Readers of That Grape Juice know what avid music lovers we are – especially of hits past.

So, as our retrospective segments, ‘From the Vault’ and ‘TGJ Replay,’  allow us the chance to re-spin the gems and jams of yesterday of one artist, our latest feature –  Chart Rewind – serves as a variation of our Retro Rewind assay to salute an entire era of music history.

This week we’d really love to replay ‘Doesn’t Really Matter’ – Janet Jackson‘s first #1 hit of the millennium.

Join us inside:

As Janet fans entered the new millennium, they undoubtedly not only questioned where the Pop diva would fit in the music industry’s shifting climate (which was increasingly favoring Teen Pop and Hip Hop) but also how she would follow the mega-successes of her two studio efforts of the 90’s – the 6x Platinum ‘Janet.’ album and the 3x Platinum ‘Velvet Rope’ LP.

While hard at work on her 7th studio production (‘Rope’s follow-up), the youngest of the Jackson clan was also flexing her acting muscle as she’d been cast as the love interest in ‘Nutty Professor II’ – the successor to Eddie Murphy‘s wildly successful 1996 comedy film, ‘The Nutty Professor.’

It would only make sense that having an act of Jackson’s musical caliber in the movie would call for her to contribute to its accompanying soundtrack, especially given the last time she lent her songwriting pen to music for a motion picture she nabbed an Academy Award nod for the endeavor (see: ‘Again’ from 1993’s ‘Poetic Justice’).  To no surprise, her contribution – much like with ‘Justice’ – yielded a smash hit.

Co-written with longtime collaborators Jimmy Jam and Terry Lewis, the trio crafted ‘Doesn’t Really Matter’ – an uptempo Pop tune housing lyrics that essentially mirrored the mindset of Jackson’s character in ‘Professor.’  A sonic foretaste of what was set to come on ‘Rope’s follow-up (later titled ‘All For You’), ‘Doesn’t Really Matter’ – released in May 2000 – impacted the Hot 100 on airplay alone and debuted within its top 60.  By this week that year, the tune had climbed to #1 on the tally and stayed there for 3 weeks.

Coming as the 9th #1 hit of her career, the achievement penciled her in history books for becoming the first female act with a Hot 100 chart-topper in three consecutive decades (1980s, 1990s, 2000s) and made her the first artist overall to have chart-toppers in each of those specific decades.

When the dust settled, ‘Doesn’t’ didn’t get any love from the Recording Academy as it garnered no GRAMMY nods but it did take home Gold elsewhere:  the RIAA.

Look below to see who joined her in the top 25 this week 20 years ago:

Hot 100 This Week in 2000

Hot 100 This Week

Click here to see this week’s fully updated ‘TGJ Chart Check: Hot 100’ edition.

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