In Party Like It’s 1999, I’m marking my birthday June 25th by reviewing every Billboard Hot 100 #1 hit from my birth year 1999 along with other notable hits from the year.

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TLC- “Unpretty”

HIT #1: September 18, 1999

STAYED AT #1: 3 weeks

These days, we’re used to hearing bland and corporatized empowerment songs that are lacking any emotion or resonance that it’s become easy to dismiss all empowerment songs as soulless schlock. That’s a shame as empowerment songs, when done right, does make for pretty effective music especially toward the people it’s aimed at. After all, we live in a society that prioritizes certain looks over others so some people aren’t going to feel like they fit in with what society dictates. That was true in 1999 when R&B group TLC made “Unpretty,” their fourth and final #1 hit, a song written from real life insecurity that manages to be an effective anthem to women of not having to change themselves to please others.

“Unpretty” began life as a poem member T-Boz wrote after getting out of the hospital recovering from sickle-cell anemia. Her boyfriend wasn’t around much making her feel emotionally insecure which served as a major inspiration along with watching an episode of the talk show Ricki Lake and seeing men call women fat pigs. After her recovery, T-Boz shared her poem with Dallas Austin, the songwriter and producer behind the group’s first #1 “Creep,” who liked it enough to write a whole song around it. T-Boz would eventually release her poem along with others in her book Thoughts.

Austin was inspired by the title for its music and lyrics as he said to Fred Bronson in Billboard Book of No. 1 Hits, “Once I saw the title, I went to my keyboard and guitar and started playing melodies that would compliment it. I didn’t want it to be aggressive. I wanted it to be friendly—for a song called “Unpretty” talking about how much you don’t like yourself—so the message would come across to people with those kinds of problems or issues. I thought it would be unique to get it across in a sweet way.” Austin further mentioned being inspired by the alternative pop of acts of the time like Natalie Imbruglia and incorporating many of those elements into “Unpretty.”

“Unpretty” was the second single released off of TLC’s FanMail after “No Scrubs” and introduced a new lane for the group. They had already made their image doing songs about female independence and societal problems but never released a full-on empowerment anthem. In the song, the members sing about feeling insecure and having to go through various cosmetic changed to please the men they are with. It’s obviously a very prominent issue for many girls in our society and TLC sing to them to look at their beauty within and that they don’t need to change their appearance to please others if it makes them uncomfortable. This song isn’t TLC’s all-time best performance but like with “No Scrubs” you definitely buy them telling women to look inside and appreciate their true beauty. 

Austin’s production gives the song a genre-free zone where R&B, alternative, and pop all intersect. Nice fluttery guitars and drum beats give the song a pretty feel that compliments the subject matter of the lyrics lending. There are also cool little hints of guitar solos that raise it for me. Anyone who’s felt insecure about their beauty can listen to “Unpretty” and feel empowered. The song through its music is uplifting enlightenment for those struggling with insecurity over their bodies and beauty which goes along with what Austin said about making the song sound friendly. It gets the job done. Despite that, the song doesn’t exactly hold up to repeated listens for me. It’s not because I’m not in the intended audience for the song but it just breezes by without leaving too much of an impact. It’s a song that immediately blends into the background which is my issue with a lot of these alternative pop songs of the late ‘90s.

The video for “Unpretty,” directed by Paul Hunter helps to drive home the song’s message. In it, we see the members of TLC singing in what looks like a Buddhist temple lair as well as a colorful meadow with butterflies and ladybugs. This is all presented next to storylines like a young girl exhibiting bulimia to look more skinny like what she sees in the magazines and Chili getting breast implants to make her breasts larger in order to please her boyfriend. Toward the end, we see Chili bailing out of the surgery at the last minute and the young girl tearing down posters of skinny models from her bedroom wall accepting her body. 

“Unpretty” hasn’t exactly lingered in the cultural memory as TLC’s other hits like “No Scrubs” or even “Waterfalls” has but it has made an impact nonetheless. Austin remembers getting letters from kids with cancer and other illnesses citing the song as a major help in changing their perspectives. T-Boz recalls Lady Gaga crying saying to her that “Unpretty” changed her life as a kid being an outcast. It’s done a lot of good in the world. 

TLC wouldn’t get back to #1 after “Unpretty.” They’re a quintessentially ‘90s act and would get back into the Top 10 after 1999. The success of FanMail wasn’t enough to quiet tensions in the group specifically with Left Eye who expressed frustration over her treatment in the group. She challenged her bandmates to record solo albums but it was eventually canceled. Left Eye did have a solo hit soon after with her guest feature on Donell Jones’ 2000 R&B hit “U Know What’s Up” which peaked at #7. (It’s a 6.) The group began recording a new album in 2001 while Left Eye recorded a solo album named Supernova which initially was released overseas but Arista Records scrapped its release in America. Left Eye soon began working on a second album but before it was completed she died tragically in a car accident in Honduras in April 2002 at age 30.

Soon after, the surviving members decided to retire after the next album release 3D which did moderately well upon its release in November 2002 but was certainly a big fall from the heights of CrazySexyCool and FanMail. The retirement didn’t last long as T-Boz and Chili decided to carry on TLC as a duo without a replacement for Left Eye. They did a reality show where singers auditioned to sing on a TLC song. Since then, TLC has shifted into a nostalgic act continuing to tour often paired with other ‘90s acts like New Kids on the Block, Naughty By Nature, All-4-One, and C + C Music Factory. They released their fifth self-titled album in 2017 with the help of donations through a Kickstarter campaign. Both T-Boz and Chili say it’s their final album but plan on continuing to tour in the TLC name.

GRADE: 7/10

BONUS BEATS: Here’s Dianna Argon and Lea Michele covering “Unpretty” along with “I Feel Pretty” from West Side Story on a 2011 episode of Glee:

(The Glee cast’s highest-charting single is their 2009 version of Journey’s “Don’t Stop Believin’,” which peaked at #4. It’s a 5.)

BONUS BONUS BEATS: Here’s prior The Ones of the ’10s subject Kelly Clarkson covering “Unpretty” today for her Kellyoke series: