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‘Da Real World’: When Missy Elliott Ruled The Planet
Warner Music
In Depth

‘Da Real World’: When Missy Elliott Ruled The Planet

Deepening her vision on a collection of dark-hued hip-hop cuts, Missy Elliott straddled the globe with her second album, ‘Da Real World’.


“For this album I wrote a lot of catchy hooks,” Missy Elliott said in 1999, of her second album, Da Real World. “They’re hot, but they’re simple.”

Following on from her phenomenally inventive debut, Supa Dupa Fly, Da Real World had to land a sharp Missy-is-back blow, instantly proving that this new album would not loiter in the shadows of her prodigious debut. It did all that, and more. On Da Real World Elliott moved from the Technicolor surrealism of Supa Dupa Fly into darker waters, yet always with that trademark Missy-ness of intellect, flamboyance and futurism. “I named my album Da Real World because I talk about real, real, real topics,” she said.

Listen to ‘Da Real World’ here.

When did Da Real World come out?

Da Real World came out on 22 June 1999 and was developed at a time when Elliott was feeling the pressure to come up with a successful follow-up to 1997’s genre-warping Supa Dupa Fly. “It’s really hard, the sophomore album,” she told MTV. “You try not to get that sophomore jinx.” Early efforts proved fruitless, so she took a step back; consciously avoiding thinking of the songs as being for her second album, she instead tried to treat them as if she were recording another artist.

Ultimately, Elliott’s experience helped her overcome her fears. After all, she was no debutante. Although it had felt as though Supa Dupa Fly was a starbeam burst onto the scene, it was in fact the product of a long backroom history. With her very close collaborator Timbaland (who has compared their bond to that of an “old married couple”), Elliott had cut her teeth crafting 90s R&B – notably through writing and producing Aaliyah. Elliott’s production work, as well as her exceptional writing and rapping, is still an underappreciated aspect of her career.

Who wrote the songs on ‘Da Real World’?

Most of the songs on Da Real World were written by Elliott and her collaborator Timbaland, occasionally with guests, such as Lil’ Kim and Eminem, contributing their own raps. Elliott’s penchant for inventing words and weirding-up clichés is obvious from the very outset, with Beat Biters rhyming “boobetti” with “confetti”, and Elliott threatening to “burn a whole club down like I was Carrie”.

“This is an album for the females,” Elliott said in 1999 of Da Real World. “It’s a build-a-self-esteem album, ​’cause it’s still a male-dominated world… And I feel like it’s time for us to get our own, set our own boundaries and goals.”

What singles were from ‘Da Real World’?

The first single from Da Real World was She’s A Bitch: a pure statement of defiance. “You don’t hear people call males ‘bitches’,” Elliott said in 1999. “But I’ve heard that people talk that way about Chaka Khan. And Aretha Franklin.” Elliott instead wore the word like a searing red letter: if being a bitch meant being a confident, strong woman threatening male egos, then she was it, and she was going to rap about it. Bald, beautiful and majestic in the sleek music video, she strides the words like a colossus.

All N My Grill, featuring Big Boi (from OutKast) and Nicole Wray, was the second single from the album. Wray had also appeared on Supa Dupa Fly, and had been closely associated with Elliott since the age of 16. Elliott had felt the teenager, who was then living in extreme hard times within a violent neighbourhood, evoked Mary J Blige. “I made it out of that concrete jungle,” Wray later reflected. “Missy gave me the opportunity.” A second version of All N My Grill, with MC Solaar rapping in French, was also released as a single in Europe.

The third and final Da Real World single was a remix of Hot Boyz, featuring Lil’ Mo, Nas, Eve and Q-Tip. This single was particularly significant – and not just because it was an enormous hit, breaking the record for most weeks at No.1 on both the US R&B and Hot Rap Singles charts. Hot Boyz leaned into a more club-friendly sound, which Elliott would explore more fully on her next album, Miss E… So Addictive.

Who were the guest stars on ‘Da Real World’?

Da Real World featured some of the music industry’s most intriguing new artists, and also gave scope for established stars to try out different avenues. Lil’ Kim, featured on two interludes (Checkin’ For You and Throw Your Hands Up) is even tougher than she had been on her debut album, Hard Core. Her raps are early portents of the vibrant frustration she would channel so ferociously on 2005’s The Naked Truth.

In 1999, Beyoncé was still in Destiny’s Child, and her turn on Elliott’s Crazy Feelings is instructive. One of the deepest, starkest R&B cuts on Da Real World, it sees the future “Queen Bey” step beyond her Destiny’s Child image. She would also feature on Elliott’s Under Construction track Nothing Out There For Me, for which Elliott convinced her to rap. “She was like: ‘Miss, if I sound crazy, don’t put this out!’” Elliott said in 2019. “And I said: ‘Trust me, B, I’m not gonna allow you to sound crazy.’ She went in there and now she’s rapping better than me!”

Elliott also nabbed a feature from the most controversial rap artist of the time, Eminem, who appears on Busa Rhyme. “He hadn’t even came out with My Name Is yet,” Elliott said in 1999. “I heard something of his and instantly told Tim[baland], ‘I need this guy on my album.’ Immediately when I heard him rap, I thought, He’s special.” Slim Shady’s vicious women-hating persona (specifically shouting out that he hates “bitches”) is more than matched by Elliott’s vehement pissed-off-ness in a cut-up, scratchy, barrier- and button-pushing track.

What did Missy Elliott do next?

The next album Missy Elliott released was Miss E… So Addictive, a very different work that enveloped Elliott’s rap skills within club beats, R&B grooves and pop anthems. Da Real World is an intense listening experience and, with its follow-up, it seemed Elliott wished to shut that real world out a bit more, finding solace in joy instead.

But for Da Real World, she was determined to open eyes and start confrontations. “We gotta start tapping into what’s really going on,” she said in 1999. “We’ll lose our minds if we try to think, when it’s rainy outside, when we go outside, it’s sunny.”

Find out where Missy Elliott ranks among the best female rappers of all time.

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