Chart Rewind [Hot 100]: TLC’s ‘Unpretty’ Hit #1 This Week in 1999

Published: Friday 18th Sep 2020 by Rashad

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

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

This week we’ll tracking back to TLC‘s fourth and final #1 hit, 1999’s ‘Unpretty.’

Despite the enduring success of their blockbuster comeback single, 1999’s ‘No Scrubs,’ R&B trio TLC didn’t wait before its steam cooled to generate a release date for the bop’s follow-up single, ‘Unpretty.’

Reportedly conceived and written by the group’s lead singer T-Boz after witnessing women get berated for their appearances on a talk show, appointing the uplifting song’s as ‘Scrubs’ successor may have also served as a strategic move given the criticism launched its way for being ‘man-bashing.’

Making a handsome #76 premiere on the Billboard Hot 100 in late June 1999 (which ‘No Scrubs’ was still in the top 5), ‘Unpretty’ was penciled in the chart’s top spot not even three months later thanks to its touching Paul Hunter-directed music video.  Deeply personal in that it shed light on some of the group member’s own insecurities, the visual was lauded for its head-on tackle of issues related to mental health, self-esteem, body shaming, eating disorders, and so much more.

Owning the chart for 3 weeks, the reign would be the last time TLC touched the top of the Billboard Hot 100.

When the dust settled, ‘Unpretty’ was not only nominated for Song of the Year and Best Pop Performance by a Duo or Group with Vocal at the 2000 Grammy Awards, but it was eventually certified GOLD by the RIAA (denoting sales of over 500,000 in the United States) and helped push its parent album, ‘FanMail,’ to worldwide sales of over 10 million.

**Related:  Click here to read our TGJ Replay to the ‘FanMail’ album**

Look below to who joined TLC in the top 25 on this week’s Chart Rewind:

Hot 100 This Week in 1999


Hot 100 This Week


Click here to read this week’s full ‘Hot 100 chart check.’

Your thoughts?

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  1. Clarks0o0ñ September 18, 2020

    One of their best songs

    But their vocals and production on this song sound weird. Like they used cheap equipment to record the song.

    Remember when usher and chilli wear a hit couple. Lol good ole days

    • 1988 September 19, 2020

      “Unpretty” brings warmth to FanMail and their vocal production reflected that. It’s a masterpiece of a song that helped innovate R&B/Pop radio. “Unpretty” has sing-a-long, radio-friendly qualities and the laugh that T-Boz makes at the end was done to show they were having fun in the midst of a very important message to women (and men alike). I’m currently writing a FanMail review off and on so some of this are my notes. 🙂

  2. Zion September 18, 2020

    UNPRETTY >>>>>>>> Destiny’s childrens whole discography

    • Don’t touch my hair September 19, 2020

      Lol stop

  3. #WAP September 18, 2020

    Icons. Legends. Destiny’s child could never

    • 🍭marilyn monh-O-E🍭(da one & only) September 18, 2020

      Destiny’s child did and outdid these vocally-challenged ladies. But I do love this song tho. 💁🏼‍♀️💁🏼‍♀️

    • So FRESH September 18, 2020

      …but it’s obvious and clear DC “more than could ever”! The staying power and longevity the group has and how ppl freak out when they’re together proves that! Not to mention they have HUGE RECORDS too.

      I still love TLC and this song too. This ERA was bomb.

  4. Liamjaim September 18, 2020

    i love it.

  5. eric September 18, 2020

    One of my favorites from TLC. So many great songs on that chart. Music will never be the same.

  6. J September 19, 2020

    TRL was lit back then lol. Best childhood ever 😪

    • IAMME September 19, 2020


  7. Don’t touch my hair September 19, 2020

    Best Selling Female Group of All Time Worldwide:

    1. Spice Gurls
    2. TLC
    3. Destiny’s Child
    4. PussyCat Dolls
    5. En Vogue

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