📺 MTV VMAs • 1999 27 YEARS AGO… Now THIS was VMA glamour. Janet Jackson arrived at the 1999 MTV Video Music Awards during the tail end of The Velvet Rope era looking absolutely flawless. The hair, the diamonds, the smoky purple eye, the deep navy gown. Elegant, sexy, and effortlessly late-’90s Janet. And she wasn’t exactly showing up as background decoration. That year Janet was linked musically with Busta Rhymes through the spectacularly expensive Hype Williams sci-fi masterpiece “What’s It Gonna Be?!” The video received four VMA nominations: Best Hip-Hop Video Best Direction Best Art Direction Best Special Effects It won none of them, which is one of those award-show decisions that has aged rather strangely considering people are still talking about that video decades later. Awards shows do occasionally manage to lose an argument with history. Janet also presented Best Dance Video, handing the Moonman to Ricky Martin for “Livin’ la Vida Loca.” And contemporary Janet chronology records her attending the ceremony with Q-Tip, adding another little snapshot to that fascinating late-Velvet Rope period before she disappeared into the studio and eventually emerged with All for You. The 1999 VMAs were held September 9 at New York’s Metropolitan Opera House, during that ridiculous period when MTV could put Janet, Madonna, Lauryn Hill, Britney, TLC, Ricky Martin, Eminem, Jay-Z and half the music industry under one roof and somehow make it feel normal. September 9, 1999. Janet Jackson. Peak MTV. Peak pop culture.