If you had to pick one ’90s popular music act that, success notwithstanding, should’ve been far luckier than they were, TLC would have to be on your shortlist. Few groups of the era had their uncanny blend of chart success and tragic turmoil: As their sophomore album, CrazySexyCool, shot singles “Creep” and “Waterfalls” to the top of the charts and sold nearly two-dozen million copies worldwide, Lisa “Left Eye” Lopes was fighting her alcoholism in rehab and struggling with the reputation the media dropped on her when she accidentally burned down the mansion belonging to abusive boyfriend Andre Rison. Tionne “T-Boz” Watkins, who’d dealt with sickle cell anemia since she was a child, would spend much of her time in and out of the hospital.

And in the summer of ’95, at what seemed like the absolute peak of their rapid ascent to success, the R&B/hip-hop superstars stunned the industry by filing for bankruptcy. As it turned out, their contract with management company Pebbitone Inc. and record company LaFace charged them for every single personal, recording, and touring expense they could while paying them all of 8% in royalties for album sales — less than 20 cents for each member of the group per album sold. If any band had been thoroughly victimized by Industry Rule #4,080, it was TLC.

That’s just part of why it took nearly five years to record a follow-up to one of the decade’s best-selling albums. Intra-band tensions and financial/creative disputes with producer Dallas Austin made the recording of FanMail a big question mark for a while, but when it finally came together in early ’99 — with the help of Jimmy Jam & Terry Lewis (“I’m Good At Being Bad”), Jermaine Dupri (“My Life”), Diane Warren (“Come On Down”), and Babyface (“Dear Lie”), along with a grip of Austin co-writes and productions — it seemed poised for success. All they had to do was pick the first single.

They’d have a comeback regardless. But releasing “No Scrubs” as the lead single from FanMail on February 2, 1999 — three weeks before the album dropped — made it a genuine phenomenon, and an ironic statement from a band whose financial difficulties were well-publicized. Before long, they’d inspire numerous answer songs, raise questions about gender and class that the song only hinted at, and give a previously obscure songwriter/producer a short but star-studded run at the top. Kevin “She’kspere” Briggs co-wrote “No Scrubs” with former Xscape members Kandi Burruss and Tameka Cottle (and a rap from Left Eye, at least on the single version). And no sooner had it gone to #1 than he found himself co-creating some of the biggest hits by Destiny’s Child (including the similarly financial-minded “Bills, Bills, Bills”) and Pink (“There You Go”), more modest-charting singles by Usher (“Pop Ya Collar”) and Whitney Houston (“One Of Those Days”), and album cuts for Mariah Carey (“X-Girlfriend”) and NSYNC (“It Makes Me Ill”).

The message of “No Scrubs” was simple: I can’t stand a broke-ass man. There might have been worse kinds of men in TLC’s lives over the previous few years, but a scrub — some dude “hangin’ out the passenger side of his best friend’s ride/ trying to holla at me” — was the most dot-com-boom-era style of loser, namely the kind without money. On the one hand, it might be a kind of hypocritical thing to hear from a group that actually went Chapter 11 so they could renegotiate a record contract that left them destitute. On the other hand, the underlying sentiment of it all — that they didn’t need a deadbeat, someone who wouldn’t stick around to pull their own weight, someone whose financial instability went hand-in-hand with an instability in maintaining a relationship — was what held the weight of the song.

Still, watch the Hype Williams video with the largess of 1999 in mind, and it feels like an entirely different planet. At a time when “you live at home with your momma” is a common situation for twenty-somethings and “you don’t have a car and you’re walking” is a financial reality for city-living young professionals who have to forego a Kia for student loan payments, the message of “No Scrubs,” especially in video form, almost feels like it’s on the wrong end of a class struggle that hadn’t yet invaded the popular imagination. All the whooshing CGI titles and gleaming space-age backdrops have this verge-of-Y2K futurism that feels like it’s transmitting from a future that wound up endlessly deferred because we all wound up too broke to reach it. It’s staggeringly charismatic in a way that still feels like the best kind of half-unreal pop art, where smooth-but-funky R&B is color-saturated against a stainless steel backdrop and those close harmonies find all the hidden rhythmic angles of that stripped-down synthesized Spanish guitar-driven beat. It’s just weird to experience a song from 20 years ago and realize it sounds even more aspirational than it did back then.

Not that it wasn’t clapped back at for that very reason (and some other, far less generous ones). When a song’s #1 on the pop charts and the Jop charts, people are gonna notice, and if it involves women talking shit about trash-dick men with sorry cashflow, a certain category of dude is likely get all itchy about it. Think about how another big pop-cultural institution of ’99 twisted some brains around the wrong way — thanks for that whole pill metaphor, The Matrix — and it’s easy to wonder how many fragile male egos the prominence of “No Scrubs” steered towards their own satellite locations of the He-Man Woman-Hater’s Club.

Sporty Thievz basically staked their career on it. The Yonkers rap group wasn’t a one-note joke or anything, but they became defined by semi-satirical answer songs that retorted against popular female-fronted R&B tracks of the time. And their first, most famous one came after their mentor Funkmaster Flex copped the rights to a track called “No Vultures” by NYC mixtape artists Mr. Wood$ and DJ Rhude, donating the track to Sporty Thievz and changing the titular bird from vulture to pigeon because the latter supposedly came across less harsh. “No Pigeons” dropped just three months after “No Scrubs,” piggybacking its success to a #12 Hot 100 peak (and, since they used a slightly faster, bassier variation of the original song’s beat, putting a few more bucks in She’kspere’s bank account). And their take was even more poor-shaming than TLC’s: it wasn’t enough that they had to deal with stuck-up women, it’s that they were “dirty braid Pigeons, Medicaid Pigeons, Section Eight Pigeons.”

DJ Quik’s response was even more cold-blooded — even if it was also a funk-rap club banger that’s pretty hard to not get down to. “Sexuality,” a track from his 2000 album Balance & Options, is dedicated to “all them bitches out there that think a n—a really supposed to pay they way through life, you know, like that ‘Scrub’ shit… it’s also dedicated to that chicken head bitch that wrote the lyrics.” The portrayal of a woman careening between sleeping around and looking for a steady relationship is, er, not kind: “Dude you could have this trashy bitch/ Put a down payment on her make me rich/ Thank you for helping me to change my mind/ You’re not my equal ho, fuck yo’ kind/ Can’t get mad if the bus don’t come/ I’ma just bail ’cause I trust no one/ ‘Cause everything that come up out your mouth is a lie/ You spend a lot of time with your stomach to the sky.”

Latter-day responses haven’t been all that great, either — they might not be as misogynist, but they seem kind of point-missing all the same. Just in this month alone we’ve been subjected to it as the through-line of a kinda tedious James Corden/Ken Jeong bit about local TV commercials and a mortifying Weezerfication that somehow won over Chilli. (That makes one of us.) But even if the song’s financial demands ring kind of strange at a time when youth and financial precarity are nearly synonymous, “No Scrubs” still deserves a better legacy than that (not to mention Ed Sheeran’s “Shape Of You” which was found to have jacked part of the melody). As an actual song — a beat, a performance, a group of vocal harmonies that conquered the ’90s on pure merit — it only stands stronger. Just play it smart, fellas: that anti-scrub policy is still well in effect.