Showbiz always comes for the teeth. Early in Sean Paul’s career, at the start of the millennium—nearly two decades before Cardi B rapped about aspirational dental surgery on “Bodak Yellow”—the Jamaican musician embarked on a global debut with cornrows in his hair and braces on his teeth. The intended effect of the makeover? To align Paul with the big-budget hip-hop and R&B stars of American urban radio in the early aughts.

In order to cross over and become successful beyond the confines of dancehall, a genre then in the shadow of Bob Marley posters plastered on college dorm walls, Sean Paul would first have to go pop. Dutty Rock fits the template of how global pop breaks today: take an indigenous sound, affix it to a pop template, and attach a legible ambassador to the project (orthodontics may be required). This is the price of access to a monolithic industry. But now, after dancehall has once again gone mainstream, the stakes of crossing over are higher. Audiences are more open to genre, but they also have shifting and conflicting values and are more vocal about equity issues within pop culture, such as representation and cultural appropriation.

But before all of this, in the late ’90s, Paul was a bald-shaved, baby-faced loverboy proselytizing the hollowed-out cadence and bark of dancehall OGs like Super Cat and Shabba Ranks. Me and my friends drove around listening to flea market-sourced riddim mixtapes and hitting repeat on tracks like “Baby Girl,” “Infiltrate,” and “Deport Them.” The bass made our bodies vibrate and Paul’s boy-ish chat felt less intimidating than the grown-up raunchiness of other artists we loved, like Mr. Vegas and Elephant Man. Before he conquered the world, Paul’s club-ready dancehall was a kind of guide to our suburban adolescent mating rituals.

His first album, Stage One, barely hit the Billboard R&B/Hip-Hop 100 in 2000. A majority of the music on Stage One, including now-classic tunes like “Deport Dem,” and “Hot Gal Today,” had been floating around on riddim tracks for a couple of years before the release. But its lackluster commercial performance might also be indicative of incompatible listening cultures, or: conversational, informally distributed riddims versus the individualist, heavily categorized and marketed nature of modern LP making. “Riddims were an economic thing,” Sean Paul told me in 2016. “The tape could hold a certain amount of tracks, so there’s one producer and he has many artists on [the riddim]. That struck such a vibe in Jamaica because it was cool to hear different perspectives. You could have one guy singing about a girl with a fat ass, and another person singing something more conscious—and it’s on the same riddim.”

Thematically, dancehall is seeded in the thorny social morass left behind by colonialism. From its origins in the late 1970s to the present day, the music has often chronicled, “the gritty realities of Kingston’s ghettos...sharing crude truths about the conditions of Kingston’s poor, their connections to Jah (Rastafari for “God”), the medicinal and recreational benefits of smoking weed.” Paul was an uptown kid with an artist mom and an incarcerated father, who grew up playing competitive water polo. “A lot of my first songs were really conscious,” Paul said. “A couple of songs I wrote for my demo were talking about the ghetto story—I was drawing comparisons between uptown, where I’m from, and downtown.” But it was the gyalis tunes about chasing, watching, and dancing with women, that would become his niche.

In 2002, Sean Paul’s second album, Dutty Rock, hit big. By then he’d “gone international” after guesting on “Money Jane,” a posse cut by Toronto’s Baby Blue Soundcrew, which became an unexpected success on Canadian commercial radio. By the time Dutty Rock dropped, its first single “Gimme The Light” had already warmed up the clubs and streets via the Buzz riddim, a crackling, suspenseful loop that sounds like a tiny string section trapped in the digital chaos of a video game. It peaked at No. 7 on the Billboard Top 100—and then “Get Busy” leap-frogged it to reach No. 1 with a raucous music video in tow. Filmed in an unfinished basement in the suburbs of Toronto, the video by Director X prominently featured kinetic dance crews performing the latest dancehall moves and captured the innovative energy of a culture in diasporic translation.

The videos from Dutty Rock immortalized trends originating in Kingston dance halls, with help from Director X and perceptive choreography by Tanisha Scott. The visuals were also in conversation with what was happening on BET and MTV. In the video for “Like Glue,” Paul’s brother gets on the mic, calling out dance moves as a crew performs on stage: “row the boat,“ “signal the plane,” “parachute.” Just the year before, in 2001, everyone—from Diddy to a bunch of kid dancers—was doing the Harlem Shake in G. Dep’s videos for “Let’s Get It” and “Special Delivery,” and the decade would go on to birth the Dougie, Stanky Leg, Crank Dat, and more.

Dutty Rock also gave mainstream audiences a glimpse at the emotional complexity of dancehall. Scott’s choreography is precise, dramatic, and intimate, (her Kate Bush-meets-Patra work for Drake’s “Hotline Bling” captures this dynamic!). In the video for Dutty Rock’s third single, a cover of Alton Ellis’ twinkling 1967 track “I’m Still In Love With You” featuring Sasha, the waist-to-waist ballet reveals the promise of affection that keeps people on the floor until late. It’s tenderness between friends and (heterosexual) lovers: girlfriends, getting ready to go out and circling their hips to the beat in a bedroom mirror, and the charged delight of two strangers finding a rhythm within the competitive silo of the club.

Some dancehall fans consider the ’90s and early aughts a kind of golden era when production was precocious, raw, and experimental. Dutty Rock was a success because Paul’s tectonic hooks and uncanny pop melodies brought out new undertones to the gritty and ingenious riddims that are a staple of Jamaican production. The harpsichord intro to “Can You Do The Work,” on Jeremy Harding’s Liquid riddim conjures the odd pageantry of monarchical period dramas, but it’s Lenky’s clappy Diwali riddim, on which Sean Paul recorded “Get Busy,” that is totemic. It is peak creativity, a deceptively simple loop that conjures movement like a snake charmer’s horn. There’s a sample of the folksy syncopated handclaps that power the traditional Punjabi giddha dance, a hollow and steady bass drum to keep pace with a racing heart, gasping vox synth patches, and a sensual otherworldly whining noise, among others whimsical effects. It fit right in with the mass appeal, shiny suited, post-9/11 Orientalist hip-hop of the time, of which Timbaland and Missy Elliott were chief architects. Although Paul has noted that tracks like “Get Busy” and “Gimme The Light” were polished “by foreign mixers from America so that it could sound as big as whatever Justin Timberlake song was playing on the radio in the States.”

Lenky said that around 2001, "No one wanted [Diwali Riddim] because no one knew what it was. I was trying to give it to [vocalists] and they say it was too ‘noisy-sounding,’ so I put it back in my drawer." By 2002 it took off, and a collaboration with Paul was sorted. “Get Busy” went on to become their first U.S. No. 1 song, and that win paved the way for arguably the best song on the riddim: Wayne Wonder’s “No Letting Go.” That track was also a Billboard smash, as was Lumidee’s take, the charmingly off-key teen anthem “Never You Leave (Uh Oooh, Uh Oooh).” Lenky’s ingenious production spent multiple years on the globals charts, and Paul’s place as the world’s translator of Jamaican pop music was secured.

And then came “Baby Boy,” the Scott Storch-produced Beyoncé duet that was included in the international re-release of Dutty Rock. It’s probably Sean Paul’s most profitable single: 17 years after release, Beyoncé still performs it as part of her live show. For the singer’s Homecoming performances at Coachella 2018, she played “Baby Boy” as a medley, cut with interpolations of Tony Matterhorn’s frenetic “Dutty Wine,” the staccato dembow of the Fever Pitch riddim, and Dawn Penn’s blissfully lovelorn “You Don’t Love Me (No, No, No).” Years before Beyoncé became an arbiter of Black diasporic pop, she was looking to the Caribbean, and Paul was the gateway.

There has always been a bit of pushback to Paul from some dancehall fans because he’s a light-skinned, racially ambiguous artist from the relatively affluent “uptown” Kingston. Moving conversations about equity and appropriation forward requires consideration about the kinds of artists often received as innovators within genres, like dancehall, that long functioned independently of the commercial industry. A globalized music industry churns on the fracking of flourishing Black musical and aesthetic traditions, for consumption (and interpretation) by outsiders: from Snow to Apache Indian to Paul Simon to Justin Timberlake... to the entire K-Pop industry. Artists like Diplo, Bad Gyal, Ramriddlz, and Drake populate the current iteration of this debate as it pertains to dancehall.

Given that he was born and raised in Jamaica, Paul’s worldwide success might seem more comparably equitable. But the price of international stardom, or crossover success, remains legibility. Does crossover success empower anyone other than the artist in question? What could counter “appropriation” in a way that doesn’t rely on a neocolonial institution like the music industry? An AllMusic.com review from the time described Dutty Rock as “almost revolutionary.” If we were to revisit that statement today, it might be important to ask: revolutionary for who?