The 2019 Grammys

Rewinding the Charts: 15 Years Ago, Janet Jackson Scored a Hot 100 First

Christina Radish/Redferns
Janet Jackson

On Aug. 26, 2000, Jackson became the first artist to notch Hot 100 No. 1s in the '80s, '90s and '00s with 'Doesn't Really Matter.'

ON AUG. 26, 2000, JANET Jackson claimed her ninth No. 1 single on the Billboard Hot 100 with "Doesn't Really Matter" and became the first artist to summit the chart in the '80s, '90s and '00s, with a brand of street pop that was sexually confident and socially aware. (Madonna would match the feat just three weeks later when "Music" knocked Jackson from the top spot.)

"Matter" was released from the soundtrack to Nutty Professor II: The Klumps, co-starring Jackson and Eddie Murphy. Then 34, the youngest of the musically talented Jackson children had wrapped the '90s with 18 top 10 Hot 100 hits, second only to Mariah Carey's 19.

Following the success of "Matter," Jackson scored another No. 1 single in 2001 with "All for You," but her momentum came to a halt on Feb. 1, 2004 when, during a halftime performance at Super Bowl XXXVIII, Justin Timberlake tore open Jackson's costume, exposing one of her breasts to 140 million TV viewers. The infamous "wardrobe malfunction" led to a media firestorm and FCC investigation, and Jackson hasn't cracked the top 10 of the Hot 100 since. She did, however, top the Billboard 200 in 2008 with her album Discipline.

Ask Billboard: Janet Jackson's Biggest Billboard Hits

At the conclusion of a 2011 tour, Jackson stepped away from the spotlight and married billionaire businessman Wissam Al Mana in 2012. In June, she re-emerged to announce an upcoming world tour and a new album (its title has yet to be announced), her first studio recording in seven years. Lead single "No Sleeep" returned Jackson to the Hot 100 for the first time since 2008, marking her 40th chart hit. The sensual track also topped the Aug. 22 Adult R&B Songs airplay chart, becoming her first leader on the list in 17 years.

A version of this article first appeared in the Aug. 29 issue of Billboard magazine.