The Guide to Getting Into Daddy Yankee, One of the Greatest Rappers Ever

Whether over a dancehall riddim, a dembow loop, or a boom bap beat, Daddy Yankee is truly a G.O.A.T. emcee—full stop, no Spanish-language consideration or otherwise marginalizing categorization needed.

When “Gasolina” hit stateside in 2004, nothing would ever be the same. Distinct from the glamorous and popwise Latin Explosion whose shellings flanked the millennium marker, its aggressive arpeggiation and forceful use of the dembow rhythm by the Luny Tunes duo rattled bassbins across cities and gave American audiences an uncompromising taste of what Puerto Rico had been cooking up for over a decade. The vocals, urgent and shouty, played with automotive metaphor in the age of The Fast And The Furious. While plenty of young Latinx listeners were already quite familiar with the urban movement and the artists operating therein, the coronation of Daddy Yankee as reggaeton’s first global superstar began then.


Even if you’re more or less unfamiliar with the intricacies, rivalries, and touchpoints of música urbana, the convenient catch-all used to describe a variety of Spanish-language hip-hop forms, you no doubt know his name. The Río Piedras native boasts a staggering 63 singles that appeared on Billboard Hot Latin Songs chart in the last decade and a half, ten of which crossed over to the Hot 100. Among these are reggaeton classics “Impacto” and “Rompe” as well as more recent hits like “Dura” and the chart-topping phenomenon “Despacito,” all of which contain either his dextrous flow, catchy hooks, or both.

And still, you’ll never hear Yankee mentioned when people talk about the G.O.A.T., rap’s most tiresome debate. Ludicrously excluded over the years from the discussion, which plays out just about every other week on social media nowadays, his tenure in hip-hop runs at least as long as those of perennial candidates Jay-Z and Nas. Debuting in 1992 on the immensely important Playero 34 mixtape, that formal introduction on the mic put him in the same storied freshman class as countless Golden Age greats, the only difference being that Yankee operated out of San Juan instead of New York or Los Angeles. Even as hip-hop gradually warmed on a national scale to including previously underrated and oft ignored regional scenes, especially those in the American South, reggaeton trailblazer DJ Playero and other pioneers in the commonwealth rarely got such consideration.


Back then, of course, reggaeton didn’t even have a name. It wasn’t anywhere near the powerhouse genre it has become but rather an underground sound bubbling up inside Panama and Puerto Rico, as sonically and spiritually connected to American hip-hop as to Jamaican dancehall. To this day, the provenance of the genre’s eventual name remains in dispute, with some crediting Playero and Yankee while others cite DJ Nelson of seminal group The Noise for marketing the hybrid term.

No matter who rightfully deserves that particular distinction, Yankee has proved himself time and time again to make him not just a leader in música urbana but in hip-hop as a whole. Whether over a dancehall riddim, a dembow loop, or a boom bap beat, he truly is a G.O.A.T. emcee—full stop, no Spanish-language consideration or otherwise marginalizing categorization needed. Like Eminem or Lil Wayne or KRS-One or really whomever you cape for in hip-hop history, he’s made a few questionable creative moves, taken unexpected detours, and sometimes put out less than great material. But Yankee knows he’s a G.O.A.T., and doesn’t shy away from calling himself one. Now, with the latest generation of urbano talents like Anuel AA and Bad Bunny making hits worldwide, it’s time for everyone else to get with the damn program.

Thankfully, the streaming age makes it quite easy to get into Daddy Yankee, certainly more so than when he first broke out with “Gasolina” and the corresponding full-length Barrio Fino. Like so many mixtapes of the last couple decades, much of his early work remains in the legal aether, relegated to increasingly elusive hard copies and YouTube bootleg uploads. Still, enough of his expansive catalog exists legitimately on services like iTunes and Spotify to allow listeners to enter his discographic world from a variety of approaches.


So you want to get into: Rapero Yankee?

Anyone doubting Yankee’s rap bonafides off the rip might as well start with El Cangri.Com, considered his sophomore album following 1995’s Playero-produced No Mercy and a handful of compilations. With DJ Blass at the helm, the 2002 outing has a much more raw feel than the more polished fare the rapero makes today. While the bulk of the album relies on that unmistakable reggaeton rhythm, a handful of cuts look toward the genre’s New York City roots. One of its sample-based interludes pays homage to the concurrent post-millennium wave exemplified by Cam’ron and M.O.P., while “El Cangri” and “Sigo Algare” eschew the dembow for a beat closer to the digitized sound ringing through the five boros.

A rare English-language highlight off Barrio Fino, “Like You” finds Yankee again in that mode, spitting game while making overt nods to Big Pun and showing naysayers just how seamlessly reggaeton could integrate with New York hip-hop’s uptown vibes. A heightened profile post-”Gasolina” linked him with a number of then-contemporary American rappers, not the least of which being N.O.R.E., who would make a reggaeton album of his own. In addition to being a Yankee live album, 2005’s Barrio Fino En Directo also included a number of remixes and tracks with a continent spanning selection of artists such as Lloyd Banks, Snoop Dogg, and Paul Wall.

2007’s El Cartel: The Big Boss boasts one of the best Roc-A-Fella type beats of all time, the Humby-produced “Me Quedaría” as close to a Jay-Z swagger as Yankee ever ventured. Moving into the 2010s, he proved a reliable collaborator for savvy English-language and faithful Spanish-language rappers alike. As música urbana later welcomed the Latin trap wave, he adapted like an adept vet. Whether solo on 2018’s standalone “Hielo” or as a feature on any number of trapero duets and stacked posse cuts.


Playlist: “El Cangri” / “Sigo Algare” / "Like You” / “Machete (Remix)” / “Bring It On” / “Me Quedaría” / “Self Made” / “Hielo” / “Vuelve”

So you want to get into: Reggaetonero Yankee?

Distilling a discography as prolific as Yankee’s reggaeton catalog down to handful of essential songs is an exercise in futility. Instead, perhaps the best approach is to enter where so many of his fans did in 2004. “Gasolina” changed the game for reggaeton, and those who copped Barrio Fino caught him in fighting form. Infused with more distinctly tropical textures than other tracks on the album, the downright anthemic “Lo Que Pasó, Pasó" presented a palatable entry point in reggaeton for reluctant salseros and likeminded purists. Around the same time, Yankee joined an elite group of reggaetoneros including Tego Calderón and Ivy Queen on Eddie Dee’s single “12 Discípulos,” a landmark record.

Yankee kept that same energy in the immediately succeeding years, dropping aggro stormers like “Machucando” and “Rompe” off Barrio Fino En Directo. Those curious about what came before had the El interim compilation Los Homerun-es available to them. There, he teams with Don Omar on “Gata Gangster” and Nicky Jam on “Música Killa,” while going solo for the indispensable “Segurosqui.”

Reggaeton played a perennial part of all of Yankee’s subsequent albums, though later tracks like “Descontrol” and “” retain more of a sheen. A respectful throwback to the old school he helped elevate, 2018’s “Zum Zum” keeps it very fun and very real.


Playlist: “Segurosqui” / "Lo Que Pasó, Pasó" / “12 Discípulos” / “Machucando” / “Rompe” / “Miss Show” / “Descontrol” / “Zum Zum” / “Gasolina”

So you want to get into: Deejay Yankee?

In those formative years with DJ Playero, with the sound of reggaeton yet to take shape, Yankee’s contributions to projects like Playero 37 landed squarely in the dancehall category. Though it may be hard for “Despacito” listeners to wrap their head around the idea, he used to be quite the deejay (not a DJ), vocalizing on par with many of the Jamaican artists of the time. One listen to “Yo Nunca Me Quedo Atrás” shows just how beholden the young artist was to the genre. A number of his Playero features would reappear on Los Homerun-es.

The dembow riddim comes directly from dancehall, namely the Bobby Digital produced “Dem Bow” by Shabba Ranks, and Yankee played no small part in its popularization as the defining beat of reggaeton. Apart from that signature, reggae has endured over the years as part of the fabric of música urbana, its tropes and creative advances used widely by any number of reggaetoneros.

Years later, Yankee remains endeared to the form beyond dembow, as evidenced by his remix of Major Lazer’s “Watch Out For This (Bumaye)” with Busy Signal and his appearance on DJ Nelson’s dancehall version of the group single “Estás Aqui.” In 2018, he landed a Hot 100 charting hit with “Dura” and, more recently, he dropped a fresh interpolation of Snow’s “Informer” entitled “Con Calma”—and featuring none other than the white Toronto-born reggae singer himself.


Playlist: "Donde Mi No Vengas” / “Yo Nunca Me Quedo Atrás” / “Soy Pelon, Muerte Yo Le Doy” / “Shaky Shaky” / “Watch Out For This (Remix)” / “Dura “ / “Con Calma” / “Estás Aqui (Dance Hall Version)”

So you want to get into: Popstar Yankee?

Following 2008’s Talento De Barrio soundtrack and Yankee’s star turn in the movie, the reggaetonero seemed ready for bigger things. Obviously he’d played the crossover game before, and even the preceding El Cartel: The Big Boss contained a few mainstream-baiting overtures such as “Papi Lover” with Pussycat Doll Nicole Scherzinger and separate collaborations with two different members of the Black Eyed Peas. Yet the diverse styles present on Talento De Barrio showed his range without resorting to such stunt casting, flirting with glossy electro pop on “Pose” and “Pasión” as well as flirting with bachata and salsa elsewhere.

That wanderlust continued on 2010’s Mundial, where Yankee appropriated electro house, merengue, soca, and more, with mixed results. (The less said about the Daft Punk knock-off “Vida En La Noche,” the better.) Moving undeterred into 2012’s Prestige, he was unapologetic in his risk-taking reach beyond reggaeton for a more broadly commercial hit. Its dancefloor-centric single “Limbo” topped Billboard’s Hot Latin Songs, while the uptempo Natalia Jimenez duet “La Noche De Los 2” hinted at the lengths he’d go towards fulfilling his pop ambitions. That latter lean proved prescient, as anyone in the world who’s heard 2017’s ubiquitous “Despacito” with Luis Fonsi and Justin Bieber can attest.

Despite not releasing a proper album since 2013’s King Daddy, Yankee continues to grow his discography off of singles, features, and multi-artist collabs. He’s a modern mainstay of the vibrant Latin remix format, notably joining Camila Cabello’s smash “Havana” on on such mix. Lately, you can’t go more than a few weeks before he’s back with something new. In the last twelve months, he coaxed Janet Jackson back into the studio for “Made For Now,” tapped Latin trap star Anuel AA for “Adictiva,” and joined Akon and Sean Paul on Farruko’s “Inolvidable” remix, to name but a few.

With King Daddy’s planned follow-up El Disco Duro either completely dead in the water or overdue for a radical revision from what he originally intended with now former production partners Los De La Nazza, whenever Yankee opts to return to the album format, it will be the most anticipated album of the hitmaker’s decades-long career.

Playlist: “Papi Lover” / “Pose” / "Limbo” / “La Noche De Los 2” / “Daría” / “Havana (Remix)” / “Made For Now” / “Adictiva” / “Despacito (Remix)”