Daddy Yankee Forever: A Reggaeton Legend Goes Out on Top

Music

The 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.

The people who arrive early span several generations, standing in for every era of Daddy Yankee’s three-decade career. Middle-aged dads in baseball caps walk toward the concert gates, perhaps nostalgic for their college years, when “Gasolina” caught fire everywhere, followed by reggaeton classics such as “Rompe,” “Lo Que Pasó, Pasó,” and more. Younger millennials are also in the crowd, and many of them probably remember Daddy Yankee’s ubiquity after “Despacito” took over the airwaves in 2017. There are glammed-up girls, flipping through the same phones they might have used to post his near-constant TikTok dance challenges for recent songs like “Bombón.” The arena fills up with kids, tias with dyed hair, groups of friends who have flown in from other countries. No matter where they traveled from or when they became fans, they’re counting down to see the Puerto Rican veteran, who announced his retirement in March, perform at his last tour ever.

A hidden gate tucked near one corner of the 20,000-person venue leads backstage, where there’s a sense of nervy contained chaos in the air. Daddy Yankee has been traveling on a tour bus behind a caravan of 14 trucks stocked with the stage equipment required for a production as big as the one he has planned. Earlier in the day, all the vehicles snaked down packed Nevada highways to the arena, which has transformed into a mini village dedicated to showtime. In one room, two seamstresses are bent over twin sewing machines, adjusting the dozens of outfits that dancers will switch out of throughout the night. In another area, Daddy Yankee’s personal cameramen are fiddling with lenses and rigs, while elsewhere, two physical therapists and a doctor, all from Puerto Rico, are ready to check out anyone whose muscles might be cramping before the curtain rises. I cross paths with a groomer, a barber, a road manager, and a wardrobe assistant before finally arriving at a wide doorway.

Photograph by Carlos Jaramillo. Look by YSL

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.”

Carlos Jaramillo for Rolling Stone. Glasses by Gucci. Jacket and Necklace: Vintage Versace from Pechuga Vintage. Shirt by Versace. Trousers by Calvin Klein.

An hour later, he starts moving toward the stage. The audience screams as a giant blue clock begins counting down the seconds until the show starts. When it finally hits zero, the climactic beat of “Campeón,” from his new album, starts. Ayala steps out wearing sunglasses, his movements steely and full of swagger. He roars out the beginning of the song, his voice charged and packed with power — totally different from his reserved composure backstage. The crowd roars back, aware they’re watching a victory lap in real time.

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.

Reggaeton didn’t have a name when Ayala started pursuing music more seriously in the early Nineties, but Puerto Rico’s underground scene was already flourishing. DJs on the island had started fusing all kinds of sounds — dancehall riddims from Jamaica, reggae en español that had thrived in Panama, New York hip-hop, and electronic music blossoming in nocturnal spaces across the U.S. — and morphing them into a distinctly Puerto Rican style. “It was all of these influences, like if you put dancehall, reggae, reggae en español, rap, house music, salsa, bachata, and vallenato in a blender,” Ayala says. Before long, he was gaining recognition in the neighborhood, appearing on homemade tracks by pioneers like DJ Playero and DJ Nelson — and it got him noticed as a teen prodigy with impeccable flow. (Though it’s hard to say who exactly coined the phrase, DJ Playero has said he thinks it might have been Daddy Yankee who baptized the genre.) “I never forced anything,” Ayala says. “From the minute I opened my mouth, it went viral.”

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.”

The timing was just right for Ayala, who was eager to make even bigger moves in his career. He started plotting a game-changing album, called Barrio Fino, which would capture the sound he’d been refining for himself, and he knew it needed a centerpiece. Saldaña had been tinkering with the original production for “Cójela Que Va Sin Jockey,” creating a new track that preserved the song’s uptempo verses but added striking, hydraulic-inspired details. “I added [those sounds of] cars and motors and brakes,” Saldaña says. “The idea was that it was fast and had a lot of speed.”

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.”

Daddy Yankee at the 2005 Billboard Latin Music Awards in Miami, at the height of his first commercial breakthrough.

John Parra/WireImage

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.” 

Despite how big “Gasolina” was, reggaeton still struggled initially to get the respect it deserved. Jesús Triviño, now senior director of global Latin culture and content at Tidal, was a journalist covering the hip-hop and Latin-music industry at the time, and one of the first people stateside who ever interviewed Ayala. “I remember on the Spanish-language side, Univision, Telemundo, those types of outlets, they weren’t really touching it because they saw it as [coming] from the streets: ‘It’s not pop, it’s not squeaky-clean. This isn’t marketable, we can’t sell ads to this,’” he recalls. “Then, on the English side, I remember personally pitching a lot of reggaeton stories to these hip-hop magazines, and very few were accepted. A lot of them were like, ‘That’s not hip-hop.’” 

“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.

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.

Ayala credits much of his success through the years to his decision to run his business through El Cartel Records. “People from Latin rock, pop, salsa, and merengue worlds would call: ‘Yankee, how did you do it? We’ve been trying, but we’ve been unable to make that kind of money.’ And I’d always say, ‘It’s because I’m my own boss.’” He’s struck distribution deals with Sony and Interscope to give his music more global reach, but he’s always been the one in charge of his catalog. 

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.’” 

Plus, he felt — perhaps more than ever in his career — reassured by the wild new heights that reggaeton had reached. Many people point out that Ayala has been able to keep his momentum going for so long because he’s kept an eye on younger artists, often inviting them to collaborate. Now, many of the rising stars he’d gotten to know had become full-blown sensations. “It was always my goal to carry the banner and lead, and then have other people keep going,” he says. “Everything that’s happening with Bad Bunny, incredible. What’s happening with Karol G, incredible, with Sech, with Rauw Alejandro, with Myke Towers. There’s the new kids and also the new veterans, like Balvin, Maluma, Ozuna, Anuel AA. They’ve done a remarkable job.” The music was in a good place. He started making plans for his last album.

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. 

Usually, Ayala won in the end. “He’s just fucking naturally good at everything,” Salinas continues with a laugh. “I was like, ‘God, you shoot a basketball, play Street Fighter. What do you suck at, bro?’”

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.

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.”

We talk again over Zoom early in September, just as he’s settling into a hotel in Montreal. At about 8 p.m., his Zoom username pops on my screen — Sikiri, the moniker he gave the bobble-headed Animoji character from his “Con Calma” video. Ayala appears within seconds, wearing sunglasses and a black skullcap. He’s just finished working out, and he’s still preserving his voice. “You’re the first person I’ve talked to in 15 hours!” he says with a slightly raspy laugh.

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.”

Production Credits

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.

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