Date: February 24, 1999

The Moment: At the 1999 Grammys, former Fugees member Lauryn Hill's first solo effort—the commercial and critical smash hit The Miseducation of Lauryn Hill—was nominated 10 times, and won five of those awards: Best New Artist, Best R&B Song, Best Female R&B Vocal Performance, Best R&B Album, and Album of the Year, which was most notable, as it was the first rap album to win the award.

The Impact: Hill's Grammy sweep was seen as one of the more accurate, fair, and generally correct moments of the Grammy voting committee. The wins put her on the map to an entire contingent of music listeners who hadn't already heard her album, mostly made up of people who didn't regularly listen to rap or R&B. Sales of the album skyrocketed, and it went on to sell 19 million copies worldwide.

The Upshot: The year after, Hill won an Album of the Year Grammy for her co-production of Santana's star-studded Supernatural, making her the only female artist to win this prestigious award twice consecutively. In February 2001, she settled a 1998 lawsuit with artists who she'd failed to properly credit on Miseducation, reportedly paying $5 million.

Disliking what she felt success had done to her life and psychology, Hill went into seclusion following Miseducation's outsized success, and didn't release another album until an emotional solo performance on MTV Unplugged 2.0. She's since dabbled with a short-lived Fugees reunion, songwriting, and strings of live appearances here and there, but nothing even remotely resembling the worldwide acclaim (and thus, attention) she received after the Grammys.