With all due respect to Death Row, no rap record label has ever consolidated and celebrated its power the way Cash Money Records did in the final year of the 20th century. All four albums the young crew released that year—B.G.’s Chopper City In The Ghetto, the Hot Boys’ Guerrilla Warfare, Lil Wayne’s Tha Block Is Hot, and Juvenile’s Tha G-Code—would be platinum by January 2000, propelled by outrageous swagger and Mannie Fresh’s electro-swamp beats. Cash Money’s members did everything at a more extreme rate than their competitors for radio and MTV airtime would ever dare. Their pimping was bigger than JAY-Z’s. They were more mambo than Lou Bega, higher than Tal Bachman, and hornier than Sisqó. They stole Len’s sunshine. They forced Master P into the Continental Basketball Association. And in a twist more bonkers than a Mannie Fresh ad-lib, they added a word to the dictionary by the time it was all done. It’s no wonder the Big Tymers were buying platinum football fields in the Y2K.

Money—as a theoretical concept and a promise as much as hard currency—was the gasoline combusting in CMR’s engine as they did doughnuts on the Top 40. The label had been founded in New Orleans in the early 1990s by brothers Brian “Baby” (also “Birdman”) Williams and Ronald “Slim” Williams, who went from releasing bounce records to being players in the region’s hip-hop scene. In March 1998, Baby and Slim brokered an historic deal with Universal Records that netted Cash Money an estimated $30 million, 80% of royalties, and full ownership of masters and publishing, suddenly granting a handful of rappers, one in-house producer, and two bosses hailing from the notoriously rough Magnolia Projects an extraordinary amount of money, power, and freedom for self-determination. Cash Money immediately became one of the most valuable boutique labels on earth, worth more than JAY-Z’s nascent Roc-A-Fella.

Rapping about wealth was nothing new when the video for “Bling Bling” dropped a year later, in the spring of 1999; B.G. was fighting for Billboard space with Warren G’s “I Want It All,” to name but one example. But the Cash Money clique was practically rococo in its boasting. Juvenile’s 400 Degreez had already been conceived when the Universal deal was signed, and its two monster singles concerned life in the projects and the magnetic power of an unnamed woman’s ass, with videos to match. “Bling Bling,” with its outdoor feast, bushels of cash, private island, mysterious briefcase, legion of cars (including, somewhat incongruously, a New Beetle), and helicopter, seemed to come out of nowhere, especially for the huge, mostly white audience encountering them for the first time via MTV. Who were these dudes? How did they get all of this money? Why were they wearing pinkie rings? It was hard to tell how serious they were being.

What was clear was the boundless charisma shared by everyone on the track. Fresh, whose beat punches and twirls like a bounce track duded up for the Met Ball, claims to have bought a private plane, which he then sold in a joint venture to Juvenile and Lil Wayne, who in turn kit the jet out with 30-inch rims. Juvenile, leaning way over the front of a motorcycle, introduces himself as “a 1999 driver,” a lyric that had to have felt dated within a week, and which gets better with every passing year because of it.

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But it’s Lil Wayne who steals the show. On the day the group recorded “Bling Bling”’s radio edit, fellow Hot Boy Turk, who was struggling with a drug addiction, was high and ashamed to show his face at the studio. Always at the ready, Weezy punched in a verse that hints at the monster rapper he’d become. He shifts up his flow, running it over every gleaming facet of the beat, pulling back on the throttle to bump through a stuttering “no, nah, no, nah, no-uh, no he didn’t.” In the video, he pulls the front of his shirt back behind his head, shows off a flip phone, and basically looks like a star.

“Bling Bling” was a Hope Diamond of a track, impossible to ignore, its title phrase delivered with so much charm—and the video stuffed with so much giddy money-tossing—that it was inevitable it would become so ubiquitous in this era. The video played so frequently, Turk claims that his absence effectively derailed his solo career before it ever started, and he’s probably right, even though his debut, 2001’s Young & Thuggin’, sold over half a million copies.

The group dynamic was integral to the sound Cash Money was developing. Creatively, the label functioned like a flossed-out version of the Brill Building, with each of the rappers working simultaneously on whoever’s record was up next in the release cycle. They rarely recorded with outside artists, their endless ciphers instead rolling in a closed system that generated incredible amounts of heat. It also meant that their slang—“woadie,” “bezeled-up,” “the Nolia”—arrived on the national stage seeming like a fully formed language.

Some of their intrigue has to do with the insular nature of pre-Katrina New Orleans, too; not many rappers were casually referencing second lines on hit singles. Like any New Orleanian anxious about their cosmopolitan taste, Fresh likes to say that his production style is a “gumbo,” with ingredients pulled from around the country: a little West Coast swing, some East Coast class, whatever. As Simon Reynolds reported in The Village Voice, Fresh spent time in Chicago working with producer Steve “Silk” Hurley, and ripples of various electronic scenes pulse through his production, from boogie to acid house.

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But as anyone who’s eaten their fair share of gumbo knows, whatever you toss in the pot usually just ends up tasting like gumbo, and Fresh’s early style is as deeply New Orleans as red beans on a Monday and the Special Man financing your tufted couch. The Baroque arrangements and harpsichord tones he favored in his keyboards amplifies the rappers’ performative fanciness, like it’s mocking the uptight bling of the Rex Mardi Gras ball, while the drum programming is lacy and intricate, a cluttered grid of sound with just enough gaps for you to jump between, like a drum line playing cadences as it waits for the parade to start moving again.

Fresh’s production forced the rappers to be nimble, and it favored the kinds of call-and-response vocals that mark both bounce and the chants of the Mardi Gras Indians who would frequently meet at A.L. Davis Park across Washington Avenue from the Magnolia. Juvenile’s sing-song delivery and B.G.’s slurred chorus in Guerrilla Warfare’s “Boys At War” may as well be lifted from Wild Tchoupitoulas; in a nice bit of serendipity, the latter’s accent makes the title phrase sound like “them boys that walk,” which may as well be a reference to the spy boys who lead the way when the Indians come marching.

Streaking across 1999’s skies like water from a bottle being shaken over a crowd is the song that would define this era of Cash Money Records and New Orleans hip-hop generally: “Back That Azz Up.” The sudden shudder that runs through a club when Juvenile’s voice declares “Cash Money taking over for the 9-9 and the 2000” in the song’s intro, and the way a room tremors and jiggles and just fucking moves when Fresh’s drums start to kick, is the greatest evidence that we are, in fact, corporeal beings with actual bodies and not merely thought experiments in some greater mind. In Juvenile’s hands, it is purely physical music that celebrates the purely physical. (The less said about Fresh’s verse, the better, but suffice it to say that when André 3000 declared “The South got something to say” at the 1995 Source Awards, this isn’t what he was talking about.)

“Back That Azz Up” was released as a single on February 24, 1999, and spent 46 weeks on the Hot R&B/Hip-Hop Songs chart. Perhaps owing to the stifling humidity of New Orleans summers, it didn’t peak in popularity until September, when the action of backing that ass up was less likely to lead to dehydration. It is a perfect representation of everything Cash Money did well at the turn of the millennium: Juvenile resuscitating his skills as a bounce rapper to lead the crowd, Fresh layering mournful strings (which he says he included to hook “white America”) and banging the beat on the one like James Brown, Wayne tagging the song with his first great verse of sublime wobbledy-wobbledy nonsense.

The hits would keep coming, with Fresh and Baby’s Big Tymers scoring the next year. Mainstream rap would become more and more commercialized. Juvenile and B.G. eventually split from the label, but Wayne stuck around and built an empire, albeit one on someone else’s property and subject to that overlord’s whims. Young Money/Cash Money became the most powerful rap label of this millennium, but with global fame came a kind of flattened, globalized sound, Drake appropriating the “Triggaman” beat notwithstanding. If there’s a Cash Money aesthetic now, it doesn’t bear the imprint of the dudes that brung you “Put Up Your Solja Rags.”

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Which is inevitable. Things change, even in places like New Orleans that seem constitutionally opposed to it; there’s a James Beard Award–winning bar a short walk from what was once the Magnolia Projects. Juve’s now an elder statesman at the age of 44, “Ha” the kind of universally recognized masterpiece into which a rapper as highbrow as Kendrick Lamar can swerve with confidence. Fresh is so integrated into the New Orleans community he gets to DJ at Saints playoff games. Wayne is still a sensation capable of occasional greatness. But the temptation to revel in who they were in 1999 is nearly as difficult to resist as a Mannie Fresh beat. For all of its success in the ensuing 20 years, Cash Money Records never had another moment like this, when its artistic and financial fortunes were so deeply intertwined. That sense of impermanence was built into the music. Like the flash of light off a bezeled-out earring, it was gone in an instant, but you can still see it bling from here.