It was April 1999, and Nelly was driving his close friend City Spud to a St. Louis police station. The pair were so inseparable and looked so much alike that they were often mistaken for brothers. They liked that, though Nelly and City would eventually dispell the notion. When Nelly dropped City at the precinct, it was the last time they would see each other before their lives split off into wildly different trajectories.

Days earlier, City, born Lavell Webb, was party to a botched robbery. He’d just quit his job at a North County McDonald’s and was relying on small-to medium-time weed deals to keep the lights on. On April 15, he was supposed to meet a potential customer for a $1,500 transaction. Customer gets off work, calls the pager, money and product change hands. Simple. The problem? Webb doesn’t have a car. The only person he found to drive him had proposed a new plan: instead of the arranged handoff, they’d rob the buyer, netting a grand for the driver and $500 for Webb, who could simply stay in the car.

Webb reluctantly agreed and waited in a parking lot near the mark’s home while the driver, masked and armed, headed out on foot. Minutes ticked by. Then: gunshots. Webb turned his head and saw his accomplice running back to the car; when he slumped into the driver’s seat, he was holding only $30. “Man, I had to pop him,” he said.

Police found the victim wounded but alive. He told the cops that his assailant knew about the $1,500 in his pocket, information that could have come from only one source: Lavell Webb.

Word trickled out that the cops were looking for him. Webb’s grandmother and her husband, who had been visited by detectives, urged him to have someone take him down to talk to the police. The husband told the Riverfront Times in 2001 that he feared what would happen if Webb laid low: “These trigger-happy cops—a young black man fleeing—were going to kill him.”

Barely more than a year after the robbery gone wrong, Webb would have four production credits and a show-stealing guest verse on Country Grammar, one of the best-selling rap albums of all time. But his royalties would only be topping off commissary accounts. Despite turning himself in, aiding with the investigation, and even helping to search for the gunman, Webb was arrested and charged. He eventually plead guilty to first-degree robbery and one count of armed criminal action, and was sentenced to ten years on the former, three years on latter, to be served concurrently. (Missouri’s mandatory minimum sentencing laws required that he serve 85 percent of his time before the possibility of parole.) Without his confession, the only evidence police had was circumstantial.

Just after City was locked up, Nelly would become a global superstar in commercial tugs-of-war with N’SYNC and Britney Spears. He and City’s work with the St. Lunatics—a tight-knit group of friends they met in high school and on youth sports teams—would define rap in St. Louis for years to come and net them millions upon millions of dollars. Kids across the country learned to wrap their tongues around “It’s all good—Range Rover, all wood” all while the man who rapped that sat in a jail cell because he didn’t actually have a car. Two friends diverged because the criminal justice system, and life itself, can be cruel and arbitrary. But Country Grammar was different: Country Grammar was a statement of purpose that gave order to the corner of the world Nelly and his friends inhabited, a syntactical maze of local culture that doubled as a flier for the greatest party you could ever imagine.

It almost never happened. Born in the fall of 1974 in Austin as the son of an Air Force man and a mother who worked mostly in fast-food restaurants, Nelly bounced from city to city. His parents divorced before he was ten years old; he was kicked out of a handful of schools, often for fighting other students. “There was a point in time when my mother couldn’t afford to keep me, and my father couldn’t afford to keep me, so I lived with friends, grandparents,” he told Rolling Stone in 2000. “When you a kid, that type of shit affects you. You don’t see that it’s not because they can’t afford you, you just feel that they don’t want you.”

He eventually settled with his mother in University City, a suburb on St. Louis’s West side. Nelly was an exceptional athlete, a shortstop who wore #1 and did backflips like Ozzie Smith, who was good enough to be invited to prospect camps for the Atlanta Braves, Pittsburgh Pirates, Milwaukee Brewers, and even the Cardinals. He also played wide receiver and led his high school team—the same high school that Tennessee Williams went to—in catches. But his time was divided between sports and another kind of extracurricular: “Nelly was going to either be a number-one rapper or a number-one drug dealer,” Murphy Lee, a friend and member of the St. Lunatics, told Rolling Stone. “One or the other.”

And so the legal perils, grave and petty, that plagued so many kids in University City were a constant threat. On “Greed, Hate, Envy,” one of the first songs on Country Grammar, Nelly says he “opened up shop at 13”— dimes, dubs, quarter-sacks, and o-zs. Later on the song, he dedicates a whole verse to an imagined traffic stop, where he taunts the officer, brandishes a squeaky-clean glove box, then laments as he drives off: “You could tell he was pissed ‘cause the black man in the black Range/Doing black things with his black change/Doing the right thing—driving his ass insane.” (”Greed, Hate, Envy” was produced by City Spud.) On the album’s emotional closer, “Luven Me,” Nelly credits his mom for echoing City’s grandparents. Quoting her: “Ain’t nothing I can do when them laws get they hands on you.”

By 1993, Nelly had teamed up with City Spud, Ali, Kyjuan, and Kyjuan’s little brother, Murphy Lee, to form the St. Lunatics. Save for Murphy, the ‘Tics were finishing up or already graduated from high school. (When Country Grammar came out in 2000, Nelly was 25, but shaved four years off his age for the press, a discrepancy that was quietly corrected later in his career.) A sixth member, the perpetually masked Slo’ Down, was subsequently added to and then dropped from the group, though he was functionally a hype man and had little creative input. The group had some early success in 1996, scoring a serious local hit “Gimme What U Got” that sampled Le Pamplemousse and Tom Tom Club and buried vocals from “La Di Da Di” deep in the mix. In the video, the ‘Tics stood in a line and danced; they quoted Rakim; they skipped through comically calm barbershops. It was fun, it was summery.

On record, Ali was the group’s de facto leader: gruffer and more guttural than the other members, clearer and more commanding. That’s him in the Brett Favre jersey, heading straight to the bar for Henny and Coke. But the last verse belongs to Nelly. There’s a rambunctious verve to his delivery—maybe a little too freewheeling for the track—and a magnetism that cuts through even the goofiest camera work.

Despite the considerable buzz that the single generated around St. Louis, labels wouldn’t bite. “We were shopping the Lunatics at the time,” Nelly told Complex in 2015. “And nobody was tripping off our sound or giving us a shot.” Eventually, the group settled on a strategy: pitch one artist as a solo act to get a foot in the door and come back for the rest as soon as possible.

A CD made its way to one of Mase’s managers, and Nelly flew to New Jersey to flesh out a demo. He landed on four songs: “E.I.,” “Ride wit Me,” “Batter Up,” and “Hot Shit,” which would later be retitled “Country Grammar.” When he finally secured a contract, it was with a young A&R at Universal named Kevin Law, who had never before signed a new artist. (The Lunatics also landed a group deal, but it was contingent on Nelly’s record hitting certain sales thresholds.)

Universal agreed that Nelly was a better bet on his own, but his record was still far from a priority. The ten songs not included on the demo tape were finished in New York in “three weeks in a little shithole studio and a little-bitty-ass budget,” as Nelly characterized the situation to Rolling Stone. The album was slated for a summer 2000 release.

At first, the label was reticent to go with “Country Grammar” as the lead single, despite its popularity in St. Louis. They set aside $150,000 for the video—a sizable budget by today’s standards, but practically a vote of no-confidence at the turn of the century. Law came up with the now-famous radio edit (the percussive boom-boom in place of “street-sweeper” in the chorus) and sent it out to DJs before Nelly had even heard it.

With the benefit of hindsight, the song and its video seem like Nelly distilled. It opens with him tapping on the camera to get your attention: there’s Nelly, shirtless under a blue sky and the Gateway Arch, a red Cardinals cap laid backwards over a white durag, chain dangling. More accurately, it was a codification of the most interesting elements in the early St. Lunatics work, a fledgling style isolated and carried to its radical end. The bounce and swing that had served as undercurrents on “Gimme What U Got” became “Country Grammar”’s driving force; the chaos of Nelly’s early raps was quieted, the energy channeled into a sing-song delivery that made drive-by shootings sound whimsical.

It’s difficult to think of a music video that puts on more aggressively for its city. The block party scenes were shot a block away from Nelly’s Labadie Avenue home; there are Cardinals jerseys, Blues practice sweaters, Orlando Pace Rams jerseys worn backwards in the thick of the Greatest Show On Turf era. “Country Grammar” was so irresistible that Michael Jackson called Nelly personally to express his love for the song, then gave the Lunatics tickets to his show, where they were seated beside a pre-“Apprentice” Donald Trump. Trump, like Michael, was a fan, and particularly appreciated the shout-out Nelly gave him in the song’s third verse. (Both Jackson and Trump caught barbs elsewhere on Country Grammar: on “Tho Dem Wrappas,” Nelly says he’ll have “SoundScan like Thriller without changing my face,” and on “E.I.,” he raps about booking “a room at Trump Towers just to hit for three hours.”)

Country Grammar often feels like a Trojan Horse for the St. Lunatics. “Steal the Show,” “Batter Up,” “Wrap Sumden,” and “Thicky Thick Girl” feature members in various combinations. The diction—as Cedric The Entertainer, who invited the ‘Tics to perform at his shows when they were starting out, puts it on the album’s intro, “Puttin’ them two capital Rs in everything”—gives it a thoroughly regional air. The syntax has the same effect: girls are thicky thick girls, everybody’s “Mo.” At points, the album finds crevices in St. Louis’s underbelly or in Nelly’s psyche, but its natural habitat is a weekend afternoon, when friends lazily assemble, roll up, make liquor store runs, and try to conjure the perfect plan for later. It’s right there in “E.I.”’s operative question: “What’s poppin’ tonight?”

Nelly brings the parties to life with a charming specificity. In the verse from “E.I.” that ends in a Trump Towers suite, Nelly makes a shower and outfit change sound like a carefully executed heist. And the house party on “Steal the Show” spills out where it doesn’t belong: “Neighbors on the lawn, like, ‘Nelly, why right here?’” (”Here,” of course, is “hurr.”) The production, handled principally by Jay E and City Spud, often sounds like it could have been lifted from Hot Boys sessions, but benefits from bits of country flair and from the Midwest swing that Nelly brings to the mix.

St. Louis is rendered mostly in glimpses and fragments: the corner of Natural Bridge Avenue and Kingshighway Boulevard is pinpointed without elaboration, and the Plaza Frontenac, an upscale mall, is made to sound like the Taj Mahal. We hear about basketball hoops fashioned from milk crates and illicit monopolies in North County. There’s little hand-holding for outsiders, but plenty of hints at the gloss or horror that’s lurking six blocks in any direction.

The singles aside, Country Grammar’s two most thoughtfully written songs are also its best. “Utha Side” is like a reimagination of Masta Ace and Marley Marl’s “The Other Side of Town” for the dot-com boom, with crack swapped out for speed of all varieties. The song ends with a verse that manages to sound poised, even cool, while urging kids to stay in school—which makes Nelly’s eventual beef with a pious KRS-One all the more amusing. And “Luven Me” is endlessly touching: Nelly remembers his mother scraping together money to buy him name-brand clothing, only for him to turn around and sell dope on her front lawn and wreck two of her cars.

Cars are Country Grammar’s prevailing motif. Navigator, black sedan DeVille, red Expedition, a hooptie with insurance, the Mercedes, Cutlasses on the riverfront, the Range Rover the cops pull over. So maybe it’s unsurprising that the album’s highest-charting single is about driving. “Ride Wit Me” was issued to radio in April 2001—ten months after Country Grammar came out, and exactly two years after City Spud was arrested and charged. It’s an absurdly catchy song, full of slick guitar and feigned frustration and cash-couched call-and-response. It’s propulsive. Nelly talks with sheer, unmitigated joy about washing his hands of cocaine or about putting cars in his own name now, without his mom’s co-signature; he raps, “Damn, shit done changed now/Running credit checks with no shame now.” City’s verse is unveiled after a huge, climactic crescendo, as if he were an A-list guest, not a kid from the Midwest who got caught up because he caught a ride with the wrong person.

By the time Nelly’s second album came out, in 2002, he was wearing a band-aid on his cheek as a tribute to City; the St. Lunatics album, which Universal did release after all, was named Free City. City was finally freed in 2008. There was certainly plenty of money to go around—Country Grammar would eventually be certified Diamond—but any realistic hope of breaking City as a mainstream star had passed. Nelly’s album from 2008, Brass Knuckles, debuted at No. 3, but was buoyed by bankable guest stars like Usher, Rick Ross, T.I., Nate Dogg, LL Cool J, and Snoop Dogg. (That list is from the first four songs.) What’s more, the instantly identifiable St. Louis sound that the Lunatics forged had been largely abandoned in favor of neo-G-Funk and aping T-Pain.

So the moment was gone, and with it the industry’s brief fascination with St. Louis (see: Chingy, J-Kwon). A singular, irrepressibly fun record that serves, at least in part, to honor friends and makeshift family became a sensation while one of those family members was locked away. And when they were reunited, Nelly no longer had the muscle or magic to turn every camera in the country to him, to St. Louis. His creative peak, though, was captured at exactly the right time. No matter how the sands shift around him, Nelly’s still there on the album cover, staring down, head cocked to the side, the Arch looping back behind him.