Presented by GRAMMY.com, Songbook is an editorial series and hub for music discovery that dives into a legendary artist's discography and art in whole — from songs to albums to music films and videos and beyond. In this edition, GRAMMY.com pays tribute to reggaeton legend Daddy Yankee, examining his biggest hits and most memorable collaborations.

Daddy Yankee goes by many names: The Big Boss. El Jefe. El Cangri. The King. While many of them are self-proclaimed, it’s undeniable that the artist is a reggaeton icon. In his nearly three-decade-long career, Yankee (real name Ramón Luis Ayala Rodríguez) has reigned tall with hardly any visible competition (with all due respect to Don Omar), and his journey to the top is the stuff of legends. 

In fact, the 46-year-old reggaetonero is the most successful person to emerge from the underground in the mid-'90s. He became el género's biggest export during its first international explosion in the aughts and, in the decades that followed, D.Y. has enjoyed a highly prolific career. As the genre currently enjoys massive mainstream popularity the world over, Daddy Yankee has also gained the respect and admiration of the majority of reggaeton’s new class.

Unbeknownst to many, Yankee coined the word "reggaeton" 1994 on DJ Playero’s seminal 1994 mixtape Playero 36 (DJ Nelson would popularize the word reggaeton the next year). His underground debut No Mercy (1995) laid the foundation for the future of reggaeton, fusing old-school hip-hop and turntablism against his signature dancehall-esque, quick-witted lilt. A decade later, Daddy Yankee fueled the reggaeton explosion with "Gasolina," and the rest is history.  

Six Latin GRAMMY wins and four GRAMMY nominations later, the Big Boss remains a global force to be reckoned with. Following D.Y.'s recent retirement announcement, GRAMMY.com pays homage to his prolific and highly influential body. From Barrio Fino to "Despacito" and Legendaddy, we examine the solo hits and collaborations that have made the Puerto Rican artist a living legend — and why countless of reggaeton newcomers are following in his footsteps. 

Listen to GRAMMY.com's official Daddy Yankee playlist on Spotify, Apple Music, Amazon Music, and Pandora.

The Global Hitmaker

The 2000s

Armed with a rapid-fire flow backed by a revving, EDM-driven thump, the former baseball player scored his first musical home run with "Gasolina" in 2004. Produced by Luny Tunes, the song became an instant gargantuan hit that unleashed reggaeton well beyond his island home.  

In the Americas, Yankee became known as the face of a burgeoning scene and the incendiary song became the gateway to the genre for those outside of the Caribbean diaspora. The album cover of Barrio Fino — a candid black-and-white shot of Daddy Yankee looking off camera, donning a New York Yankees cap — inspiring legions of followers to sport Yankees hats. 

In addition to expanding reggaeton’s international reach, the album is widely considered foundational for many reggaeton artists that followed. Daddy Yankee’s linguistic dexterity and influence on the genre was recognized at the 2005 Latin GRAMMYs, where "Gasolina" became the first reggaeton song to be nominated for the coveted Record of the Year; Barrio Fino earned him his first Latin GRAMMY for Best Urban Album Music. 

Nearly two decades later, Barrio Fino’s countless hits — like the party-starting "Lo Que Pasó, Pasó," about an old fling, and "Tu Prínicpe" — continue to ignite dance floors at block parties and bourgeois resorts alike. In 2005, Daddy Yankee followed up with a live album and four new songs, including "Rompe," a fire-in-the-belly banger for serious perreo enthusiasts. His  popularity accelerated well into the aughts, and Daddy Yankee was added to Time's list of 100 influential people in 2006.

The 2010s

The Boricua superstar journeyed to further sonic territory with 2010's Mundial, which employed  equal parts braggadocio and trap experimentalism as heard on "El Mejor de Todos Los Tiempos" and "El Más Duro." Early signs of the then-new Latin trap seeped through, thanks to producers Musicólogo & Menes, while the Yankee also embraced beloved Puerto Rican tropical rhythms (hear the merengue on "La Despedida" and "Rumba y Candela").

Prestige arrived a couple of years later with more memorable bangers at the intersection between EDM, reggaeton, and electropop. In 2012, the rapper told a news outlet in Miami that Prestige is his "best and most complete album" yet. The charts and viral streams confirmed it: flashy, swaggering numbers like "Limbo" and "Lovumba" both peaked at No. 1 on the Billboard’s U.S. Latin charts; and the former song currently boasts a staggering 1.2 billion views on YouTube.  

A new cohort of música urbana superstars that grew up on old school reggaeton — led by the likes of J Balvin, Ozuna, and, later, Sech and Karol G — gave the genre a more sophisticated makeover in the mid-2010s. Many of urbano’s rising stars cite Yankee as an inspiration, while their changes to the genre were also inspired by improved technology that refined production. 

Meanwhile, new reggaeton fans began to explore the roots of the genre. While genre O.G.s such as Don Omar experienced a back-catalog boost, many slowed their new music release momentum — not Daddy Yankee. To popular perception, this made the D.Y. the default genre originator, with hardly any visible competition from peers. 

During the later part of the decade, Daddy Yankee released a slew of singles and buzz-worthy collabs. As an unrivaled reggaeton icon, Yankee dropped "Shaky Shaky" and "Dura" to further virality. By the time of the reggaeton-pop of "Con Calma" (featuring Snow) and the tropical-soaked "Que Tire Pa Lante" — which samples vocals by the new hype generation including Bad Bunny, Natti Natasha, Anuel AA, and Darell, as well as genre pioneers like Wisin and Lennox — Daddy Yankee was unstoppable. 

The Powerhouse Collaborator

When "Despacito" arrived in 2017, the reggaeton movement spread like wildfire. Daddy Yankee’s artistry and decades of street cred paid off in a huge way when he joined former rock balladeer Luis Fonsi for the now-omnipresent smash hit. Beyond his existing fame, the track instantly transformed D.Y. into a full-fledged Latin pop phenomenon. The song itself took on a new life of its own: "Desapcito" currently clocks in at a staggering 7.92 billion views, making it the second most watched video in YouTube history. Today, reggaeton and Latin pop are used interchangeably, and popular Latin pop playlists are loaded with reggaeton songs.

Perhaps one of Daddy Yankee's most memorable collaborations is "Oye Mi Canto" by N.O.R.E., also featuring Nina Sky, Gem Star and Big Mato. Entering the Billboard Hot 100 at No. 12 in 2006, this song helped catapult reggaeton to mainstream success. "Oye" also put the Latino/a and Black Latino/a presence on the map at a time when MTV largely aired music videos by white and African American artists. 

Yankee's feature on "Machete" by Héctor El Father was another early banger that resonated throughout the underground. Released the same year that "Gasolina" dropped, the song channeled a similar bombastic energy and made maximalist reggaeton sound defiant.  

The New Class

Reggaeton’s new cohort further helped elevate Daddy Yankee’s star to newer heights. In 2020, Panamanian sensation Sech invited an all-star cast — including Farruko, J Balvin, Yankee and superstar Rosalía — to sing in the remix of his hit song "Relación." "Daddy Yankee is the Big Boss, the best of all time," said Sech. "He’s not about just arriving and making a hit, he’s about maintaining, and if we talk about maintaining, he has the record." 

As he continued to make huge strides within the ever-growing reggaeton empire, Daddy Yankee then stepped into Latin drill. In 2021, Yankee joined forces with Brooklyn drill pioneer Bobby Shmurda and J Balvin for a remix of trap rapper Eladio Carrión’s viral dissonant drill song "Tata." The song sees the D.Y. diving into darker territory while maintaining his bad boy image. 

At the same time, Yankee was shedding that image: A few years earlier, he joined Janet Jackon for a more gleeful pop duet in New York City, and helped break then-teen reggaeton upstart Lunay on the remix of "Soltera," joined by Bad Bunny. 

By combining sounds and styles from different generations, reggaeton is cementing its everlasting star power. This is exemplified in "Mayor Que Usted," a recent hit by Natti Natasha, Wisin & Yandel, and Daddy Yankee, which sees three artists of different stylistic leanings bring forward a potent reggaeton recipe. In the month and a half since its posting, the YouTube video already racked up 14.5 million streams. 

LEGENDADDY

When considering his biggest hits and collaborations, it’s undeniable that El Jefe has made epic strides. As he plans his exit in full galore, Yankee leaves us with a riveting record for the reggaeton-pop cannon that encapsulates his dynamic and linguistic prowess. There are plenty of moments in LEGENDADDY (his seventh and final studio album, released in March) where D.Y.'s creative brilliance shines through, but in contemporary Latin pop fashion, he invites plenty of others to share the spotlight, while making his claim as the G.O.A.T.

In "Agua" starring Rauw Alejandro and fabled guitarist Nile Rodgers, the three artists summon a revamped pop-funk for perreo under a disco ball. Bad Bunny’s hit-making streak continues on the exhilarating club track "X Última Vez," and El Alfa brings forward his frenetic Dominican dembow dazzle on "Bombón," alongside unlikely guest Lil Jon. Our main man re-returns to the native tropical rhythms of Puerto Rico on "Rumbatón," all in all accumulating to a welcoming, farewell homage that captures Daddy Yankee’s enduring legacy. 

From coining the genre to continually rewriting the música urbana playbook for over a quarter-century, and amassing 20.4 billion total YouTube views, there’s no denying that the Yankee has been helping transcend reggaeton’s cultural boundaries. As reggaeton enjoys plenty of global acclaim, this legendary daddy has every right to boast his bravado.  

Songbook: The Complete Guide To The Albums, Visuals & Performances That Made Beyoncé A Cultural Force

Música Mexicana isn't the only sound of Mexico that's blowing up; the country's artists are now starting to make their mark in reggaeton. Imbued with the essence, swagger, and lingo of Mexico, reggaeton Mexa is the next big Latin sound that's going global.

Originating in the Caribbean, reggaeton evolved from Panama’s reggae en español and Jamaican dancehall of the 1980s. Puerto Rican acts like DJ Playero and DJ Nelson shaped the sound of reggaeton in the island's underground scene during the '90s, while Daddy Yankee, Tego Calderón, Don Omar, and Ivy Queen pushed the genre into the mainstream at the dawn of the new millennium. 

Boricua acts Tainy, Bad Bunny, and Ozuna pushed reggaeton into the next decade, though Colombia also brought about the genre's second wind. J Balvin's success solidified Medellín as a reggaeton hotbed, spawning Maluma, Karol G, and Feid as global stars.

Learn more: The Sonic And Cultural Evolution Of Reggaeton In 10 Songs

In the 2020s, Mexico is becoming the next hub for reggaeton as artists who grew up listening to the Puerto Rican OGs  — as well as Mexican acts Ghetto Kids and Pablito Mix — are now putting their own stamp on the genre. In late 2022, Bellakath put a spotlight on reggaeton Mexa with her viral hit "Gatita"; the following year, Yng Lvcas took the sound to new heights with his "La Bebé" remix featuring Peso Pluma, which reached No. 11 on the Billboard Hot 100 chart. 

Reggaeton Mexa pulls from the genre's underground roots in Puerto Rico, infusing its songs with Mexican culture and grit. Lyrics are full of Mexican slang that reflect life in the barrios.

"Reggaeton Mexa is reminiscent of the sounds of the '90s and 2000s from Puerto Rican DJs like Playero and Joe," El Mallila, one of the reggaeton Mexa leaders, tells GRAMMY.com. "The songs, the beats, and rhythms are more or less similar to that flow. The difference here is the Mexican jargon. Reggaeton Mexa is spicy. We play with Mexican profanities without being offensive."

The emerging genre has gained traction among the larger reggaeton community with Jowell y Randy, Maldy, and J Balvin recently featuring on their songs. Following the success of Yng Lvcas, Bellakath, and El Malilla, Mexican acts like Peso Pluma (who dedicated part of his Éxodo album to reggaeton) and pop star Kenia Os are embracing the wave. As the tide continues to rise for reggaeton Mexa, GRAMMY.com is highlighting seven of the sound's leading artists.

Guadalajara, Jalisco native Yng Lvcas noted that no one around him could name a Mexican reggaeton artist, so he decided to fill that void.

An early encounter would make for auspicious beginnings. As he was signing a record contract with Warner early last year, Yng Lvcas crossed paths with Peso Pluma. The música Mexicana star's first foray in reggaeton was with Yng Lvcas and their global hit, a sensual remix of "La Bebé." Their collaboration became the first reggaeton song by Mexican artists to enter the Hot 100 chart.

Last October, Yng Lvcas released his album Super Estrellas to put a spotlight on more reggaeton Mexa acts. The LP included songs with El Malilla and El Bogueto. Puerto Rican OG Maldy later teamed up with Yng Lvcas for the hypnotic "Diviértete."

The first artist to get the global conversation started about reggaeton Mexa was Bellakath. After earning a law degree from the National Autonomous University of Mexico, the Mexico City native became a social media personality. Bellakath leveraged her following to start her music career, which exploded in late 2022 with the frisky "Gatita." The song went viral on TikTok and the music video has over 144 million views on YouTube.

In the male-dominated reggaeton Mexa scene, Bellakath is continuing to keep women on top. Last year, she released her debut album Kittyponeo with the hit "Reggaeton Champagne" featuring Dani Flow. After signing with Warner in May, Bellakath dropped "Sandunguea," which sampled the reggaeton classic "Mayor Que Yo" by Luny Tunes. On July 15, Bellakath released her second album, Sata 42, where she ventured into dembow music with artists from the Dominican Republic. 

Learn more: 5 Women Essential To Reggaeton: Ivy Queen, Natti Natasha, Karol G, Ms Nina & Mariah Angeliq

El Malilla proudly represents the chakalones (Mexican slang for "bad boys") in reggaeton Mexa. Hailing from Valle de Chalco, El Malilla remembers his first encounter with reggaeton as a teen came from the pirated CDs that were sold at the tianguis, or open-air markets.

Now, El Malilla is bringing Mexico's version of reggaeton to the forefront. He recently released his debut album ÑEROSTARS, which includes his viral hit "B de Bellako" with Yeyo. Back in May, Puerto Rican OGs Jowell y Randy jumped on a remix of the quirky banger. 

El Malilla also wants to make reggaeton Mexa more inclusive. Reggaeton has historically excluded LGBTQIA+ folks, though queer artists such as Young Miko, Villano Antillano, and La Cruz are changing that tune. On the Mexican front, El Malilla wanted to be an ally to his queer fans with the 2000-inspired "Rebote" music video, which was shot at the gay club Spartacus with Mexican drag queens. 

Within his album, El Malilla is also stretching the bounds of his artistry by exploring merengue in "Coronada" and experimenting with house music in "Todo Tiene Su Final." "ÑEROSTARS is a call to all the reggaeton Mexa artists to dare themselves to make new music and try different sounds," he says. "Don’t stay in your comfort zone just making perreo."

Veracruz native Yeri Mua is keeping a high heel firmly planted on the neck of the genre, holding it down for the women in reggaeton Mexa.

Mua started out doing makeup tutorials on YouTube and later grew a massive social media following. Last year, she launched her music career on Uzielito Mix's reggaeton romp "Línea del Perreo," which has over 103 million streams on Spotify. In songs like "Chupon," Mua brings a fierce femininity to reggaeton Mexa while flipping the genre's explicit lyrics from a woman's perspective. In April, Kenia Os tapped Mua and Ghetto Kids for her reggaeton Mexa banger "Mamita Rica." With a laugh, Os told GRAMMY.com at the time, "[Mua] sounds very sexy and makes noises like meowing. It felt very great to work with her." Last month, Mua signed a record contract with Sony Music México.

Alongside El Malilla, El Bogueto is one of the OGs of reggaeton Mexa. The Nezahualcóyotl native has scored a number of hits since 2021, including "Tu Favo" and "G Low Kitty," which has nearly 60 million streams on Spotify.

The title of El Bogueto's 2023 debut album Reggaetoñerito is an amalgamation of the words reggaetonero and ñero, which is Mexican slang for a person from the hood. El Bogueto has continued to rack up millions of streams with his LP, which include hits like the freaky reggaeton romp "Piripituchy" and "Dale Bogueto." In May, J Balvin gave his co-sign to El Bogueto and the reggaeton Mexa scene when he jumped on an all-star remix of "G Low Kitty."

Among the artists on this list, Yeyo is the freshest one on the reggaeton Mexa scene, but he's fast becoming one of the genre's brightest stars and the go-to artist for a hit collaboration. The Zacatepec, Morelos native is a protege of Ghetto Kids' Luis Díaz, who also serves as his manager.

Yeyo's playful and infectious flow as a Mexican reggaetonero has translated into million of streams in songs like "B de Bellako" with El Malilla and "Mami Chakalosa" alongside Bellakath. He has also flexed a romantic side to his distinct voice in Ghetto Kids' recent hit "En El Ghetto #5 (La Discoteca)." Yeyo has also shined on the electronica-leaning reggaeton of "Maldad" and the sensual "Tentación."

Many of the songs mentioned in this list wouldn't have been possible without Uzielito Mix. Following in the footsteps of Ghetto Kids and Pablito Mix, the Mexico City-based producer has become the backbone of the sound of reggaeton Mexa. Uzielito Mix produced Yeri Mua's hits like "Línea del Perreo" and "Brattiputy." He also co-produced El Bogueto and El Mallila's "G Low Kitty" with DJ Rockwell, which J Balvin later hopped on. 

In his stellar collaborations, Uzielito Mix is known for uniting many of the reggaeton Mexa stars. He continues to push the sound of the genre into the future like in the spooky "Espantan" remix with El Bogueto, Alnz G, Dani Flow, and Tensec. In 2022, Bad Bunny tapped Uzielito Mix to open his World's Hottest Tour stops in Mexico City. 

Álvaro Díaz has a twinkle in his eye — he knows he’s onto something special.

"It’s crazy that it’s an alternative album, but also the most reggaeton I’ve ever made," Díaz says of his recently-released sophomore album, Sayonara. "It’s both worlds. I have my fingers crossed that people are going to love it."

Díaz, who is 28, has been making music since he was a teenager. A constant creative force, he grinded for years as an independent artist, building a solid fanbase in Puerto Rico before breaking into the wider Latin urbano scene with 2021 debut, Felicilandia, which layered fresh pop melodies onto playful reggaeton and trap beats, exploring the euphoria of love.

Notably darker and much more experimental than its predecessor, Sayonara marks the end of that "happyland" feeling. 

"My story with ‘Felicilandia’ ended in heartbreak," he tells GRAMMY.com. "I was just writing about my life. It’s like a nightmare when you can’t stop thinking of that person. The usual Puerto Rican [reaction] to a breakup is like,'Don’t worry, let’s go to the streets!'"

The first half of the record soundtracks this feeling of party and abandon. Perreo tracks like the Feid-featuring dancefloor banger "Gatas Sandungueras Vol.1" nod to old school reggaeton, while Diaz and guest Tainy twist into ravey house beats on "Fatal Fantassy."

With an assist from Spanish indie pop star Sen Senra, "1000Canciones" marks a turning point in the album’s mood. It’s slow, reflective and poignant, with unashamedly heartfelt lyrics. "I went to the streets, and played 1000 songs that reminded me of you / even though I knew it was late / I took my phone to call you," Diaz sings in Spanish.

Lovingly nicknamed "Sadvarito"by fans, Diáz’s vulnerability stands out amidst a reggaeton scene dominated by party hits and swag. Even the biggest hits on Felicilandia— "Lori Party" and "Babysita </3" — were tinged with heartbreak; and fans will be reassured to see his signature fragility thoroughly embedded in Sayonara.

"It’s just how I feel, sometimes I feel empty, sometimes there’s a lot to say," Díaz says of the album’s changing moods. 

At the end of the album, Díaz considers trying to get back with his former flame ("Quizás si, quizás no," featuring Quevedo). But, he soon realizes it won’t work: "You know it’s not the same — it’s just me saying 'Sayonara,'" he says. 

GRAMMY.com spoke with Díaz over Zoom about why reggaeton is the perfect heartbreak genre and how ‘Sayonara’ is his most experimental work yet.  

This interview has been edited for clarity and length.

Sayonara **comes three years after your debut, Felicilandia. There are some similarities in the two albums’ artwork, but we can see something’s gone a bit awry/**

There’s an explosion at the left of the Felicilandia artwork. We were predicting what was going to come. I’m a fan of when artists do these little things, merge album covers, or make songs that live in the same universe. 

Felicilandia is the way to find happiness, Sayonara is saying goodbye to the happiness you thought you found. 

When you’re with a person you create a world together. But, todo se fue a la mierda. That world has gone. On [the artwork for] Sayonara, I’m looking ahead, but you don’t know my intention. I could try to save everything, or I’m just taking the last look. 

The track ‘‘Gatitas Sandungueras Vol. 1’ feat. Feid, has dark undertones, even though it’s a song about partying.  How is the track related to the album’s main theme of overcoming heartbreak?

Me and Feid put everything into the song. It’s based on the story of missing her: you’re blind; you’re trying not to think about her.  

Feid is like my duo, we always talk about making projects together, and our fanbase likes it when we work together. He couldn’t be out of ‘=Sayonara —he was in Felicilandia singing a sad song, and now he’s singing a party song, so it’s a total contrast. 

Same with Rauw Alejandro, who is on the track "BYAK," and was also on Felicilandia single "Problemón."  It’s special to have Feid and Rauw on both albums. We didn’t want to repeat what we did before, we wanted to go in another direction. 

The album mixes a lot of different genres, but reggaeton is definitely at the foundation of Sayonara. What artists were your core inspirations?

The selection of the sounds, and the beats, reminds me of the golden era of reggaeton in the 2000s. We even used the old Fruity Loops software, and searched for inspiration in [LunyTunes & Tainy 2006 album] Mas Flow: Los Benjamins, or the [2003 compilation album], Blin Blin. All those albums that changed your life in Puerto Rico. That’s why the reggaeton tracks have 2000 vibes, it’s what I listen to. 

You’re known for making an emotional brand of reggaeton. When did you first explore reggaeton’s potential to be more vulnerable?

My fans’ favorite songs are my most heartfelt songs. Maybe my most played song on Felicilandia is "Problemón," but on tour, the song people go crazy for is "Babysita." It’s a song I recorded in my house, but it’s bigger than all my other tracks. 

So, I know how the people who follow me connect with me. The way I talk about heartbreak speaks to a lot of people; it’s more relatable than how other people sing about it. They call me "Sadvarito," so it was always a challenge to find a way to bring that Sadvarito energy to reggaeton. 

What is your favorite reggaeton heartbreak song?

Damn, there’s a lot. It’s hard. 

My favorite reggaetoneros growing up were Zion & Lennox, they were my GOATS, and most of their songs are heartbreak songs. So, Zion & Lennox, "Solo Una Noche." 

There’s also a song on [Luny Tunes-produced 2005 compilation album] Mas Flow 2 which is my favorite ever: "Es Mejor Olvidarlo." That’s my jam. I used to blast that when I was little. I didn’t know heartbreak then, but I felt that.  

So you can cry to reggaeton?

You definitely can! Old school people may say you can’t, but, ey, reggaeton be having feeling. It will make you feel a type of way in a club. It could change your mood completely.

Connecting with fans is everything to you. On Sayonara, how are you hoping to reach people?

I have a really hard time saying goodbye. There’s a phrase: la esperanza es lo último que se pierde, I’m one of those types of guys; the last one who loses hope even if my world is going to pieces. I want to make her fall in love, like on the track "Quien te quiere como el nene." It’s saying I really love you, I want to fix things. 

The point of the album is for people to see what chapter they’re in. I’ve never been able to reach the last track, to finally be able to say Sayonara, but I know I will get there! 

One woman who listened to the album said it’s awesome to hear a man’s perspective — you go out and party, and then you miss her. She said, usually, for girls, it’s the other way around: you miss him at the beginning, then you go out to party. It gives it realism, boys really be like that. I love it when real life and music come together. I really hope people find themselves in the songs.

"Quien te quiere como el nene" is one of the more experimental tracks on the album, and unexpectedly goes into a drum and bass rhythm. How did that come about?

I did that whole beat with my mouth! I had it in my mind. I had the bass, but it needed a sound there. I don’t know why but I started making these sounds. I sent a demo to Tainy and asked, "Do you think you can do this?" Obviously, he can, he’s Tainy. Alongside Manuel Lara, my main producer, they took it to the next level. They are a dream team. 

You break from the reggaeton beat a lot in the album — "Fatal Fantassy" is very house. Tell us about these electro elements.

I like to experiment with different sounds. It’s harder for me to do reggaeton than do experimental things. Different tracks just come naturally. Tainy and I were listening to the album after we had 60 percent of it ready, and we felt like it was missing energy, it needed a bit more uptempo. So we did three sessions and came up with those ideas. 

I made a playlist with everything I want to do in the album, so I could say "I want a riff like this." I like to take a lot of ideas and work them little by little. My process is different to a lot of my friends who go to the studio and make three or four songs a day. I really like to feel like what I’m creating.  

You’re in Japan right now, and this album frequently mentions Japanese words, people and culture: from "Sayonara," "Kawa," "Majin Buu" and "Yoko." How did Japan influence you?

Japan is really important in this album, the names, the creation. I didn’t want it to be obvious, but it’s there, in the minimalism, the names, It’s magical for me to be now in Japan and listen to the album. I can say, damn this song feels like Toyko, this one feels like Osaka. Now I’m in Kyoto, and I feel "Quien te quiere como el nene" is definitely a song for this city. 

I’m a cinematographic guy, I create songs with movies on mute. I recreate the vibe, how I feel it would sound. Even movies filmed in Japan, like ‘Lost in Translation’—I watched that a lot and was inspired by that. That feeling of being lost, of not knowing what’s next. 

"Majin Buu" is one of the most heartfelt tracks on this album, and references a "Dragon Ball Z" villain. Why do you draw on that character?

It’s a 2024 alternative love poem! He’s a bad guy, but I flip and use it in a good way. 

I like to play with names, most of the time I have the name of the song. I knew I wanted to make a song with Majin Buu but I didn’t know how it was going to sound. The same day I made "Majin Buu," I made the track "Yoko."

Speaking of "Yoko," do you relate to the person who has been painted as the bad guy?

Definitely. When I watched the Get Back documentary about the Beatles on Disney+, I remember seeing Yoko every single moment beside John Lennon. They were inseparable until his last day. All the Beatles had a family, they all had wives, but it was Yoko who was next to John at every moment. 

It was a romantic way to say, I want you by my side like Yoko was with John Lennon. 

You're very close to your fanbase. Is there anything that artists can do to stay grounded with their fans? As you’re getting bigger, how do you manage the relationship with fans?

Fans made me. Especially during those years when my project didn’t have the light it deserved, my fans were there for me. It’s important for me to have a healthy relationship with them. 

I always try to put myself in the shoes of a 16-year-old and think what things could he say to me to make me fall in love with this project?, or what did this artist do that made me a superfan? I try to create experiences. In the run-up to releasing Sayonara, we did listening parties with 15 fans in different parts of the world, with exclusive merch. Seeing the reactions of the people is important for me. 

I’ve been making music since 2012. Some [artists] don’t know the hustle; they get big after two to three years. But [success] is not given, it’s earned. I get the rockstar mentality, but that’s not me. It’s impossible for me to lose touch with the fans. 

[Sayonara] is a celebration for me and for the fans. I want to do small shows in Puerto Rico, places I played when I was started. I love the shows where you can feel people’s emotions. When you get big, you kind of lose that. But to me, that connection is magical, I never want to lose that.

Kenia Os Unveils Her 'Pink Aura': How The Mexican Pop Star Let Her Feminine Energy Shine

Once a marginalized genre associated with lewdness and criminality — much like the genres from which it draws so much influence, dancehall and hip-hop —  reggaeton is now firmly in the mainstream. While dominant across Latin America in the new millennium, reggaeton has made huge inroads with English-speaking audiences in the past decade, particularly with crossover hits like "Bailando," "Despacito," and numerous Bad Bunny songs from the past three years.

Although many associate reggaeton with Puerto Rico, the roots of the genre can be found in Panama, with artists like El General and Nando Boom taking Jamaican dancehall riddims — like dembow, first introduced in the Shabba Ranks song of the same name — and rapping in Spanish over them in the early 1990s. In Puerto Rico, early reggaeton was called "underground," and gained popularity in the mid-1990s through mixtapes put out by DJs like Playero and Negro, who utilized hip-hop techniques to alter the dancehall riddims as an instrumental track for local rappers and singers like Daddy Yankee.

Reggaeton has long been a male-dominated genre (with Ivy Queen being the main exception to the rule), but in recent years female singers have become more prominent. Colombian singer Karol G, for example, is currently one of the genre’s biggest stars, and Spanish singer Rosalía pivoted to reggaeton for her 2022 album Motomami, which won a Latin GRAMMY for Album Of The Year. 

Colombian artists have also been making their way to the top of the reggaeton charts in recent years — alongside Karol G, there’s J Balvin and Maluma — although Puerto Rican artists still dominate the genre, with current stars like Rauw Alejandro and Anuel AA.

Reggaeton will only continue to evolve and develop; read on for 10 songs that represent the sonic and cultural evolution of the genre in the past three decades.

El General - "Tu Pum Pum" (1990)

Years before the term reggaeton was invented, Panamanian rapper El General (Edgardo Franco) was the first artist to gain recognition recording reggae en español. Given the history of West Indian immigration to Panama to build the Canal, it’s not surprising that the story of reggaeton begins there. This proto-reggaeton style emulated Jamaican dancehall much more closely than later styles would. El General and his friends got started by taking Jamaican riddims like the genre-defining dembow and rapping in Spanish over them; they used to board buses in Panama City and perform for fellow riders. El General was known as a skilled improvisor.

He moved to New York to study in the late 1980s, and hooked up with fellow Panamanian and producer Michael Ellis, who is said to have invented the term "reggaeton." El General’s first hit, "Tu Pun Pun" is a Spanish-language version of Jamaican dancehall artist Little Lenny’s 1990 song "Punnany Tegereg" that’s quite faithful musically to the original. 

The title of the song is slang for female genitals, and the lyrics chronicle El General’s sexual prowess in graphic detail. Its chorus chants, "Your pum pum, baby baby, won’t kill (tame) me." The song became a hit in the U.S. and El General went on to have a successful, albeit brief, career. 

Tego Calderón - "Pa’ Que Retozen" (2003)

One of the biggest tracks on Tego Calderón’s debut album, El Abayarde, "Pa’ Que Retozen" was a party anthem and one of the first reggaeton hits in the U.S. It represents the culmination of many musical shifts that took place during the 1990s in Puerto Rico. By the mid-1990s, the dembow riddim began to dominate the Puerto Rican underground scene. As the millennium approached, DJs and producers began to incorporate elements of Latin popular music genres as well.

"Pa’ Que Retozen" is a good example of this trend, as bachata-style guitar riffs play underneath Calderón’s rapping. The background track switches up several times in this song, including an incredibly catchy, high-pitched synth riff heard in the second verse. Other tracks on El Abayarde also incorporate Latin genres and instruments — like bongó drums on "Abayarde," Afro-Puerto Rican bomba percussion on "Loíza," and a full salsa orchestra and vocals on "Planté Bandera."

Ivy Queen - "Quiero Bailar" (2002)

Known as the "Queen of Reggaeton," Ivy Queen was the only prominent female reggaeton artist for nearly two decades. She released two albums in the late 1990s, but it was her third album, Diva, in 2003, that really broke through. Ivy Queen intentionally wrote from a female perspective, as she had come up in a male-dominated scene in San Juan where women were constantly being objectified.

With her deep, throaty vocal tone, Ivy Queen proclaims on "Quiero Bailar" that although she wants to dance — even in the sexualized perreo style that had become synonymous with reggaeton — that doesn’t necessarily mean she wants to have sex with her dance partner. The song is still an important anthem for women who want to feel free to bump and grind and express themselves on the dancefloor without men expecting a sexual encounter. 

Don Omar - "Dile" (2003)

Three of the genre’s most influential artists exploded on the scene at roughly the same time: Calderón, Daddy Yankee and Don Omar, with the latter two involved in a rivalry for the title of "King of Reggaeton." However, Don Omar always stood out among the three for the lyricism of his voice — he was a more gifted singer than many of his peers.

His debut album, The Last Don, is considered to be a classic, utilizing a similar approach as Calderón of injecting more melodic Latin styles, like bachata and salsa, into his music. The Dominican production team Luny Tunes, who was instrumental in expanding the sound of reggaeton and distinguishing it further from its Jamaican roots,  produced about half the album’s tracks.

Like "Pa’ Que Retozen," Don Omar’s first major single, "Dile" relies heavily on a bachata guitar line, but his vocal style is quite different from the deep, resonant rapping of Calderón. The combination of Don Omar’s tenor voice with the melodic instrumentals of "Dile" makes for a very aesthetically pleasing, yet danceable song. In addition, he interpolates a salsa song, Joe Arroyo’s "La Noche," into a bridge-like section in the middle of "Dile." 

The subject matter is also more emotional than many reggaeton songs had been up to this point, as he’s pleading with a woman to tell her boyfriend that she wants to be with someone else (Don Omar).  

 Daddy Yankee - "Gasolina" (2004)

The first reggaeton song to be nominated for Record Of The Year at the Latin GRAMMYs, "Gasolina" still stands as the genre’s most iconic and recognizable song. The song catapulted not only Daddy Yankee into the mainstream, but also the genre itself. It appeared on Daddy Yankee’s third studio album, Barrio Fino, which broke numerous records and won many awards.

Barrio Fino took a broad approach, which proved incredibly successful. Many of the album’s tracks were produced by Luny Tunes, including its two biggest hits, "Gasolina" and "Lo Que Pasó, Pasó." The album also features a salsa-reggaeton fusion and an R&B-inflected rap song that sounds like it could have been recorded by Big Pun.

As for the concept behind "Gasolina," Daddy Yankee was living in a San Juan housing project with his family, where he often heard people on the street shouting, "iComo le gusta las gasolina!" ("How she likes gasoline!"), referring to women who accept rides from men with nice cars. He took that phrase and ran with it, creating the famous hook "A mí me gusta la gasolina, dame más gasolina" ("I like gasoline, give me more gasoline"). A decade later he laughed at the idea that the term "gasolina" referred to drugs — as many people assumed — claiming that he used it literally, to refer to cars. 

"Oye Mi Canto" - N.O.R.E., feat. Nina Sky, Gem Star, Daddy Yankee, and Big Mato

Reggaeton exploded in popularity in the mid-aughts, which explains why there are so many classic songs from that time period. "Oye Mi Canto" was the first collaboration between an American rapper (N.O.R.E.) and reggaeton artists, and included verses in English and Spanish.

The song originally featured Tego Calderón but Daddy Yankee replaced him in the video. It also signaled an acceptance of reggaeton by New York hip hop artists — Fat Joe also appears in the video. It peaked at No. 12 on the Billboard Top 100, a first for a reggaeton song.

The song utilizes a common feature of commercial hip hop at the time, a catchy R&B hook sung by a female vocalist, Nina Sky. The hook borrows from and adapts the recognizable chorus "Boricua, morena, Boricua, morena," which was heard on Big Pun’s massive 1998 hit "Still Not A Player," but extends it to include other Latino ethnicities beyond "Boricua" (Puerto Rican).

Calle 13 -"Atrévete-te-te" (2005)

Hardly a traditional reggaeton group, Calle 13 nonetheless created one of the genre’s most popular, beloved songs in 2005 with their irreverent hit "Atrévete-te-te." Rapper Residente and instrumentalist/producer Visitante, step-brothers, founded the group in 2004, and gained fame with a song about the FBI killing of Puerto Rican independence leader Filiberto Ojeda Ríos called "Querido FBI."

Residente is the most politically outspoken rapper within reggaeton, a genre the two musicians have tended to distance themselves from, preferring not to be labeled. The group’s music has always been eclectic, using live instrumentation and unusual timbres. These elements undoubtedly relate to the fact that Visitante plays dozens of instruments. The brothers still hold the record for most Latin GRAMMY Awards in history, a whopping 27 each!

"Atrévete-te-te" is an infectious cumbia-reggaeton hybrid featuring an unforgettable high-register clarinet. Residente’s lyrics are raunchy, witty, and replete with American pop culture references and anglicisms. He dares a "Miss Intellectual" to get down off her culturally elitist high horse and let loose: "I know you like Latin pop rock, but reggaeton gets into your intestines, under your skirt like a submarine, and brings out your ‘Taino’ (indigenous people native to Puerto Rico)." He reinforces his point later, singing, "Who cares if you like Green Day? Who cares if you like Coldplay?"

"Bailando" - Enrique Iglesias feat.Descemer Bueno and Gente de Zona (2014)

In the 2010s reggaeton’s popularity continued to grow, and "Bailando" was one of the songs that significantly raised the genre’s visibility among English-language audiences. Nonetheless, Spanish pop singer Enrique Iglesias originally didn’t like the song.

"Bailando" was written and recorded by Cuban singer/songwriter Descemer Bueno and Cuban reggaeton duo Gente de Zona, who had become one of the island’s biggest musical groups. When Iglesias heard Bueno’s recording, he changed his mind and they added his vocals. 

Garnering many awards, and winning Song of the Year at the 2014 Latin GRAMMYs, "Bailando" was flamenco-infused reggaeton designed for mass appeal. It follows a traditional pop song format, with Iglesias singing the verses and trading off with Gente de Zona and Bueno in the extended chorus sections. The lyrics are standard love song fare, and don’t include any of the rapped vocals or Cuban slang that had made Gente de Zona so popular in Cuba. Nonetheless, it peaked at No. 2 on the Billboard Hot 100 and spent a record-breaking 41 weeks at the top of the U.S. Latin charts. 

"Despacito" - Luis Fonsi featuring Daddy Yankee, with a remix feat. Justin Bieber (2017)

Love it or hate it, it’s impossible to ignore the cultural impact of "Despacito." It was already a huge hit in its original version, by Puerto Rican singer Luis Fonsi and Daddy Yankee. But when Justin Bieber called Fonsi up to inquire about doing a remix, it became 2017’s song of the summer.

Like "Bailando," the original version was already as much Latin pop as it was reggaeton, and although Daddy Yankee has some rapped vocals in the second verse, he’s mainly singing as well. The producers decided to use a Puerto Rican cuatro, which opens the song, in addition to an acoustic guitar in order to give the song a more local feel. One unique element was the insertion of a rhythmic break right before the chorus "Despacito" (which translates to "slowly") comes in. The way Fonsi breaks up the three syllables in the title word, taking his time with them, is a nice touch.

The Justin Bieber remix was released three months later, and maintained the song’s original rhythms and Daddy Yankee’s verses. An English verse was added for Bieber at the beginning of the song, and he sang the "Despacito" choruses in Spanish — the first time he’d ever sung in Spanish. It quickly rose to No. 1 on the Hot 100 charts, which gave Fonsi and Daddy Yankee their first No. 1 hit. It stayed at the top of the charts for 16 weeks, tying with "One Sweet Day," by Mariah Carey and Boyz II Men, and remained the longest-leading No. 1 single until 2019. "Despacito" also won Song and Record Of The Year at the Latin GRAMMYs.  

"Titi Me Preguntó" - Bad Bunny (2022)

Bad Bunny is not only the most prominent artist in contemporary reggaeton — he was the biggest artist in the world in 2022. It’s impossible to list all of the accolades Benito Antonio Martínez Ocasio has attained in his short career, but here are a few: His latest, Un Verano Sin Tí, was the first Spanish-language one to be nominated for Album Of The Year at the 2023 GRAMMYs, he's been Spotify's most streamed artist in the world for three straight years.

Un Verano Sin Tí was a masterful achievement, showcasing a wide variety of contemporary Latin music beyond reggaeton, including Dominican dembow and mambo, bachata, electro-cumbia, and even indie rock — all anchored by Bad Bunny’s emo vocal style. The album is a celebration of Spanish Caribbean identity, paying homage as much to Dominican as to Puerto Rican music.

"Titi Me Preguntó" is not only one of the album’s biggest hits, but also one of its most complex tracks, featuring several discrete sections. It begins with a bachata guitar intro, followed by Bad Bunny’s rapped vocals accompanied by a sparse backbeat. His aunt is asking why he goes out with so many girls and won’t settle down. The body of the song speeds way up, keeping a sparse accompaniment, as Bad Bunny lists the names and cities of different girlfriends. 

But there’s an interesting shift at the 2:15 mark, where the bachata guitar returns and we hear a woman’s voice admonishing him for being an f-boi. It’s followed by anguished Bad Bunny vocals singing, "I’d like to fall in love but I can’t." The music changes back to the sparse backbeat accompaniment when he sings: "I don’t even trust myself," and notes how many women say they want to have his first-born child. The singing returns, as a spooky electronica melody is added into the background mix: "Listen to your friend, I’ll only break your heart…I don’t know why I’m like this." 

This is a man struggling with interpersonal demons, and this vulnerable masculinity (and his past refusal to conform to rigid gender norms) is precisely why Bad Bunny is so beloved by his female fans.  

The Evolution Of Bollywood Music In 10 Songs: From "Awaara Hoon" To "Naatu Naatu"

Updated Friday Oct. 13, 2023 to include info about Kendrick Lamar's most recent GRAMMY wins, as of the 2023 GRAMMYs.

A GRAMMY veteran these days, Kendrick Lamar has won 17 GRAMMYs and has received 47 GRAMMY nominations overall. A sizable chunk of his trophies came from the 58th annual GRAMMY Awards in 2016, when he walked away with five — including his first-ever win in the Best Rap Album category.

This installment of GRAMMY Rewind turns back the clock to 2016, revisiting Lamar's acceptance speech upon winning Best Rap Album for To Pimp A Butterfly. Though Lamar was alone on stage, he made it clear that he wouldn't be at the top of his game without the help of a broad support system. 

"First off, all glory to God, that's for sure," he said, kicking off a speech that went on to thank his parents, who he described as his "those who gave me the responsibility of knowing, of accepting the good with the bad."

Looking for more GRAMMYs news? The 2024 GRAMMY nominations are here!

He also extended his love and gratitude to his fiancée, Whitney Alford, and shouted out his Top Dawg Entertainment labelmates. Lamar specifically praised Top Dawg's CEO, Anthony Tiffith, for finding and developing raw talent that might not otherwise get the chance to pursue their musical dreams.

"We'd never forget that: Taking these kids out of the projects, out of Compton, and putting them right here on this stage, to be the best that they can be," Lamar — a Compton native himself — continued, leading into an impassioned conclusion spotlighting some of the cornerstone rap albums that came before To Pimp a Butterfly.

"Hip-hop. Ice Cube. This is for hip-hop," he said. "This is for Snoop Dogg, Doggystyle. This is for Illmatic, this is for Nas. We will live forever. Believe that."

To Pimp a Butterfly singles "Alright" and "These Walls" earned Lamar three more GRAMMYs that night, the former winning Best Rap Performance and Best Rap Song and the latter taking Best Rap/Sung Collaboration (the song features Bilal, Anna Wise and Thundercat). He also won Best Music Video for the remix of Taylor Swift's "Bad Blood." 

Lamar has since won Best Rap Album two more times, taking home the golden gramophone in 2018 for his blockbuster LP DAMN., and in 2023 for his bold fifth album, Mr. Morale & the Big Steppers.

Watch Lamar's full acceptance speech above, and check back at GRAMMY.com every Friday for more GRAMMY Rewind episodes. 

10 Essential Facts To Know About GRAMMY-Winning Rapper J. Cole