The 1999 Grammys were billed at the time as the “”Diva, celebrating the industry’s female icons past and present.
The decade’s twin titans, Whitney Huston and , sat the night out, but the belting style they helped popularize was everywhere.
There was Céline Dion, one of the night’s big winners, picking up well-earned record of the year, song of the year and best female pop vocalist honors for “My Heart Will Go On.” An old-school ballad, the song was also an old-school hit – it sold 15 million copies, a figure only matched in the iTunes era by the Black Eyed Peas’s “I Gotta Feeling.”
The night’s other winner (and official recipient of the ‘99 Grammy’s “”Belly) was ex-Fugee Lauryn Hill, who took home five trophies: album of the year, best female R&B vocal performance, best R&B album, best rhythm & blues song and best new artist. For the Grammy voters, Hill looked like the future: a smart, soulful diva who could also rap. Hip-hop, it seemed, finally had its Whitney Houston, or maybe its Alanis Morissette.
Speaking of Alanis, the former Jagged Little Pill was on hand after her four-trophy barnstorming three years prior to validate the Grammys’ faith in her. She performed a masterful “Uninvited,” and won two Grammys for the song to boot.
Rounding out the women of the year were a series of next-generation country divas. The Dixie Chicks won for best country album and best country performance by a duo or group, but even they had to kneel before the raw power of Shania Twain. The woman who owned pop radio the previous year took home two trophies for “You’re Still the One,” and she topped off her night with a spirited rendition of “”Man!
Even the divas of old got in on the fun. After being essentially shut out for the first 15 years of her career, Ray of Light-era Madonna picked up a pair of Grammys and put on a geisha-themed version of “Nothing Really Matters” that probably wouldn’t fly today.
Other bets on the future made by the 41st Grammys committee: the late-’90s wave of Latin music. Above, watch Ricky Martin tear the house down with his leather-pants-assisted performance of “The Cup of Life.”
Another totally 1999 moment: Will Smith’s all-leather ensemble, seen here helping the Fresh Prince celebrate the award for best rap solo performance for “Gettin’ Jiggy Wit It” – (over Jay Z’s “Hard Knock Life”!)
Still, the presence of BSB meant that viewers were also treated to a classic Aaron Carter appearance. But Nick’s little bro’s flashy yellow suit would not be the best outfit of the night. No, that honor would go to
Fat Joe and Big Pun, for their matching (but not too matchy-matchy) ensembles.
15 years, everybody. 15 years.
Can’t get enough of Red Carpet Season? Be one of the first to get the news from all the awards shows! Sign up below for our daily newsletter – so you’ll be the first to know all about the winners, the best speeches and the most fabulous fashion.