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Daddy Yankee Forever: A Reggaeton Legend Goes Out on Top

By Julyssa Lopez

Julyssa Lopez

T he August sun knows no bounds one sweltering afternoon in Las Vegas as it beats down over the slick, steaming asphalt roads of the Strip. At 6 p.m., it’s still a merciless 102 degrees outside, and there’s little hope that nightfall will cool down the neon-lit city. Yet outside of T-Mobile Arena, fans of reggaeton legend Daddy Yankee have started to line up to see him three hours before he’s due onstage. They wait patiently, braving airless temperatures and blistering dryness, their enthusiasm stronger than the heat.

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On the other side is Daddy Yankee, whose real name is Raymond Ayala — the sole force driving this moment, and the person so often credited with taking reggaeton global. Given that he’s a larger-than-life figure, admired across the music industry for his razor-sharp business acumen and some of the world’s biggest Spanish-language hits, it’s easy to imagine a pre-show ritual with a giant posse and glimmering bottles of Cristal. But there he is, standing completely alone in Zen-like silence, wearing sweatpants and a gray tour hoodie with the name of his most recent album: Legendaddy . “Raymond,” he introduces himself, pulling out a hand from his sweatshirt to shake mine.

People have dedicated a universe of tweets and memes to how young Ayala looks at 45, and in person, he’s even more boyish, with gigantic brown eyes that soak up every question thrown at him. Friends close to him say that he’s disciplined and self-possessed, though right now, he admits there’s a flood of emotions welling up in him. “This is a roller coaster,” he says, sitting down on a nearby black couch. “So many feelings come up.” He’s about to play a show that captures decades of hits, that hopefully nails all the favorites people came for. “I want every single generation out there to feel like this is dedicated to them,” he says.

His career can be measured by all the fans waiting for him, and the scatterplot of ages and demographics they represent. You could also trace it through the impact he’s had on his peers and on younger artists across Latin music, who talk about the path he’s charted with a sense of awe. “Time has never been the enemy for him — he’s kept adapting to what’s happening as every generation goes by,” the rapper Anuel AA says. “Daddy Yankee’s career represents the past, present, and future of reggaeton.” The singer Natti Natasha calls him a close friend and mentor: “I’d describe him as a family person, humble, down-to-earth,” she says. “I mean, he’s a living legend.” “Yankee is Yankee,” Rauw Alejandro adds. “There’s never going to be anyone else like him.”

Ayala himself has been thinking about what he’s achieved since picking up a mic as a teenager in Puerto Rico. He was among the pioneers who shaped the genre, and he has remained a perennial star until the end. “Everyone eventually does a comeback tour, but not Daddy Yankee,” he says, slipping into third person as he warms to his theme. “Since I started in reggaeton, I’ve been relevant. It’s like if Benny Moré or Celia Cruz were making salsa at this very moment and people go, ‘Papi, these people have the Number One album right now.’ Or if Chuck Berry were here and people ask, ‘Who’s the Number One artist making rock?’ and he’s the one still making all the hits.” Ayala is known for his modest demeanor, but he’s not willing to downplay this point: “There’s no artist who’s done this,” he says calmly. “It’s Daddy Yankee.”

AYALA STARTS LAUGHING when I ask him later about whatever alchemy leads to his onstage transformation. “I’m still trying to find an explanation for that,” he says gently. “I’m a contemplative person, I don’t talk a lot, I’m always calm. But when I have to go onstage or hit the studio, that side of me comes out. It’s like a lion — I think everyone has a lion hiding inside them.” He says he’s been that way since he was a kid, when he loved baseball and boxing. “When it was time to execute something, that chip would get activated.”

Ayala grew up in public housing in Villa Kennedy, a barrio in San Juan. He was focused on baseball for most of his adolescence — he played third base, and came close to signing with the Seattle Mariners — but he was also surrounded by music. His dad was a percussionist for salsa bands on the island, and his mom came from a family of musicians. Ayala sang as a kid, and learned he had a knack for improvisation during Christmas celebrations in Puerto Rico. “Whenever my family would go to a family member or friend’s house for parrandas , they’d bring me out and I’d start making up rhymes,” he says, referring to a tradition of going door-to-door to sing for loved ones during the holidays. As he got older, he’d write lyrics in his notebook and freestyle with friends.

Ayala stayed committed to sports until multiple tragedies changed his course. When he was about six years old, he watched as his coach Juan Cintron was gunned down on a baseball field, just behind home plate. Ten years later, when he was 16, Ayala had been recording with DJ Playero in Villa Kennedy, and he stepped out briefly to take a break. All of a sudden, a gunfight broke out, and Ayala was hit with a stray bullet. It’s lodged in his hip to this day. Though the incident effectively ended his baseball career, it ultimately pushed him to dedicate his life to music. “I thank God for that bullet,” he has said before.

Ayala released two albums before starting his own label, El Cartel Records, in 1997, when he was just 21. By then, he had a wife and kids — he married his high school sweetheart, Mireddys Gonzalez, at 17, and they’ve been together ever since. He was blowing up across the island, and artists and producers alike were seeking him out to collaborate. One person who reached out was Francisco Saldaña, a younger musician who was quickly becoming known as Luny, from the seminal production duo Luny Tunes . When he first met Ayala, Saldaña had just been involved in an island-wide reggaeton debacle: Several of the producers’ biggest songs, for pivotal figures like Tego Calderón and Don Omar, had been stolen from the studio where they worked and leaked to the public. Saldaña’s first offer to work together was rebuffed: “He was like, ‘You guys are pirating music!’” 

Luckily, they kept running into each other, and Saldaña felt they were fated to collaborate. They eventually agreed to make several tracks together, among them the rattling, no-holds-barred hit “Cójela Que Va Sin Jockey,” from Luny Tunes’ iconic 2003 compilation album Mas Flow . The song took off in clubs across New York and created a blueprint for the genre’s rapid expansion. “That’s where that style came from — after that, everyone tried to make tracks like ‘Cójela Que Va Sin Jockey,’” Saldaña recalls. “It was a song that opened doors for reggaeton.”

Ayala, meanwhile, was looking for lyrical inspiration everywhere, and a wave of it came one day in the most quotidian way: He was at home in his Villa Kennedy apartment when he heard someone on the street shouting, “Como le gusta la gasolina!” That phrase, he says, was a common one that described girls who were always looking for a ride to the next party. He worked out the rest of the song, tapping the Puerto Rican artist Eddie Dee as a co-writer. The sounds and the lyrics aligned in a rare moment of sonic perfection, and they had a megahit on their hands.

That snippet of Puerto Rican colloquialism — a tiny snapshot of everyday life on the streets of San Juan — traveled everywhere. “Gasolina” charted in Italy, Greece, and Denmark, just to name a few places, and helped make way for other reggaeton artists worldwide. It became the cornerstone of Barrio Fino , an album that’s still held up as a commercial breakthrough not just for Ayala, but for the genre in general. Saldaña notes that Ayala already had major hits and that those, along with albums such as Tego Calderón’s legendary El Abayarde and Don Omar’s brilliant debut The Last Don , built the foundation for the music in the years immediately preceding Barrio Fino ‘s 2004 release. “Yankee was promoting [ Barrio Fino ], the genre was exploding, and things were working — Tego, Hector Y Tito, Don Omar, Wisin & Yandel,” Saldaña says, naming other pioneers of the era. “All of it was working, and this one was going to work, too.”

Ayala felt it, too. “I think you can wish and plan [making an album like that], but to have it be a success — there’s always uncertainty in music,” he says. “With Barrio Fino , I knew I had something special, because I understood the culture it was coming from.” 

“They didn’t get it,” Saldaña adds. “They didn’t get what was happening. They supported it sometimes with the big acts, but not the whole genre.” 

But Ayala was an ambassador who the industry began to rally around. Triviño points out that he had both lyrical dexterity and a story people rooted for. He also had an image that was marketable by the Latin entertainment industry’s narrow standards, which often prioritize light-skinned celebrities. He was shrewd about his business moves, and he had a reputation for working nonstop. “I cannot keep up with him,” Saldaña says. “If he needs to stay up for three days without sleeping to finish a song, he does it. If he needs to go shoot a video after that, he does it. If he needs to jump on a plane to do a show after that, he does it. We’ll finish a song and I’ll be like, ‘No, I need to go sleep.’”

There were, of course, lulls in Ayala’s music and the reggaeton ecosystem at large in the years to come. Saldaña remembers how after one such dip, the 2012 viral hit “Limbo” helped revitalize Ayala’s sound and remind people of the strength of the genre. Even so, people had doubts. “I’d do interviews and people would say, ‘What’s happened to reggaeton?’” Ayala recalls.

We’re growing every day. If tomorrow a new genre comes along and it’s Latino, it’s going to be successful, because our cultural expressions and our art are going to keep rising.

But he always believed in the music, and saw firsthand how universal it remained, despite what the media said. “I’d be like, ‘With all due respect, but you guys don’t know. You guys don’t go out, you’re not going to the clubs,'” Ayala says. “They’d freeze up. I’d say, ‘What people listen to on the streets and out everywhere is reggaeton.’” 

HE PROVED HE was right a few years later. For an artist to have one “Gasolina” in his or her career is enough to make history. But in 2016, more than a decade after the song’s success, the Puerto Rican singer Luis Fonsi reached out to Ayala about a track he had been writing with songwriter Erika Ender. The melody was driven by a Puerto Rican cuatro, and he was calling it “Despacito.” Ayala met him at a studio in Miami and added a verse, while also suggesting a few changes, proposing they repeat “pasito a pasito” after the bridge. The song became another behemoth that changed Latin music for a second time.

Take what happened after Justin Bieber saw how huge “Despacito” was and joined the remix in 2017. Ayala has said that he was then asked to take a smaller percentage of the royalties as a songwriter, though he’s quick to explain it had nothing to do with his collaborators. “That happened, but it was about the labels,” he says. “I have nothing but marvelous things to say about Luis Fonsi and Justin Bieber.… But you take the artists out and you’re talking to labels, it’s a different game.” The business savvy Ayala is known for came into play: He stood firm, and he says one reason he was able to negotiate was because he remained independent through El Cartel Records. “When you’re independent, you’re free,” he says.

Following his success with “Despacito,” Ayala seemed to land hit after hit. There was 2018’s “Dura,” which currently has 1.8 billion views on YouTube. In 2019 came “Con Calma,” an unexpected smash that has 2.5 billion views right now. The song was a reimagining of the Canadian reggae artist Snow’s 1993 hit “Informer,” showing off Ayala’s keen ear and creative thinking: He took what had become something of a Nineties novelty song and brought it charging back to life. Other artists were constantly reaching out to him to collaborate, and he had unbeatable momentum.

Then the pandemic hit. As the world slowed down, so did Ayala. “I think the pandemic was like someone forcing the brakes on the world,” he says. He had been going for almost 30 years straight by then, and he had become intimately familiar with the grind of the industry. Though he’d always spent a lot of time in Puerto Rico, where he still lives, he wanted to spend even more time with his family, which includes his kids, now in their twenties, and Gonzalez, who is CEO of El Cartel Records. He felt that he was in a place where he could walk away and be proud of the work he’d done. “I was like, ‘It’s my turn to live instead of working, working, and working,” he says. “When I got into that reflective state, I said, ‘I need to live, too. I need an opportunity to actually enjoy everything I’ve achieved. I’m healthy, I’m good, I’m young.’” 

There were industry whispers about Daddy Yankee announcing his retirement, but Ayala’s frequent collaborator Juan Salinas, known as part of the production duo Play-N-Skillz, didn’t totally believe it until he got a personal call from the man himself. “I was devastated, to be honest with you,” he says. “But after talking to him and hearing his perspective, how he wanted to go out on a very respected and high note and put out a last body of work that was going to mean something after so many years of touring and media, it made sense.” Ayala told Salinas that he wanted his help putting together the last album, and they went to work.

Ayala worked with several producers in Puerto Rico, including Nekxum and Tainy, the superproducer who got his start in the 2000s as Luny Tunes’ 15-year-old protégé. Once Ayala met up with Salinas in Miami, they went to work every day at 3 p.m. “We didn’t go out, we didn’t fuck around,” Salinas says. “I like to drink and party while I make music … but there’s a limit [with Daddy Yankee] because he likes to be on point.” In between songs, they blew off steam by playing basketball or video games — all of which brought out Ayala’s intensely competitive side. “We lost hours because if he lost a game of horse or he lost a shooting game, he’d want to play again,” Salinas says. 

But Ayala’s real domain is the studio. “Yankee is more than just a rapper and a singer,” Salinas says. “The guy knows music. He sits down, he hits the keyboard sometimes with us. He’s like, ‘These are the chords, change the drums.’ His musical genius is way beyond just a rapper rapping 16 bars, or a singer belting a song.” “Play” and his brother Oscar “Skillz” Salinas ended up co-producing six tracks on the album, which went platinum in the U.S.

Salinas is still reeling over the role he got to play in Ayala’s career, and he loves how Legendaddy turned out. “It’s going to be really tough for anyone to say they’re going to have a retirement album after Legendaddy , because he planned it right,” he says. “He had the tour, he had the merch, he had the perfect name. The guy’s a chess player.” Salinas had a few words for Ayala afterward: “I said, ‘This is Floyd Mayweather shit, man. Floyd Mayweather retired, undefeated, 50-0 and never lost — a champion. That’s you, bro.’”

SINCE HIS VEGAS show, Ayala has continued crisscrossing the country on his tour bus. Before a show in Boston, his doctor advised him to preserve his voice as much possible, so he spends almost every day in complete silence. Instead of talking, he catches up on reading and watching shows on Netflix — he binges Ozark and Stranger Things, which he saw people talking about online. He avoids listening to music to protect his hearing. At night, he cooks elaborate meals on a tiny single-plate grill. He’s especially proud of his pork chuletas, which make it onto his TikTok.

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Outside his window, the terrain keeps changing. His bus rolls through Colorado and Oregon and Utah. He plays a string of shows in California, seeing parts of the state that are completely new to him. One thing, he says later, strikes him repeatedly: Back when “Gasolina” was exploding, he remembers seeing data that said Latinos were the fastest-growing segment of the U.S. population and that by 2050 the demographic would no longer be a minority group. He’s always understood the power of the Latino community, but he’s witnessing it daily as he travels: “We’re growing every day,” he says. “If tomorrow a new genre comes along and it’s Latino, it’s going to be successful, because our cultural expressions and our art are going to keep rising.”

He’s played more than 30 shows so far, always taking the stage before screaming crowds. Their excitement is obvious through their cheers and chants, but it’s hard not to wonder what goes through Ayala’s head when he’s up there performing. His voice gets quiet, and it’s not just because he’s worried about overexerting his vocal cords. “It’s hit me really hard,” he says. “A lot. I’ve been about to collapse from emotion onstage, but I can’t — the show has to go on. I think about the applause, all the people sitting there, in the beginning, the things I went through, the sacrifices. It’s so many memories.”

Fans — perhaps harboring a glimmer of hope that he’ll keep making music — have questioned if his retirement is real. Ayala is adamant that he’s done. “I don’t have any plans to go back,” he says.

The future is a giant, blank abyss that he’s diving into with the same resolve that’s powered his entire career. “I think that’s the coolest part. There’s a mystery there that I need to discover, and it’s what makes me the most excited,” he says. “I don’t know what’s going to happen.”

Produced by  Joe Rodriguez . Photography direction by  Emma Reeves & Joe Rodriguez . Fashion direction by  Alex Badia . Styling by  Marcus j. Correa . Set design by  Audrey Taylor For This Represents . Set design assistance by  Brendan Haegarty . Location WKND studios . Photography assistance by  SAUL BARRERA , EVERETT FITZPATRICK , and  DAVID BUNGE . Production assistance by  James Thornton III . Styling assistance by Allison Fullin

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The King of Reggaetón

By Sara Corbett

• Feb. 5, 2006

A long time ago, before he started draping himself in huge diamond medallions, before flocks of teenage girls began trailing him nearly everywhere, before he had a staff of 15 working day and night on the maintenance of his image, Daddy Yankee had a regular name, which was Raymond Ayala. When he is at home in Puerto Rico, his parents still call him Raymond, as does his older brother Nomar, who works as one of his managers, his wife, Mirredys Gonzalez, who is another manager, and his former neighbors at Villa Kennedy, the run-down San Juan public-housing project where he lived until a few years ago. To just about everybody else, he is Daddy Yankee.

He picked this name for himself back when he was a teenager obsessed with rap music. He watched music videos on MTV and BET and loved what he saw there. He identified with guys like Dr. Dre and Rakim and Big Daddy Kane, the first-generation rappers, even though he was a Spanish speaker who'd never left Puerto Rico and couldn't understand a thing they said. He was, by his own account, a pudgy young kid with no money but possessing a certain brazen faith in his own possibility, a sense that he, too, would outgrow not just his name but his circumstances too. At 13, he rechristened himself Daddy Yankee. In street slang, it means "powerful man." The next year, he started rapping in Spanish, using a friend's four-track recorder, spitting out unrefined lyrics over a speeded-up beat borrowed from Jamaican dancehall reggae.

These days, when Daddy Yankee, who is now 29, performs before throngs of adulatory fans, he will sometimes shout out alternative names for himself, including El Cangri (the chief) and El Rey (the king). All this is meant to emphasize his place at the forefront of reggaetón, a rapidly growing musical genre that mixes Spanish-language hip-hop with the complex rhythms of Caribbean music. With its signature syncopated boom-pa-dum-dum beat and boisterous, often raunchy lyrics -- not to mention the libidinous grind it inspires on the dance floor -- reggaetón has infiltrated nightclubs and radio airwaves with a speed and vigor that has surprised even canny record-company executives. Daddy Yankee's album "Barrio Fino," which was released in 2004, has sold more than 1.6 million copies in the United States, spent 24 weeks on top of Billboard's Latin charts and won Yankee several prizes, including a Latin Grammy. The album's hit single, "Gasolina," became a party anthem that -- akin to Ricky Martin's 1999 hit "Livin' La Vida Loca" -- broke out of the Latin niche and was embraced by masses of clubgoing, booty-shaking Anglo-Americans.

Despite the fact that Americans bought 48 million fewer record albums last year than in 2004, one bright spot for the music industry was Latin music: sales grew by 12 percent, according to Nielsen SoundScan. At least some of that success is owed to reggaetón and by extension to Daddy Yankee, its top-selling act. Reggaetón's biggest hits, which are almost exclusively in Spanish, have found their way into the mix at Top-40 radio stations, playing at health clubs and high-school dances all over the United States.

When I flew to San Juan in November to meet Daddy Yankee, he had just returned to Puerto Rico for the first time in several months, having completed a 16-stop tour of the U.S. and Latin America, plus studio sessions to record new songs to add to "Barrio Fino en Directo," a live version of "Barrio Fino," which would make its debut in mid-December. The early release of his single, "Rompe," a pulsing dance track embroidered with Yankee's trademark staccato rhyming, was climbing to No. 1 on the Latin charts. By late January, it would become the fourth-most-requested video on MTV's decidedly mainstream show "Total Request Live." He had also finished up a frenzied round of corporate deal making with a squad of marketing executives who seemed to have finally grasped Daddy Yankee's exceptional ability to reach and influence the Latino youth market.

"Everybody wants a piece of Yankee," said Lourdes Perez, his chief publicist, as we sat inside an air-conditioned shopping mall on the east side of San Juan, waiting for her charge to surface.

I was third in line for him that day, behind a local newspaper reporter and photographer who had been waiting almost two hours to meet him. Perez, a petite woman wearing high heels and a silk suit, has the unenviable job of marshaling both the artist and the growing number of people who require something from him. Most of her energy was directed toward a relentless speed-dial volley between Yankee's primary handlers -- his brother and his wife -- and his new corporate overlords. Reebok people were flying in to San Juan for a photo session the next day. Interscope Records, which had just signed him to a $20 million, five-album deal, needed Yankee in L.A. for a video shoot in two days.

By the time Daddy Yankee stepped out of his silver BMW sedan into the steamy heat of midday, dressed nattily in a black T-shirt and an impeccably pressed pair of jeans, two pancake-size diamond-crusted "DY" medallions dangling auspiciously from his neck, San Juan's lunch hour was in full swing. Office workers disgorged through the revolving doors of their corporate towers. A flock of uniformed schoolgirls alighted on the corner. Heads swiveled. Traffic slowed. Drivers lowered their windows. At a nearby Pizzeria Uno, a group of waitresses abandoned their tables to rush outside, pens and notepads lofted in anticipation of an autograph.

The first cries came on cue: "Yankeeeee!" And from the schoolgirls, who were now hunting in their bags for their cellphone cameras: "Ohmigod, ohmigod, ohmigod!" A slow grin spread across Daddy Yankee's face. He raised a fist in a dynamic salute to the drivers on the street. He signed somebody's $10 bill. He signed an old lady's shirt. He flung an arm around each one of the schoolgirls, smiling boyishly for their cameras. Posing with male fans, he put on a tough-guy frown, at the same time leveling an index finger in their direction, as if to say, "No, you're the man." The crowd doubled, and then doubled again, like so many dividing cells.

A half-hour later, the only person sulking was the local photographer, who wanted to catch Daddy Yankee in an authentic moment -- standing in front of a graffiti-covered wall, leaning up against a streetlight, anything. But it was not going to happen. The hubbub had simply become too great.

Spend time with Daddy Yankee, and inevitably, as rappers tend to do, he will start talking about "what's real." Being home in Puerto Rico, for example, is real. Reggaetón is real. And most important, he himself is real.

What he means by this is that despite the recent bonanza of five-star hotel stays and glowing reviews of his work, he is still, at heart, the son of a crime-ridden San Juan barrio -- and his music still represents this. It is, of course, the existential quandary of any ghetto-proud artist whose street credibility starts to erode as success carries him further from the streets, but Yankee seems openly pained by the prospect.

With three young children and millions of newly earned dollars, he has moved his family to a roomy house in the beachfront area of Isla Verde, but he also owns the three-room public-housing apartment where he and Mirredys, whom he married when he was 17, lived until 2001. "The first thing I do when I get back from traveling," he said, "is go home, take a shower and drive over to my neighborhood."

We were riding through San Juan in the backseat of his car, which was piloted by his brother Nomar, a soft-spoken and loosely paternal presence. In what seemed to be a regular habit, Yankee had taken off his diamond pendants, which are elaborately scrolled renderings of his initials, made for him by a jeweler in the Bronx, and hung them over the headrest of the front seat. Behind a pair of glinting sunglasses, he stared out the window at the hodgepodge of low-slung pastel bungalows, the dilapidated bodegas and panaderías of Barrio Obrero, the impoverished residential area where he once lived. "The street is my inspiration," he said. "If I got disconnected from this, I'd lose my music."

San Juan is a beautiful, tired city, lush with palm trees and powdery sand beaches. Behemoth cruise ships sit nosed up to its piers; casinos clang and jingle on the waterfront. Old San Juan, colonized by the Spanish in the 1500's, has the same sultry charm as Seville. Beyond it, though, lie neighborhoods of squat, hurricane-resistant houses, whose cheerful paint belies a different reality. Fed by a bountiful drug trade, San Juan's streets are famously violent. Puerto Rico's per capita murder rate in 2004 was more than three times the average of the rest of America. "I can't tell you how many times I've woken up at 3 in the morning to the sound of a mother screaming and crying because she's lost her son," Yankee said. "You learn to be a warrior here. You have no other choice."

Yankee says he carries a bullet lodged in his right thigh, a souvenir of a gang-related shooting in a caserió -- a housing project -- when he was 16. He was leaving the apartment of DJ Playero, one of the first producers of reggaetón. It was, he claims, a case of mistaken identity. He spent the next six months in bed; it was a year before he could walk. That hiatus from street life was what persuaded him that he should focus full time on making music. He went to college as well, earning an associate's degree in accounting in 1998, in order to help himself better navigate the music business. "I thank God every day for that bullet," he said.

At times, Daddy Yankee can sound like an evangelist, sermonizing about the plight of the urban underclass, pointing out both the richness and depravity of life on his native island. One of the most powerful tracks on "Barrio Fino" is "Corazones," a ferociously delivered bit of protest poetry that laments the "spirit of death" in Puerto Rico, implores politicians to budget more money for teachers and proposes a gang truce. (Privately, he acknowledges that his hopes are unrealistic but nonetheless worth voicing.) Yankee's ultimate power, however, lies in the ability to switch between agendas. "Corazones" is preceded on the album by "Dale Caliente" (which translates to "Give It to Me Hot"), a jumpy, insistent tune in which Yankee jubilantly addresses the ladies, directing them in Spanish to "move those butt cheeks till the earth trembles."

Yankee's music -- and indeed a substantial amount of reggaetón -- is built to fuel that earth-trembling, hormonal energy of nightclubs, parties and concerts. In San Juan, club attire for women is normally high heels, bare legs and just enough spandex to cover the parts that need covering. The dance style most in vogue is a graphic, butt-to-crotch meld referred to as "el perreo" -- the doggie. And reggaetón lyrics, even when laced with social consciousness about race and class and life in the ghetto, are often a call, specifically addressed to female clubgoers, for more dancing and less clothing.

Yankee passes little time in clubs these days, saying that he prefers to spend nights in his recording studio with friends or to be with his wife and children -- ages 7, 9 and 11. He does not drink or use drugs, saying that alcohol was "an issue" in his house while he was growing up. By all accounts, he is a tireless worker and a shrewd businessman, having started his own record label, El Cartel, when he was just 21. He put out four albums this way -- overseeing everything from manufacturing to marketing himself. Now that he has help from a big label, his associates say he is fixated on pushing his music onto the world stage. "Two years ago he couldn't hold a conversation in English," says Edwin Prado, Yankee's San Juan-based attorney and business manager. "But the kid is disciplined. He learned it quick."

According to Prado, Yankee asks him to practice media interviews in English during the three-hour-plus flights they regularly take between New York and San Juan. Perhaps as a result, Yankee comes off as polite, articulate and polished to a high gloss. He is careful not to slag any of his fellow reggaetón artists, even though there is a widely reported rivalry between Yankee and the almost-as-successful 26-year-old rapper Don Omar. ("I've been through a lot of beef with other singers," Yankee told me, "but it's all verbal.") He speaks warmly of his parents, who are now divorced, describing his father, a one-time percussionist for some of Puerto Rico's best-known salsa acts, as a "humble dude" and his mother, a manicurist responsible for raising the family's four children, as loving but "very strict."

Depending on what the moment calls for, Yankee can pout and sneer with thuggish authority, and he can work a certain coltish charm. He speaks to women in a buttery, lilting voice and will impulsively reach out to squeeze your arm in order to emphasize a point. "You feel me, mama?" he will say, deeply earnest. And it is hard not to. With men -- even the square, marketing types with whom he now regularly deals -- Yankee adeptly goes through the motions of bad-boy camaraderie, punching fists and amiably yo-what-upping with each new acquaintance. "I know how to read people,' " he said. "When you grow up in a rough environment, you have to have a sixth sense."

Like any good rapper, Daddy Yankee practices a stylized brand of showmanship, wielded most dramatically when he is performing live. During his tour of the U.S. last year, he arrived onstage dressed in a pristine white suit and ermine robe, perched on a golden throne. Last February, performing at a televised Latin music awards ceremony, he glided from the rafters in a tricked-out, floating Lamborghini, peering down at the audience and a waiting line of scantily clad female dancers, shouting something that could be construed as a rallying cry for Latino power. "We're ready!" he called emphatically, his head bobbing to an intensifying beat. "We're ready!"

Reggaetón is not for everyone. Its hammering snare drums and nasal melodies may seem wearyingly one-dimensional, especially for those who don't speak Spanish. At its best, however, the music blends a rich mix of cultures. Here, the verbal wizardry of hip-hop plays off a variety of traditional tropical sounds, including salsa, merengue, Dominican bachata and even bomba and plena, the heavily percussive forms of music brought to Puerto Rico by African slaves working on sugar plantations and their descendants. "It sounds completely different from anything else," says Leila Cobo, Billboard magazine's bureau chief for Latin music, citing reggaetón's distinctive and highly danceable rhythm. "You cannot mistake it for hip-hop, and you certainly can't mistake it for pop."

It was another group of workers, Jamaicans living in Panama, who introduced reggae and, later, its quick-tempoed cousin, dancehall reggae, to the Latin world. In 1991, a Panamanian singer named El General took dancehall's rollicking beat and added Spanish lyrics, which in turn sparked excitement in Puerto Rico. As American hip-hop drifted down from the north and dancehall floated up from the south, the two genres became the music of choice at San Juan's nightclubs and house parties, even as Puerto Rican radio remained devoted to salsa, pop and merengue.

At the time, Daddy Yankee was among a handful of aspiring young rappers collaborating regularly with DJ Playero, whom he refers to as the godfather of reggaetón. Working with low-tech equipment in a home studio, Playero created a steady flow of mix-tape compilations by local artists, which were then sold from apartments and car trunks, further fueling the underground party circuit. "We were doing hip-hop and dancehall, but it wasn't ours," Yankee recalled. "Then we started to play both beats at once. We took dancehall and hip-hop and mixed it in the middle. I knew we had something. I thought, This sound is Puerto Rican sound."

The earliest incarnation of that sound was a demonically fast drumbeat overlaid with urgent, often incendiary rap. Raquel Z. Rivera, who teaches sociology at Tufts University and is the author of "New York Ricans From the Hip Hop Zone," is at work on a book about reggaetón. She describes early reggaetón lyrics as "not just explicit, but violently explicit" and "extremely misogynistic" and also "wildly popular" in the barrios. Daddy Yankee simply describes it all as "real." He remembers bringing cassettes to radio stations. "I'd say, 'Play this, play this.' It's what's being played in the street, it's what's real, but they didn't pay any attention."

Eventually, reggaetón compilations began selling more formally in stores, though not without controversy. In February 1995, acting on charges that the music's lyrics violated local obscenity laws, police officers raided six record stores around San Juan, confiscating hundreds of CD's and cassettes. In 2001, a senator in the island's Legislature agitated loudly but unsuccessfully for a ban on reggaetón, claiming that it incited violence and was degrading to women. The debate only further stoked reggaetón's outlaw popularity among urban kids. "We were speaking about drugs, about wars on the streets, wars in the government," Yankee said. "We were using bad words, but that was real. It was how we talked. In reggaetón, you say what you want. That's the essence of the movement."

For the next several years, reggaetón continued to fulminate largely below the surface. "It was like a cult of teenagers buying the music," says Eddie Fernandez, vice president for U.S. Latin and Latin America at Sony/ATV Music Publishing. "Reggaetón artists had no radio airplay at all. The major record guys and people in their 30's never paid attention to them. They said, 'Eh, this is nothing.' "

Along the way, reggaetón started to travel, arriving in places like New York, Orlando and Boston in the suitcases of itinerant Puerto Ricans. "Suddenly it was coming from boom boxes, from cars, from homes," recalls Rivera, who is based in New York. "Little by little, it started spreading, first to Puerto Ricans living in New York and then to Dominicans." The music industry began to catch on only slowly. In 2002, Universal Music bought distribution rights to a number of reggaetón artists' works, including Daddy Yankee's, from a Puerto Rican label called VI Music. Various D.J.'s in the U.S. further helped to cross-pollinate reggaetón and hip-hop by remixing hits from artists like Jennifer Lopez and LL Cool J with the reggaetón beat.

And then there was "Gasolina." Written in 2003 by Daddy Yankee and fellow reggaetón artist Eddie Dee, with help from reggaetón's most dynamic producers, a young duo known as Luny Tunes, "Gasolina" created its own weather. The song is both imperious and hollow, a pitch-perfect party tune involving a call and response between Yankee and a cloying female chorus -- one that has now been reproduced by keyed-up nightclub crowds all over the world. The lyrics describe a girl who "loves gasoline" -- le gusta la gasolina -- which Yankee says is a Puerto Rican way of describing a girl who likes to live a life of "cruising around in cars." The song, which has a popular remix version featuring the mainland rappers Pitbull, Lil Jon and N.O.R.E., involves women calling for more gasoline and the men boasting about how they'll give it to them. Read this however you like.

"That song changed everything," Cobo, the Billboard editor, says. "If it weren't for 'Gasolina,' the mainstream wouldn't have ever heard about reggaetón."

Like hip-hop before it, reggaetón has evolved over time to be more palatable to the masses. The rhythms have slowed, and in deference to the requirements for radio play, lyrics tend to be cleaner than they once were, though they remain stacked with double-entendres about sex and partying. Puerto Rico has two radio stations devoted exclusively to reggaetón, and reggaetón artists are now regularly asked to perform at political rallies in Puerto Rico. "The same politicians who were shunning reggaetón are now campaigning to it," Rivera says. "It's gotten that popular." Daddy Yankee, in particular, has become an icon of Puerto Rican pride. "Until maybe two years ago, the older generations were not claiming reggaetón at all," Rivera says. "It's only very recently that there seems to be a consensus that reggaetón represents Puerto Ricans properly to the rest of the world."

The music's growth on mainland America has contributed to a mini-revolution in radio programming. Last year, Clear Channel switched four of its English-language stations in major markets like Houston and Miami to a Hispanic-urban format called Hurban, featuring reggaetón and Latin hip-hop. Univision Radio similarly has converted seven of its Spanish-language stations from more traditional Latin music like merengue and salsa to a reggaetón-driven format known as La Kalle. Reggaetón's kinship with hip-hop seems to have helped it jump many of the regional fences traditionally dividing the Latin music market, where in the U.S., Mexican-derived music has long ruled the West Coast and Caribbean music has dominated the East. "It's unified the Latin masses," Daddy Yankee told me, adding that he believes reggaetón is especially popular with second-generation immigrants, even those who don't speak Spanish. "The music makes them feel Latino," he said. "It's in their heart."

The recording industry has scrambled to keep pace with the boom, dispensing representatives to prowl San Juan nightclubs in search of new talent and speedily inventing labels that cater to the young Hurbanites. In the last year, Universal Music has created a Latin hip-hop label called Machete Music; Wu-Tang Records unveiled Wu-Tang Latino; P. Diddy started Bad Boy Latino; and the hip-hop impresario Jay-Z joined with Def Jam Records to create Roc La Familia. It's hard to question the wisdom of these investments: census figures show that the Hispanic population is growing at three times the rate of the overall U.S. population and more than half of the 41 million Latinos living in the United States are under age 29.

When I met with Prado, Daddy Yankee's voluble business manager and chief corporate deal maker, his outlook was just shy of gleeful. "The numbers are talking," he said, as multiple cellphones rang from the pockets of his suit. "The U.S. is becoming a Spanish-speaking nation." In other words, these are good days to be making money from someone who makes money by touching the hearts of Latino kids.

There is a corresponding, told-you-so swagger to be found among Puerto Rico's collection of rising stars -- reggaetón artists like Tego Calderón, Don Omar and Wisin y Yandel, among others -- who are now doing things like touring Japan and taking meetings with pinstriped corporate people. Their vindication is rich but also paradoxical: in creating a platform for what Yankee refers to as "poor people's music," they've allowed the rich people in. It's the same trajectory that gangsta rappers of the past once traveled, a rite of initiation from the street world into the sales world that can be exhilarating, soul-killing and insanely lucrative.

Daddy Yankee remains, for the moment, the best-selling artist of the bunch. He is quick to correct the impression that he or any of his compatriots are overnight sensations. "We've been doing this for more than 10 years," he told me. "Even though we didn't have the tools or the resources to make music, we did it. We made something new." There was a territorial edge to his pride, one that hinted that he was aware of the opportunism that now surrounded him. "It's our music," he said. "It's our movement."

We were just pulling into Villa Kennedy, Yankee's old caserió. Nomar parked the BMW on the grass, and Yankee climbed out. Tucked away from the main street, Villa Kennedy is a collection of three-story apartment buildings set next to an overgrown field about 10 miles east of the city center. A breeze sifted through the almond trees. Two scruffy chickens pecked their way across the yard. Yankee seemed palpably to relax, taking a seat on a low wall as word of his arrival spread. Children coasted over on their bikes. A woman opened her window to shout hello.

For the next hour, a small group of people sat with him in the late-day sun, chattering at a high pitch, doling out advice and recollections: invest your money well. Don't get spoiled. We remember you when you were gordito -- a little fat boy. Daddy Yankee laughed and nodded his head. Earlier in the day, he told me that Puerto Ricans see him as a mirror to themselves and to the island. His success, in other words, was theirs.

"In hip-hop, when you become a big star, it's like you don't belong in the 'hood anymore," he said. "But here, it's the opposite. They're proud." He also offered a bold declaration about his future: "I want to be a true-born leader who is going to take his whole country to a high level without sacrificing who we are." However pretentious or possibly naïve the thought may have been, it was also utterly sincere. It was, as Yankee might say, real.

Another apartment door opened then. An elderly man dressed in work clothes peered down from the porch and waved enthusiastically. "Mira," the man called to some unseen person behind him in the cool shadows, "vuelva Raymond!" Look, Raymond is back!

the following day I met the sneaker version of Daddy Yankee. It's a nice shoe, more lifestyle wear than athletic wear, and carefully designed to represent Yankee as best as a stitched piece of leather can represent anybody. The sneaker's upper has a box-weave pattern, inspired by the Caribbean straw hat, I was told, and the sock liner -- the foamy insert that covers the sole -- has a map of Latin America sketched over it.

"It's clean; it's classy; it's sophisticated," a Reebok product manager was telling Yankee, as the reggaetón star examined prototypes of the sneaker in different colors. We were in a rented photo studio in Old San Juan. Yankee had three publicists on hand that day, in addition to Nomar and Prado. Four people had flown in from Reebok's headquarters in Massachusetts, as well as a photographer and two assistants.

Yankee seemed pleased with his sneaker, and also with the complete "DY" apparel line Reebok intends to introduce in the spring. The proposed copy for the print advertising campaign was "For the people." Yankee nodded his head as this was explained to him. "The concept is good, powerful," he said. "The message is there: I'm representing you."

The contract with Reebok was brand new. In fact, several of the Reebok reps confessed they'd known virtually nothing of Daddy Yankee before he signed with the company. "We'd heard he was a key player in the Hispanic market," Lisa Cardoso said with a shrug. Cardoso is Reebok's lifestyle-and-entertainment marketing manager, in charge of wrangling the company's celebrity endorsers, including the rappers Jay-Z, Nelly and 50 Cent. Yankee could meet them all, she said, at the N.B.A. All-Star weekend in Houston. He should go, she told his publicist Lourdes Perez as they huddled in a conference. Reebok could arrange a performance. Yankee could make what she called "good connections."

With Interscope planning to release Daddy Yankee's first major-label album later this year, the pressure was already beginning to mount. Connections mattered. Celebrity mattered. Its success will likely be viewed as a measure of reggaetón's staying power, its ability to cross over into a larger market. "The fact that Yankee signed with a mainstream label indicates that a lot of people -- not just him -- think he's got a possibility beyond Latin," says Leila Cobo of Billboard. According to Prado, the new album, titled "El Cartel," will have Yankee rapping in a mix of Spanish and English, though he noted the delicate cultural line his client must walk. "It's important to get his message into English," Prado said, "but he can't lose what he's about."

As the photo shoot in San Juan got under way, Daddy Yankee donned a freshly manufactured midnight blue jacket with royal blue trim and a "DY" logo embroidered over the heart. He wore dark sunglasses and his diamond "DY" pendants, plus two diamond bracelets and an enormous pinky ring. The photographer set him up against a blinding white backdrop and began to shoot.

Yankee knew what to do. He threw back his shoulders, raised his chin proudly and stared down the camera, his lips set in a firm line. "Yeah, that's hot," said the photographer, from behind the lens. "Look at the clothes," he added. And when Yankee gingerly touched a finger to the logo on his jacket, the shutter clicked even more furiously.

Between takes, everybody turned away -- the photo team to check the images as they appeared on a laptop, the publicists to resume work on their cellphones, the Reebok people to confer about marketing plans. Yankee's expression slackened. Behind him was a scrim of white paper, a big blank expanse that was just a holding place for what would be the advertisement's real backdrop -- some gritty-looking, Latin-looking street location to be Photoshopped in later.

An assistant handed him a sneaker, and the shooting started up again. Yankee lifted the shoe to eye level and gave it a hard, meaningful look. "Yeah," the photographer encouraged, "hold that." Then, abruptly, they all turned away again, examining the image on the computer screen, back on the phone, back in conference. Only Daddy Yankee stood there, beneath the glaring lights, still holding his pose.

Sara Corbett is a contributing writer for the magazine.

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