deland: Hit ‘Em Wit’ Da Hee”

This song is literally the epitome of WHO Missy actually is as an artist!! The rhymes, the smooth vocals, the Lil’ Kim feature…simply perfection.  Especially with it being the first song on the album after that dope Busta intro, it really set the tone for her artistry to shine and it succeeds quite beautifully.  

Edd: “Beep Me 911”

I went back and forth on my top two spots – 25 years later and they’re pretty interchangeable. I’ll go with “Beep Me 911” for now because that song has had me in a  chokehold for 25 summers. The production, the features (which we’ll get to later), the overall otherworldly vibe – it’s a song that still feels totally unique and fresh decades later. A futuristic bop, as the children might say.

This album is known for its groundbreaking production. Which beat is the best?

Deland: “Beep Me 911”

Timbaland REALLY outdid himself on this joint!!  There was NOTHING out on the radio like this at the time or STILL even up to THIS point RIGHT NOW!!  The staccato drum pattern & stabby bassline mixed with the baby laughs & sped-up soulful wails makes this song a gem!!  Far ahead of his time in that era & proving WHY he had to continue to switch his style up, Timbaland married the future of hip-hop/ R&B with his production.

Edd: “The Rain (Supa Dupa Fly)”

I feel like it’s the obvious answer, but if it’s obvious that makes it the correct choice, right? I LOVE “Beep Me 911” and “Sock It 2 Me,” but there’s something so simplistic yet otherworldly about “The Rain.” The Ann Peebles loop, those pavement-cracking percussions – it’s the most instantly recognizable beat on this record for a reason.

What’s the album’s best feature?

Deland: 702 & Magoo

Now we all KNOW that Magoo was no Rakim or Nas & he was more like a novelty rapper…one there to add flavor, no depth.  But his rhymes couldn’t have been appreciated MORE than on this track.  Adding that last piece of ‘special’ to this song was genius & it connected men & women alike.  Missy is a visionary & it showed by her recruiting her OWN protégés (with slightly better vocals) that SHE helped, assist HER on this song…the result?  Audio butter.  They spazzed on this song vocally, they all compliment each other well & it shows on the silky delivery.  Meelah’s strong soprano pierces through this song softly while Missy’s full alto caresses the beat to where it all just bounces effortlessly…I love it!!

Edd: Magoo

I WILL NOT ACCEPT MAGOO SLANDER. Like the homie said, he’s no Rakim, but next to Lil Oozing Fleshwound, NFL Tattletale and the rest of today’s Mumble Militia, Maganoo sounds like Marshall Mathers. His verse here is utterly ridiculous but there’s actual technique and cadence that adds to the track. DIP N’ DIVE, STAYIN ALIVE! Don’t you miss the days when hip-hop was fun?

This album also produced iconic music videos. Which one reigns supreme?

Deland: “The Rain (Supa Dupa Fly)”

OMG!!  Where do I even BEGIN?!  This was SUCH an inventive & innovative video, it could NEVER be denied even if you didn’t like the SONG (which was like ‘ehhh’ for me).  From the memorable ballooned trash bag outfit to her sitting on ‘hills like Lauryn’ to the fisheye lens perspective ALL OVER..this video gave you EVERYTHING!!  Definitely groundbreaking…

Edd: “The Rain (Supa Dupa Fly)”

This one is a no-brainer. “The Rain” is one of those videos where you remember exactly where you were when you first laid your fisheyes on it. It was hip-hop surrealism come to life, a twisted vision of Missy’s boundless creativity that gave us memes before we even knew what memes were. She and Hype Williams crafted an absolute masterpiece, one of the greatest videos of all time. Due to the legacy of this video, Missy constantly raised the bar in an attempt to outdo herself, giving us years of groundbreaking visuals along the way.

The most underrated song on the album is…

Deland: “Don’t Be Commin’ (In My Face)”

Finding an identity inside of the hip-hop/soul era seemed to be the challenge that ALL new artists were RISING to & it was awesome to see in real time.  Futuristic funk seemed to be how Missy & Tim rose to THEIR challenge & THIS song was a slept-on filler song that I felt really encompassed that.  She sings of how she don’t want no fake love…especially now that she’s on, all while doin’ it to another funky Timbaland beat with catchy cadences & bouncy rhymes.

Edd: “Don’t Be Commin’ (In My Face)”

Bet you thought I was gonna pick the Ginuwine or Aaliyah joints, didn’t you? Well, Deland’s speaking facts. Though it’s been done to death in 2022 (almost always by far less talented artists) the rap/sung thing was still a rarity in 1997 and Missy had the pipes and the swag to pull it off effortlessly. And as Deland said, it’s amazing that this song STILL sounds futuristic 25 years later. Plus, I absolutely loved the way she shouted out Va first and foremost on this track. Hearing my home state get love on record was a rarity back then and it still makes me smile.

And the most overrated songs goes to…

Deland: “Sock It 2 Me”

Never did like this song.  I hated the beat.  I hated the video.  Maybe it’s because of Da Brat.  She irritates me.  After her successful  Funkdafied era (which I really enjoyed)…I was just over her.  Because after that, she always came across as trying waaay too hard when she didn’t HAVE to & it got mad annoying REAL quick.  When she does her little dialogue on this song to kill time…I can actually FEEL my insides cringe.  Let’s just please move on…

Edd: “Friendly Skies”

WAIT WAIT WAIT. Da Brat slander? On this blog!? I won’t stand for it! But I’ve been riding with most of your responses so far so I’ll let it slide for now. Besides, I have more pressing issues – like coming up with the most overrated song on an album with ZERO overrated songs. I’ll guess I’ll pick nits and say “Friendly Skies,” only because I’ve seen some folks name it among the album’s best moments. It’s a solid album cut, sure, but it’s far from a top-tier track.

Which song should have been a single?

Deland: “Don’t Be Commin’ (In My Face)”

As I referenced earlier, this song was a jewel that actually could’ve replaced that Brat song as the second single.  It was funky & Missy carried it nicely by herself…but I see what she was tryin’ to do.  She was setting herself up for something bigger by aligning herself with what was hot at the time & she succeeded.  Still should’ve been a single though.

Edd: “Best Friends”

This is another tough one because everything that could have been a single was made into a single. I guess I could cheat and say that I wanted the album version of “Hit Em with Da Hee” instead of the remixed version that received video treatment. Don’t get a playa wrong, that one was good too but the original is still king. Instead I’ll pick “Best Friends,” which I’m sure would have given us a wacky but heartwarming video celebrating sisterhood.

Twenty-five years later, how influential is this album?

Deland: Missy’s Supa Dupa Fly is monumental by way of influence.  Artists seeing how their creative freedom can pay off as long as they stay true to themselves is a mantra one would hope ALL artists would take heed of & she definitely bet on herself…then successfully conquered.

Edd: We take it for granted now but Missy redefined what it meant to be a female artist. By the late 90s, female rappers fell in two categories – those who flaunted their sexuality and those who presented themselves as tough and rugged as their male counterparts. Missy did both by being herself – never shying away from her sexuality but rocking baggy sweats all the while. Add her dose of interstellar creativity and you had an artist who showed women (both artists and listeners) that they didn’t have to conform to a single box. That’s Supa Dupa Fly’s legacy – there are no rules.

Is this Missy’s best work?

Deland: Absolutely…hands down!!  Not that she didn’t have OTHER hot albums aside from this, but those albums wouldn’t have gotten the listens they did if THIS album didn’t set the platform that displayed Missy’s “to the left” version of Hip-Hop/R&B that she created.  And it gets no clearer that on this album…a mere CLASSIC!!!

Edd: Remember what I said earlier about the obvious answer being the right choice? WELLLLL, not in this case. Supa Dupa Fly is Missy’s most defining album, the one that will always be her signature release. I also believe it’s an undisputed classic, due to its groundbreaking production, consistent quality and lasting influence 25 years later. And, if I haven’t brought it up enough, it’s my favorite album from my favorite artist. That said, I have to be the Unbiased Reviewer you hate to love and, objectively, I recognize that there are a few weak tracks here. So no, it’s not her best album – in terms of track quality and overall consistency, that goes to 2002’s Under Construction, an album she still hasn’t topped. But my heart will always be with Supa Dupa Fly.

Who got it right, Deland or Edd? Let us know below and help us celebrate Missy.