Daddy Yankee, the world’s first reggaeton star, steps aside

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Dive into the corners of YouTube, and you’ll find a video of Daddy Yankee performing live in his late teens, wearing a silver zippered windbreaker and a trailing caterpillar mustache. It was 1996, and the future global reggaeton ambassador was freestyling a cappella in front of a crowd of hundreds. He displayed a breathless flow with touches of patois intonation, a signature of the time, when the “underground” genre – ancestor of reggaeton – was flourishing. The DJ dropped a beat, cutting drum breaks and syncopated dembow riddims. Yankee carried on effortlessly, brandishing the hyperspeed raps that would make him a superstar in the next decade.

Daddy Yankee, cherub-cheeked and around 19 years old, became a reggaeton kingpin, pop star and mogul, helping turn a street sound into an industry cash cow. In 2004, he announced his rise into the mainstream with a strategic and simple opening statement: “Who is this? Papa Yan-kee! A little over a decade later, he straddled the acoustic guitars and liquefied the popeton rhythm of “Despacito” in a vexing international ubiquity.

But after 32 years of career, is it time for Yankee to rest on its laurels? In a sentimental video released on March 20, the Big Boss announced his retirement from the music industry. There remains a victory lap: a final tour and an album with an impeccable title, “Legendaddy”.

Retirement albums can be tricky. Some artists mistakenly surf on recent trends to try to reproduce the aesthetics of a younger generation; others rehash the tricks that made them famous in the first place; the most successful ones dare to bare themselves and create a new intimacy with the listeners.

Yankee, 45, has never really been one to be deeply vulnerable. He was, however, always honest about his youth in the Villa Kennedy caseríos, or housing projects, in San Juan, where he and DJ Playero, another reggaeton pioneer, tinkered with reggae en español and freestyling, and broadcast their experiences on mixtapes in the early 90s. When Yankee was 16, a bullet lodged in his right leg, a memory of a crossfire outside Playero’s studio one afternoon. It forced him into over a year of recuperation, closed the door on his major league baseball ambitions, and refocused his energies on music.

As underground, then reggaeton, extended, Yankee has honed the art of fusing sex and emphasis in song. Harnessing street bluster and dirty talk, he leveraged his frenzied rap flows into carnal dancefloor anthems, like 2002’s “Latigazo” or his 2004 hit “Gasolina.” the songs that taught an entire diaspora about sex and the ecstasy of a perreo sucio, the kind of grind that involves swapping denim dye and sweat with a dance partner.

There have been sporadic moments of social commentary in Yankee’s music, such as on the hit album “Barrio Fino.” But after “Gasolina” engulfed the Anglo-Saxon mainstream, his stardom grew and he traded his image as a lustful playboy for that of a wealthy tycoon: in 2005 alone, he signed a brand partnership with Reebok to design sneakers, apparel and accessories; Agreed model for Sean Jean’s spring collection; landed an endorsement deal with Pepsi; and signed a $20 million, five album OK with Interscope Records.

As Yankee settled into his role as a reggaeton capitalist, his success in the mid-2000s also felt like an affirmation for a generation of young people in the Caribbean diaspora. Reggaeton was the first music that belonged entirely to us – fresh, raw, uplifting, sensual. It brought us closer to the islands that gave birth to us, moving us to a melancholic dream of wholeness instead of constant loss.

In the early and mid-2010s, Yankee released a string of albums, but many of them lacked dimension and verve, relying on unimaginative commercial tropes. Around 2016, he began performing with two ascending sounds: the early crest of EDM-reggaeton fusions and the burgeoning genre of Latin trap, in which he became an in-demand guest star. Both allowed him to stay in the spotlight, embrace his image as an aging statesman, and avoid competing with a new wave of artists who were refreshing the movement with sentimentality and courage.

For “Legendaddy”, his first solo album in a decade, El Cangri inventoried the sounds and styles that defined his career: self-mythologized rap, perreo, EDM and popeton. The most dynamic moments come when Yankee reaches for the magic of the past – whether it’s indulging in boastful hubris or summoning listeners into dancefloor reverie. “Uno Quitao y Otro Puesto” is a corrosively effective outburst of career-ending postures, with accents of gunfire a la “Sácala.” On “Enchuletiao,” Yankee doesn’t rap, he barks a stream of bars about his genre-unmatched eminence, delivered through gritted teeth. “¿Qué tú me va’ a enseñar, si yo he esta’o en to’a las era’?” he says. “What are you going to teach me, if I have been in all ages?” It’s a reminder of his technical skills – he hasn’t sounded so electric, so delightfully abrasive in years.

With their stadium-sized trumpets and vibrant piano lines, “Rumbatón” and “El Abusador del Abusador” are thrilling, nostalgic reminders of the salsa-reggaeton fusions of the mid-2000s (aptly, Luny du duo Luny Tunes produced “Rumbatón”). “Remix” and “Bloke” are classic reggaeton romps, tapping into the kind of sexual fantasies and salacious exchanges that once made the sound so irresistible; the former even includes a reference to Big Boss’ 2007 track “Impacto.”

Still, a good chunk of the songs follow prosaic, predictable pop formats: “Para Siempre” weaves acoustic guitar textures into a bland, mid-tempo popeton ballad, while “La Ola” and “Zona del Perreo” sound almost as if they were made for Spotify’s “Viva Latino” playlist. “Pasatiempo,” featuring Myke Towers, lands primarily due to its interpolation of Robyn S’s “Show Me Love.” i.e. “Con Calma”), and it works again.

“Legendaddy” also has some glaring missteps: two EDM fusions, the globally popular style that recently had a grip on the Latin charts. “Bombón,” featuring Lil Jon and dembow visionary El Alfa, is virtually unlistenable — college spring music, with “Yeah!” ad-libs from a bygone era. “Hot,” which is dominated by its Pitbull feature, is essentially a caricature of Miami nightclub fare.

Yankee leaves room for a refreshingly adventurous moment with “Agua.” The track, a collaboration with Nile Rodgers and reggaeton star Rauw Alejandro, is brilliant, sparkling disco pop, complete with groovy guitar riffs from the Chic legend.

As a farewell album, “Legendaddy” honors every style of Yankee’s trajectory, highlighting the superpower that allowed him to survive as a figurehead in a young artist’s game: flexibility. And in this way, the album also reflects the history of reggaeton itself: a sound now unrecognizable from its political and popular beginnings, and whose history involves constant transformation.

There’s always a chance that Yankee will return on some sort of comeback tour, as many hip-hop giants have done after retiring. Yankee got his flowers while he was still around, and his indelible impact cannot be underestimated. But “Legendaddy” also says a lot about what reggaeton needs most right now: fresh blood, an unorthodox aesthetic, and storytellers looking to inject the genre with euphoria, fireworks and the narrative depth that the movement has promised since its inception.

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