Missy Elliott Breaks Down Why Sophomore Album ‘Da Real World’ Ended Up Being Her 'Most Stressful' Record

The 52-year-old rapper recalled the pressure of following up her successful debut, 1997's 'Supa Dupa Fly.'

Missy Elliott performs on stage, smiling and wearing a stylish red studded tracksuit and large hoop earrings, holding a microphone
Candice Ward / Getty Images
Missy Elliott performs on stage, smiling and wearing a stylish red studded tracksuit and large hoop earrings, holding a microphone

Missy Elliott says one of her albums had her especially stressed out.

As she prepares to launch her first headlining tour, the 52-year-old hitmaker reflected on her legacy and catalog of hits with Variety. She told the publication that she felt the pressure while recording her second album, 1999’s Da Real World.

“That album was stressful,” Elliott told Steven J. Horowitz with a laugh. “That was my most stressful album. And I appreciated that album later. It was the most stressful because if you know anything about the periods of albums and the second album, we call it the sophomore jinx, and so especially if you have a successful first album, you are stressed out because you’re chasing trying to be that first album.”

in a moment i’ve waited for my entire life, i interviewed @MissyElliott https://t.co/jxTxc134na

— steven j. horowitz (@speriod) June 17, 2024
Twitter: @speriod

Elliott’s debut album Supa Dupa Fly, featuring the single “The Rain,” arrived in 1997 and was a commercial success. Finding a way to match its success with her sophomore effort was a challenge, but she ultimately persevered. 

“I was trying to find something that was going to be bigger than ‘The Rain,’ visually and sonically. Years later, I look back on that and that was probably one of the most creative [periods] because it was theatrics mixed in with hip-hop,” she continued.

Missy Elliott holds a phone while wearing a white shirt with black tie and netted top; her reflection appears below her

Examples of that creatively fertile, larger-than-life period include songs like “All N My Grill,” which featured dramatic strings, “Dangerous Mouths” featuring Redman, and “She’s a Bitch” with its breakdown.

“I can appreciate that album as one of my tops because at that time, it was stressful but when I look back, I’m like, damn, we were in a pocket, a different kind of pocket that was amazing to blend the two because it was hip-hop but it still had the theatrics to it,” she said.

Elliott also imparted some wisdom to artists working on their second album on social media back in 2022. In a series of tweets, the “Work It” rapper told artists not to be afraid, and to get experimental.

People normally charge for this kind of info but I’m giving this to the artist for FREE now let’s see who will be WISE enough to absorb this knowledge like a sponge and APPLY it to their work!💯 pay ATTENTION I also learned from the GREATS💯 https://t.co/sjXMt3HZyA

— Missy Elliott (@MissyElliott) July 6, 2022
Twitter: @MissyElliott

“Sophomore Albums are a very PIVOTAL time for artist! Here is a gem from MISSY! Your sophomore album be stressful but it’s the BEST ALBUM to EXPERIMENT on! Don’t be AFRAID! Becuz If u play safe you will be BOXED in & its hard to get out because your fans get used to that 1 sound 💯,” she wrote at the time.

Missy added, “People normally charge for this kind of info but I’m giving this to the artist for FREE now let’s see who will be WISE enough to absorb this knowledge like a sponge and APPLY it to their work! 💯 pay ATTENTION I also learned from the GREATS💯”

Cardi B, who happened to sample “She’s A Bitch” for her “Like What (Freestyle)” earlier this year, could also count on her Atlantic Records labelmate for some advice for her highly-anticipated follow-up to 2018’s Invasion of Privacy.

“Absolutely yes it’s the time to experiment,” said Elliott on X in April, in response to a fan’s suggestion that 31-year-old Cardi “win” people back by giving fans what they need.”

Yeup!!! I’m a little nervous… but I don’t care! I’m liking doing things that my ears want to listen to and reflecting the moods I been in. It feels good https://t.co/biXOySSnac

— Cardi B (@iamcardib) April 6, 2024
Twitter: @iamcardib

“Take it from someone who experimented and many others which allowed them to NOT be BOXED in to one sound and style… I can name tons who each of there albums sounded nothing like the one before😉,” Elliott continued.

“Yeup!!! I’m a little nervous… but I don’t care! I’m liking doing things that my ears want to listen to and reflecting the moods I been in. It feels good,” Cardi replied.

Out of This World – The Missy Elliott Experience, with special guests Busta Rhymes, Ciara, and Timbaland, kicks off on July 4 in Vancouver, British Columbia at the Rogers Arena. The trek will visit arenas in major cities, including Los Angeles, Houston, Atlanta, and Brooklyn before wrapping up in Rosemont, Illinois on Aug. 22 at the Allstate Arena. 

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