In The Number Ones, I’m reviewing every single #1 single in the history of the Billboard Hot 100, starting with the chart’s beginning, in 1958, and working my way up into the present.
The Lilith Fair, Sarah McLachlan’s touring festival, had an enormously successful three-year run at the end of the ’90s, and it probably had a bigger effect on popular music, and on popular culture, than most people were willing to admit at the time. I never went to a Lilith Fair because I got the sense, early on, that it wasn’t for me. The first Lilith Fair lineup seemed to revolve around a certain type, the proverbial white lady with an acoustic guitar playing folk songs in a coffeehouse: McLachlan, Sheryl Crow, Shawn Colvin, Paula Cole, Jewel, Meredith Brooks. (Fiona Apple was on that first tour, but I didn’t yet realize how much I would come to love Fiona Apple.) I saw that lineup, and I was out. I probably made some shitty high-school jokes about it, too. This was my standard teenage-dickhead modus operandi — making fun of the stuff that didn’t cater directly to my interests.
Until my friend Jessica Hopper wrote this oral history a few years ago, I don’t think I’d ever really considered how audacious that first Lilith Fair was. At the time — and probably now, too — the few female artists who were allowed onto rock radio were considered each other’s competition. With Lilith, McLachlan and the other organizers did something about that, turning the traveling ’90s festival into a kind of statement of solidarity. The organizers knew that the first year of the festival was too monochromatic, and they worked to address that in later years. I remember briefly considering going to the second Lilith Fair in 1998 to see Missy Elliott and Liz Phair and Luscious Jackson and Erykah Badu, but I never pulled the trigger. I had this idea in my head of what the Lilith Fair was, and I’d decided that this idea was not where I wanted to be.
In retrospect, that whole Lilith Fair scene brought a lot of attention to a lot of voices who probably never would’ve gotten a chance to shine. Lilith artists like McLachlan, Jewel, and Paula Cole had huge hits in the late ’90s. But the biggest and best hit that reflected the cultural and musical values of the Lilith Fair came from a group that never had anything to do with the festival, one that worked in a whole different arena. In what would prove to be their final big moment as pop stars, TLC came out with an utterly gorgeous acoustic pop song about beauty standards and self-image. That song never reached the same iconic status as past TLC chart-toppers like “Waterfalls” or “No Scrubs,” but it might just be my favorite thing that the group ever did.
“Unpretty” came out of a moment of genuine self-doubt and hardship. During TLC’s pop-chart reign, Tionne “T-Boz” Watkins, the de facto TLC leader who always seemed so unflappably chill, was constantly checking in and out of hospitals, being treated for sickle cell anemia. One day, T-Boz was sitting in a hotel room after a hospital stay. She was feeling low because of her treatments and because her boyfriend had just left her. (She’s never identified the boyfriend in question, but it was probably Jodeci’s Dalvin DeGrate. Dalvin and T-Boz are friends now, but the members of Jodeci did not treat the female R&B stars of the ’90s very well.)
Talking to Billboard years later, T-Boz laid out the scene: “When you get out the hospital, you feel so weak and frail and ugly. I had all these IV marks and bruises everywhere, and I was just really skinny. When he left, I was watching [an episode of] Ricki Lake that night, where these men were calling women fat pigs, so I was already emotional.” T-Boz’s response was to grab a pen and a pad from the hotel-room desk and to write a poem. The poem was called “Unpretty.” (For those keeping score, that means “Unpretty” was the second late-’90s R&B chart-topper written in response to the trashy daytime talk shows of the era, following Brandy and Monica’s Springer-inspired “The Boy Is Mine.”)
At the time, T-Boz was writing a lot of poetry; it was a way for her to cope with everything that she had going on. In 1999, she published those poems in a book called Thoughts. When T-Boz showed her “Unpretty” poem to Dallas Austin, TLC’s regular producer, he loved it, and he adapted it into a song. In that same Billboard article, Austin says, “At the time, I was listening to a lot of folk and alternative artists like Ani DiFranco and Tori Amos. I was trying to figure out a way to bridge that into TLC’s music, because I knew that would make them different [compared to] everybody else. By having an acoustic-driven pop song, that would take them to a whole ‘nother place they haven’t been before.”
The idea of a TLC track that aims for Ani DiFranco/Tori Amos territory only seems strange if you’ve never heard “Unpretty.” With “Unpretty,” the group completely pulls it off. The song works so well in part because it’s so direct. There’s no flowery pretension to T-Boz’s lyrics. Instead, she spends the song working through conflicted feelings with an ease that’s almost conversational: “I tried different ways, but it’s all the same/ At the end of the day, I have myself to blame/ I’m just trippin’.” (That “I’m just trippin'” bit kills me. Here’s this woman bringing up all these raw-nerve emotions but still reminding herself not to take everything too seriously, the way real people do when they’re not fully willing to admit how down they are.)
T-Boz’s “Unpretty” chorus is all about the kind of validation that can only come from inner confidence, which can be so elusive for so many of us. TLC sing about hair extensions and nose jobs and MAC cosmetics, and they don’t degrade any of those options, but they also make the point that you’ve got to be able to “look inside you.” Some of the song seems to be T-Boz talking to her boyfriend: “Why do I look to all these things to keep you happy?/ Maybe get rid of you and then I’ll get back to me.” But “Unpretty” isn’t a relationship song. It’s almost entirely internal. Maybe T-Boz isn’t even addressing a boyfriend there; maybe it’s just the voice in her head. Maybe T-Boz is admitting that she’s the one who makes herself feel so damn unpretty.
Lisa “Left Eye” Lopez doesn’t appear on “Unpretty,” though she did rap a verse on an “Unpretty” remix that’s built from a sample of Dennis Edwards’ “Don’t Look Any Further,” a 1984 single that peaked at #72. The main version of “Unpretty” is T-Boz and Rozonda “Chilli” Thomas going back and forth about being stuck on their own perceived flaws. Throughout the song, T-Boz and Chilli acknowledge the idea that people think they’re attractive. T-Boz: “I was told I was beautiful, but what does that mean to you?” Chilli: “My outsides look cool, my insides look blue.” It doesn’t matter that other people think they’re pretty. They still feel that same inadequacy.
T-Boz’s delivery on “Unpretty” just kills me. The track turns her usual languid slide into something else. She still sounds smooth on “Unpretty,” but she lets some hoarse rawness into her voice, a slight tweak that changes the whole feeling of the song. At the end of the track, T-Boz lets out a laugh, and I’ve always wondered about that laugh. It’s not exuberant, exactly. I’d call it a sad cackle if the term “sad cackle” didn’t look like such a contradiction in terms. I hear that laugh as T-Boz’s way of reassuring us when the song’s coming to its close — her signal that the mere act of singing the song has made her feel a little better. I hope it did.
Dallas Austin’s music for “Unpretty” is twinkly and reassuring. “Unpretty” doesn’t really sound like an R&B song at all, except in the vocals. Instead, Austin goes full Lilith Fair, surrounding T-Boz and Chilli’s voices with a martial drumline and with strummy acoustic guitars. There’s some ragged power-chord stuff in there, too, and a quick solo as the song reaches its conclusion. (That guitar comes from Tomi Martin, a session musician who played on a lot of OutKast records and who toured with a lot of big stars, including TLC.) Austin also layers Debra Killings’ backing vocals, creating a sort of supportive choir that seems to be lending a sympathetic ear to the lead vocals. The whole thing just kills me. It’s so gorgeous, so graceful, so vulnerable, so real.
In their classic incarnation, TLC really only lasted for three albums. Those three albums came years apart, and they all landed at vastly different points of R&B’s evolution in the ’90s. All of those records fit their respective moments beautifully, and all of them seemed to adapt effortlessly to changing climates. The group’s actual history was chaotic and frustrating, but you couldn’t hear that chaos or frustration in their music. Instead, TLC just kept growing and developing. For me, “Unpretty” is the ultimate example of that. It’s TLC tapping into a sound that existed far outside their wheelhouse and absolutely nailing it. “Unpretty” isn’t a pop group reaching for a trendy style. It’s them using new muscles to say something that they didn’t feel ready to say before. I get a lump in my throat every time I hear it.
The “Unpretty” video, from director Paul Hunter, is a bit of a mess. It shows the members of TLC drenched in eye-bleeding color, amidst some of the ugliest CGI that the late ’90s had to offer. On the one hand, I like how the spaceship-R&B era came to affect songs that definitely don’t sound like anything that should be played in a spaceship. Left Eye had the idea for TLC to sign out the song’s lyrics in ASL, which is cool, and the members of TLC look luminous — a nice way to acknowledge that the people who feel unpretty probably aren’t that way in real life. On the other hand, the song deserves something less gaudy, and the various storylines all play out in the clumsiest, most obvious ways. But the video isn’t what defines “Unpretty.” The song does that just fine on its own.
“Unpretty” shouldn’t have been the end, but that’s what it was. TLC’s FanMail album went platinum six times over, mostly on the strength of “No Scrubs” and “Unpretty.” The group’s next single was the ballad “Dear Lie,” which was adapted from another one of T-Boz’s poems, this time by Babyface. It peaked at #51. “Silly Ho,” another FanMail track, was only ever released as a promotional single, but it still made it to #59 on airplay alone.
By the time that “Unpretty” reached #1, TLC were nearing the end of their FanMail tour, and they were falling apart. Left Eye had briefly quit the group before they recorded FanMail, and she was always halfway out the door. T-Boz and Chilli would complain in interviews about Left Eye being a flake, and Left Eye would shoot right back at them. Two months after “Unpretty” reached #1, Left Eye wrote a letter to Entertainment Weekly challenging her bandmates to make a triple album, with all of them doing their own solo work, to see who was really the best. She also called herself “the creative force behind TLC.”
Once the FanMail album cycle ended, Left Eye started making a solo album. It didn’t go well. Her single “The Block Party,” which is truly pretty bad, was a top-20 hit in the UK, but it missed the Hot 100 completely. Her album Supernova got a European release in 2001, but it never came out in the US. By that point, Left Eye was arguably bigger in the UK than in the US. She’d already rapped a guest-verse on the former Spice Girl Melanie C’s 2000 single “Never Be The Same Again,” which topped the UK charts and didn’t appear on the Hot 100.
Left Eye patched things up with the other two members of TLC, and the group started to record their FanMail follow up. In 2001, they sang “Waterfalls” together at MTV’s 20th-anniversary special. It would be their last performance together. In 2002, during a visit to Honduras, Left Eye crashed her rented car, and she died at the age of 30. It’s impossible to say what such a gifted, magnetic weirdo would’ve been able to accomplish later in her career.
TLC decided to finish the album that they’d started making, and that album, 3D, came out later in 2002. 3D went platinum, but it didn’t sell anywhere near as well as TLC’s previous records. Lead single “Girl Talk” peaked at #28. Two years later, T-Boz and Chilli starred in the reality competition show R U The Girl. UPN promoted the show as a search to find Left Eye’s replacement in TLC, but the group members said that they were only looking for someone to perform and record with TLC once, not to become a full-time replacement member. They knew that nobody could ever replace Left Eye. Tiffany “Krispy” Baker, the show’s winner, appeared on one TLC track, 2005’s “I Bet.” It didn’t chart.
T-Boz and Chilli’s personal lives remained tumultuous after Left Eye’s death. T-Boz married and then divorced West Coast rapper Mack 10, taking out a restraining order on him after their breakup. Chilli broke up with Dallas Austin and spent a while dating Usher; she inspired a bunch of songs that will eventually appear in this column. In 2013, T-Boz and Chilli appeared, as TLC, on J. Cole’s single “Crooked Smile,” which peaked at #27. (Cole’s highest-charting single, the 2021 21 Savage/Morray collab “My Life,” peaked at #2. It’s a 7.)
2013 was also when VH1 aired the made-for-cable biopic CrazySexyCool: The TLC Story. The movie was a ratings hit, and TLC gave a few performances with Lil Mama, the rapper who’d played Left Eye in the film, standing in for Left Eye herself. (Lil Mama’s two highest-charting singles, 2007’s “Lip Gloss” and the 2008 T-Pain/Chris Brown collab “Shawty Get Loose,” both peaked at #10. “Lip Gloss” is a 9, and “Shawty Get Loose” is a 6.)
T-Boz and Chilli have kept performing as TLC in the years since. They also used Kickstarter to raise the money to record their 2013 album 20. Just last month, TLC played Glastonbury. I hope they’re both doing great now, even if TLC doesn’t really seem like TLC without Left Eye. If I were them, I’m sure I’d be doing the exact same thing. In their day, TLC did a whole lot of incredible things, and the group’s surviving members deserve to coast on those incredible things for the rest of their lives.
BONUS BEATS: Here’s video of Taylor Swift playing a solo-acoustic “Unpretty” cover at a 2011 show:
(Taylor Swift will appear in this column a great many times.)
BONUS BONUS BEATS: Here’s Kelly Clarkson singing a remote cover of “Unpretty” on a 2020 quarantine-era episode of her talk show:
(Kelly Clarkson will eventually appear in this column.)
The Number Ones: Twenty Chart-Topping Hits That Reveal The History Of Pop Music is out 11/15 via Hachette Books. You can pre-order it here.