4 Rap Grammy Award Winners From 1999 We Still Revisit Often

The year was 1999. In just a few short months, a new millennium would be upon us. But while we could all see the changing times coming down the road, that wasn’t yet what music fans were talking about in the moment. No, in 1999, it was all about the standout rap acts that were dominating playlists.

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Here below, we wanted to go back in time and remember four of those performers. Indeed, we wanted to re-examine the 1999 Grammy Awards and highlight four rap Grammy Award winners from the end of the 90s that we still revisit often today.

Lauryn Hill

Lauryn Hill began the 1999 Grammy Awards with the most nominations (10) and she ended the night with the most awards (5). That coup marked the power of her debut solo LP at the time, The Miseducation of Lauryn Hill. Among its many accolades, the record became the first hip-hop LP to garner Album of the Year.

The Beastie Boys

The rapping trio from New York City earned two Grammy Awards at the 1999 show. Both were related to the release of the group’s 1998 album, Hello Nasty. For their efforts, The Beastie Boys took home Best Alternative Music Performance for the album and Best Rap Performance by a Duo or Group for their single from the album, “Intergalactic”.

Will Smith

How many lives has Will Smith lived? Today, of course, he is still recovering from the slap heard around the world, but before his Academy Awards drama, Smith earned the first-ever rap Grammy in 1989. Then he became a famous TV actor and then a coveted movie star. But in 1999, Smith earned yet another Grammy Award for Best Rap Solo Performance for his track, “Gettin’ Jiggy Wit It”.

Jay-Z

Jay-Z is the most accomplished person in rap history. And he added to his long list of accolades and awards in 1999 when he took home the trophy for Best Rap Album. He got the award for his LP, Vol. 2… Hard Knock Life. (This is where you scratch your head and wonder how Grammy categories work, since Lauryn Hill’s album wasn’t nominated for Best Rap Album, yet it won Album of the Year—best not to ask questions).

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