1999 Rewind: Remembering Missy Elliott’s Da Real World

Are y’all ready to party like it’s 1999? We all love the 90s here at Soul In Stereo, so it’s only right to revisit albums that are marking 25 years in 2024. 1999 Rewind looks back at all your old faves and see how well they hold up.

I’ve been waiting for this one! In 1999, my hometown homie Missy Elliott delivered her long-awaited sophomore album, and it proved to be quite the departure from her debut. What did we think about it at the time, and how well has it aged? I had to invite my album review understudy Brandon O’Sullivan of Shatter the Standards – AKA Theo – for this look back at one of the most important artists of our generation.

OK, let’s flash back to 1999. What were your first thoughts of this album?

Brandon: I didn’t listen to Da Real World by Missy Elliott when it came out in 1999 since I was just four months old. But when I did hear it years later, I was blown away. The beats and production grabbed my attention right away. I found the rhythm infectious and the delivery sharp. The mix of sounds was unlike anything I’d heard before. Missy Elliott’s style felt fresh and unique. It made me appreciate the creativity put into making music.

Edd: That man said he was four … months … old. Excuse me, I have to go change my adult diaper. Anyway, it probably goes without saying that Da Real World was my most anticipated album drop of 1999. Missy Elliott’s 97 debut had essentially cemented her as my favorite artist – and she still wears that crown today – and I couldn’t wait to hear the follow up. 

However, I must be honest, my immediate action to the album was that of slight indifference. Obviously I didn’t hate it – I liked it a lot, especially the singles. But the dark, more mature production was such a jarring departure from the light-hearted futurism of her debut, like going from colorful Mega Man vibes to conference calls with Darth Vader. It took a long time for me to appreciate Missy and Timbo’s vision, but eventually I did and it has since become a fave.

Let’s talk best song!

Brandon: “She’s a B****”

“She’s a B****” stands out as the best track on the album. The song has a hard-hitting beat that grabs attention right away. Missy’s confident delivery really shines through the bold lyrics. The production by Timbaland is top-notch, creating a dark and moody vibe. It’s a track that feels timeless and ahead of its time. The hook is catchy, and the verses flow perfectly. Overall, it encapsulates the strong, fearless attitude that Missy is known for.

Edd: “She’s a B****”

I might not have loved Da Real World on my first listen, but I had no trouble falling for “She’s a B****.” I remember Missy going on one of the music video shows – probably MTV – to explain that this wasn’t a diss song directed at an enemy, instead she was reclaiming the Dreaded B Word for herself. This was women’s empowerment on an intergalactic level. Everything from her katana-sharp delivery to the foreboding production made this a moment.

What’s your pick for best video?

Brandon: “She’s a B****”

The video for “She’s a B****” is a visual feast. Director Hype Williams creates a futuristic, dystopian world that perfectly matches the song’s aggressive energy. The choreography is sharp, and the editing is rapid-fire, making for a video that’s impossible to look away from. It’s full of futuristic and striking imagery. Missy’s fashion choices and the special effects make it memorable. The black latex outfits and underwater scenes are just a few highlights. Each frame feels like a piece of art, taking music videos to a new level. The visual storytelling keeps viewers hooked from start to finish. No wonder it remains iconic even years later.

Edd: “She’s a B****”

Missy may be a master of music videos but, overall, the visuals for this project weren’t as memorable as those from her previous album, nor the albums to come – with one exception, of course. “She’s a B****” did not disappoint. Missy rising from the depths of that monochrome water rocking a baldie was shocking, the perfect compliment to the otherworldly production. Missy was like Sith Lord meets Mad Max (Mad Maxine?). It’s a stunning display of visual artistry.

Which album cut should have been a single?

Brandon: “Crazy Feelings”

This track had all the makings of a hit single. The combination of Missy and Beyoncé’s vocals surprisingly mesh well here. The catchy, sing-along hook and the relatable lyrics about catching feelings would have resonated with a wide audience. It’s a shame this track wasn’t given the single treatment it deserved.

Edd: “Smooth Chick”

I’d love to go with “You Don’t Know,” the most underrated song on the project. You can’t tell me that a Jerry Springer-styled video with Missy and Lil Mo at each other’s throats wouldn’t have been fire. 1999 was the prime era for afternoon brawls on daytime TV, after all. But nah, the best option for a single would be “Smooth Chick.” Those funky horns and that slick production could have done damage in the clubs and on the airwaves. I’m sure Hype Williams could have cooked up a Speed Racer- esque video to accompany it as well.  Anime Missy would have been fun.

Hot Boyz Remix vs. Hot Boyz Original Recipe – which do you prefer?

Brandon: “Hot Boyz Remix”

The “Hot Boyz Remix” easily surpasses the original. The all-star lineup of guest MCs brings fresh energy. Also, shout out to the remix video, as it was a star-studded affair featuring appearances from Nas, Eve (who stole the show), Q-Tip, and Lil’ Mo. The futuristic, neon-drenched visuals are quintessential Hype Williams and showcase Missy’s avant-garde style.

Edd: “Hot Boyz Remix”

This may be surprising to some of y’all but I don’t revisit “Hot Boyz” all that much during my binges of this album. That might be a different story if we had access to the remix on the LP. The original is solid but bringing in that squad of A-listers to assist Mo really elevates the song. And yes, Eve killed her verse.

Who delivered the best feature on the album?

Brandon: Beyoncé

There are some features you can choose from. The hip-hop in me would’ve said Eminem, but that would be easy (although Gina Thompson’s ad-lib delivers every time), or Lil’ Mo if she’s credited on “Hot Boyz.” However, I will give it to Beyoncé, and her voice in the song “Crazy Feelings” complements Missy’s style perfectly. It’s interesting to see the blend of different talents come together. A month later, they would return on DC’s The Writing’s On the Wall.

Edd: Lil Mo

Gotta go with Lil Mo, she’s the MVP of this project. She not only held down “Hot Boyz,” but played the perfect foil to Missy on “You Don’t Know,” going to war with her on the R&B AND rap battlefields on the same track. Mo is so talented and she doesn’t get enough credit.

A Timbaland/Missy project always has outstanding production. Which song stood tallest?

Brandon: “She’s a B****”

The production of “She’s a Bitch” by Timbaland is unmatched. The beat is like nothing else, featuring a mix of futuristic sounds and hard-hitting drums. Timbaland’s knack for creating unique soundscapes shines brightly here. The use of space and rhythm keeps listeners hooked. The production complements Missy’s bold lyrics perfectly. Every element in the track feels meticulously crafted. It’s a production masterclass that stands the test of time.

Edd: “She’s a B****”

“She’s a B****” runs away with this one. It’s the evolution of everything great about Timbaland’s now-iconic production of Aaliyah’s One in a Million,” except more menacing. The greatest strength of the early Timbaland production run is his willingness to take risks. The result was music that still sounds decades ahead of its time 25 years later.

The sound of Da Real World was much darker than the previous album Supa Dupa Fly. Does the change in direction work?

Brandon: While Supa Dupa Fly is exuberant and playful, Da Real World finds Missy exploring darker, edgier territory. Timbaland’s beefed-up beats are more aggressive, and Missy’s rhymes are razor-sharp. It may not hit on the first listen, but it showcases Missy’s versatility and willingness to take risks. The moodier beats and themes feel fresh and less mainstream. The sonic shift is a risk that pays off, proving her artistic versatility. Speaking of Timbo, you have to put in perspective from Jam & Lewis to Darkchild to She’kspere; they were largely eating off his style/sound since he came into the scene, thanks to Aaliyah’s One In a Million. It’s a bold move that pays off, highlighting her dynamic range.

Edd: With the benefit of hindsight, yes, this was a move that payed off. The production was a reflection of the album’s more mature tone. Remember, “She’s a B****” wasn’t just the lead single, it was supposed to be the name of the album before Missy was talked down. Had you asked me in 1999, I wouldn’t be as confident in her change in direction.  The initial singles were all over TV but kinda struggled on radio before “Hot Boyz” finally took off in the 11^th hour. But, as always, Missy proved to be well ahead of the curve, as her journey down dark futurism would lead to greater acclaim and appreciation in later years. It was a big ol risk, but the reward was worth it.

Is Da Real World overrated, underrated, or properly rated?

Brandon: We often discuss her debut, Miss E, and even Under Construction to a degree, but Da Real World is criminally underrated. It doesn’t get as much recognition as her other albums, which is a shame because it’s cohesive and sonically adventurous. Missy’s songwriting is still intact, and the featured artists (for the most part) bring their A-game. Despite its brilliance, it often gets overshadowed by her other works. It’s an album that deserves more love and attention.

Edd: This is tough. Most of Missy’s projects range from great to awesome, and most of them have their share of fans. But Theo is correct – Da Real World often is lost in the shuffle of early Missy albums. It lacks the big singles of Miss E … So Addictive and Under Construction, and doesn’t have the landmark legacy of the debut. But as I mentioned above, in recent years I’ve seen a stronger outpouring of love for this project, and Missy has been vocal about how happy she was with the final result. I’ll say it’s slightly underrated, but more people are waking up to its greatness. Add me to that list.

Is Da Real World Missy’s best album?

Brandon: While Da Real World is a very good album, it’s not Missy’s best. That honor goes to either her debut Supa Dupa Fly or 2002’s Under Construction. Supa Dupa Fly was a game-changer, introducing Missy’s unique blend of rap, R&B, and pop to the world. Under Construction, on the other hand, found Missy at the peak of her powers, delivering hit after hit. Da Real World is a solid project that showcases Missy’s growth as an artist, with darker, edgier production and sharp writing. However, it lacks the immediacy of her best works. Still, “Hot Boyz,” “She’s a B****” and “All N My Grill” are classics, and the album remains an important part of Missy’s discography.

Edd: If you ask around, there’s often not a consensus on Missy’s best album. Critics often pick the debut, and it’s easy to see why. It literally changed the game for both production and how women are viewed in hip-hop. More analycal playas like myself and Theo may lean toward Under Construction as her best. It lacks the legacy of Supa Dupa Fly, but, song for song, it’s her most complete release. I’ve even seen some fans ride for the Miss E album, likely due to the “Get UR Freak” On effect. And yes, in recent years, Da Real World has begun to creep up the rankings as well. In my eyes, it’s firmly No. 3, behind Under Construction and Supa Dupa Fly, but its daring production and unapologetic approach to womanhood make it among Missy’s best work. Not THE best, but one I’ve grown to appreciate more and more over the past 20-plus years.

Who got it right? Was Brandon on target or did Edd net the highest score? Let us know below and share your Missy memories too.