Missy Elliott Reveals Her ‘Most Stressful Album’

Missy Elliott’s second album, Da Real World, produced major hits like “She’s a Bitch,” “All N My Grill,” and “Hot Boyz (Remix),” but it also marked one of the most challenging periods of her career. In an interview with Variety published on Monday (June 17), Elliott shared her reflections on the 1999 album ahead of its 25th anniversary on June 22, detailing the intense pressure she faced during its creation.

“That album was stressful,” Elliott confessed. “It was my most stressful album. I appreciated it later, but if you know anything about the periods of albums and the second album, we call it the sophomore jinx. Especially if you have a successful first album, you are stressed out because you’re chasing trying to be that first album.”

Elliott’s debut, Supa Dupa Fly, set high expectations, and she felt the pressure to surpass it. “That first album was successful for me, so I was trying to find something that was going to be bigger than ‘The Rain,’ both visually and sonically. Years later, I look back on that and realize it was one of the most creative periods because it was theatrics mixed in with Hip Hop. If you listen to a lot of the songs, there’s a lot of strings—not dark strings, but very theatrical, very dramatic.”

The stress of the sophomore jinx forced Elliott into a unique creative zone. “Everything was very dramatic. I can appreciate that album as one of my tops because, at the time, it was stressful. But when I look back, I’m like, damn, we were in 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.”

Earlier this year, Elliott delighted fans with a nostalgic trip on Instagram, showcasing some of her iconic outfits from her prime. “Yooooo so I found all my ORIGINAL outfits I wore in some of my most ICONIC videos & I decided to see what I would look like in these fits in the year 2024,” she wrote. “I went back in time WOW. Father, I thank you! I’ve come a long way!”

The Instagram clip featured throwbacks to music videos like “The Rain” (1997), “Hot Boyz” (1999), “Sock it To Me” (1997), “Beep Me 911” (1998), and “Gossip Folks” (2002), reminding fans of Elliott’s enduring influence and unique style.