Dive into the reaches of YouTube and you’ll find a video of Daddy Yankee performing live in his late teens, wearing a silver zip-up windbreaker and crawling caterpillar mustache. It was 1996 and the future global ambassador of reggaeton freestyled a cappella in front of a crowd of hundreds. He showed off a breathless flow with touches of Patois intonation, a signature of the time, when the genre “underground” – a precursor to reggaeton – was thriving. The DJ dropped a beat, chopped drum breaks and syncopated dembow riddims. Yankee kept it up effortlessly, swinging the hyperspeed raps that would make him a superstar in the next decade.
Cherub-cheeked and about 19, Daddy Yankee grew into a reggaeton king, pop star, and tycoon, helping to transform a street noise into an industrial cash cow. In 2004, he announced his rise to the mainstream with a strategic and simple opening line: “Who is this? Papa Yan-kee!” A little over a decade later, he played the acoustic guitar and brought the popeton beat of “Despacito” to irritating, international ubiquity.
But after a career spanning 32 years, is it time for Yankee to rest on its laurels? In a sentimental video posted on March 20, the Big Boss announced his retirement from the music industry. There’s one more round of victory: a final tour and an impeccably titled album, ‘Legendaddy’.
Retirement albums can be tricky. Some artists misrepresent recent trends in an effort to reproduce the aesthetics of a younger generation; others repeat the tricks that made them famous in the first place; the most successful dare to expose their souls and create new intimacy with listeners.
Yankee, 45, has never really been one for deep personal vulnerability. However, he was always honest about his childhood at 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, spreading their experiments on mixtapes in the early s’ 90. When Yankee was 16, a bullet lodged in his right leg, a souvenir from a crossfire outside Playero’s studio one afternoon. It forced him into more than a year of recovery, closing the door on his major league baseball aspirations and focusing his energies on music.
As underground and later reggaeton expanded, Yankee refined the art of fusing sex and bombast in songs. Using street swagger and dirty talk, he used his breakneck rap flows in carnal dance floor anthems, such as 2002’s “Latigazo” or his 2004 hit “Gasolina”. These became the songs that taught an entire diaspora about sex and the ecstasy of a perreo. sucio, the kind of grinding where denim dye and sweat are exchanged with a dance partner.
There were sporadic moments of social commentary in Yankee’s music, such as on the blockbuster theatrical album ‘Barrio Fino’. But after “Gasolina” flooded the Anglo mainstream, his celebrity grew and he traded his lecherous playboy image for that of a wealthy mogul: In 2005 alone, he signed a brand partnership with Reebok to design sneakers, apparel, and accessories; agreed to model for Sean Jean’s spring collection; landed an endorsement contract with Pepsi; and signed a $20 million, five-album deal with Interscope Records.
As Yankee settled into his role as a reggaeton capitalist, his success in the mid-’00s also felt like confirmation to a generation of young people from the Caribbean diaspora. Reggaeton was the first music that was completely ours – fresh, raw, exciting, sensual. It brought us closer to the islands that produced us, and towards a wistful dream of wholeness rather than constant loss.
Yankee released a spate of albums in the early and mid-2010s, but many of them lacked dimension and verve and relied on unimaginative commercial tropes. Around 2016, he started dabbling with two ascendant sounds: the first apex of EDM-reggaeton fusions and the nascent genre of Latin trap, in which he became a sought-after guest. Both allowed him to stay in the spotlight, embrace his image as an elder statesman, and avoid competition with a new wave of artists who refreshed the movement with sentimentality and grit.
For ‘Legendaddy’, his first solo album in ten years, El Cangri has inventoried the sounds and styles that shaped his career: self-mythologizing rap, perreo, EDM and pauson. The most dynamic moments come when Yankee reaches for the magic of the past – whether indulging in boastful hubris or prompting listeners to muse on the dance floor. “Uno Quitao y Otro Puesto” is a bitingly effective explosion of late career stature, complete with gunshot accents à la “Sácala.” On “Enchuletiao” Yankee doesn’t rap, he barks a stream of bars about his unparalleled eminence in the genre, delivered by 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, when I’ve been in all ages?” It’s a reminder of his engineering prowess – he hasn’t sounded so electric and so wonderfully abrasive in years.
With their stadium-sized trumpets and lively piano lines, “Rumbatón” and “El Abusador del Abusador” are exciting, nostalgic recalls to the salsa-reggae ton fusions of the mid-’00s (appropriately Luny of the duo Luny Tunes produced “Rumbatón”). “Remix” and “Bloke” are classic reggaeton romps, tapping into the kinds of sexual fantasies and lustful exchanges that once made the sound so irresistible; the first even includes a reference to the Big Boss’ 2007 song “Impacto.”
Still, much 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” almost sound like they were designed for Spotify’s “Viva”. Latino” playlist. “Pasatiempo”, featuring Myke Towers, ends up mainly due to the interpolation of Robyn S’s “Show Me Love”. Sampling universally loved bangers is a method Yankee was afraid to use in the past (i.e. “Con Calma”), and it works here again.
“Legendaddy” also has some glaring missteps: two EDM mergers, the globally popular style that has recently taken hold on the Latin charts. “Bombón”, featuring Lil Jon and the dembow visionary El Alfa, is virtually inaudible – college spring break music, complete with “Yeah!” ad-libs from a bygone era. Dominated by its Pitbull feature, “Hot” is essentially a caricature of Miami nightclub fare.
Yankee leaves room for a refreshing moment of adventure with “Agua”. The song, a collaboration with Nile Rodgers and reggaeton star Rauw Alejandro, is sparkling disco pop gloss, complete with groovy guitar riffs from the Chic legend.
As a farewell album, “Legendaddy” honors all styles of Yankee’s trajectory and highlights the superpower that has enabled him to survive as a senior figure in a young artist’s game: flexibility. And in that way, the album also reflects the history of reggaeton itself: a sound now unrecognizable from its political, grass-roots beginnings, and one whose history implies constant transformation.
There’s always a chance Yankee will return on some sort of comeback tour, as many hip-hop giants have done after they retire. Yankee got his flowers while he was still around, and his indelible impact cannot be underestimated. But “Legendaddy” also speaks volumes about what reggaeton needs more of right now: fresh blood, unorthodox aesthetics, and narrative world builders looking to inject the genre with the euphoria, fireworks, and narrative depth the movement has promised since its inception.