Everyone in the world was preoccupied with nervous projections about the future in the months leading up to Y2K—everyone, that is, except Missy Elliott. She proved she’d been living in the future for years already with the release of her 1999 sophomore album, Da Real World. Two years earlier, in the video for her debut single “The Rain (Supa Dupa Fly),” Hype Williams had trained his signature fish-eye lens on the Virginia rapper as she stunted in a patent-leather trash bag and delivered her simple but punchy lines like she knew exactly how cool she looked. The choreography, the laidback stutter-step flow, the twitchy Timbaland beats: There was simply nothing else like it in the late-’90s hip-hop landscape. But with her second album, Elliott proved she was more than a weirdo with dope costumes—she was a visionary. Da Real World was a trip down the rabbithole of Elliott’s darker side, a cybergoth utopia full of banging Timbaland beats (whose imitators the rapper calls out on the glitched-out “Beat Biters”) and turbo-confident women. Sure, Elliott could more than hang with the guys here, including Eminem and Redman, but the record’s real strength is in girl power: Aaliyah, Da Brat, and Elliott make the ultimate trio on “Stickin’ Chickens,” Lil’ Kim talks smack throughout the album, and on “Hot Boyz”—a song that still sounds like the future—Elliott refuses to accept anything less than the best from a man. Elliott originally intended to call the album She’s A Bitch as a feminist reclamation of the term, a move the world wasn’t nearly ready for in 1999. But that’s Missy Elliott for you—always a couple decades ahead of the game.