Jam has a history of finding success where you'd least expect it. Born Nick Caminero, he started rapping at local talent shows in his native Lawrence, Mass., hardly a Latin music hotspot. After his father moved the family to Puerto Rico to "go back to our roots" when he was 10, Jam was discovered at a grocery store, where he would entertain himself by freestyling about the foods he was bagging. An impressed customer brought him to a local indie label, through which Jam released his rap/reggae debut, ...Distinto a los Demas, in 1994 at 14 years old. His bilingual flows caught the attention of DJs and vocalists whose mixtapes were forming the basis of a harder-edged sound that combined reggae rhythms with rapped vocals and Latin instrumentation: reggaeton. "I used to open for these big singers -- they were 20, 25 years old, and I was a kid with a Mickey Mouse voice, trying to speak Jamaican," recalls Jam. "I was like the little brother."
His favorite was then-rising star Daddy Yankee. The underage Jam would usually be escorted out of clubs after his own shows, but one night he managed to stick around long enough to introduce himself to his hero. The admiration was mutual, and Yankee asked him to become his hypeman. The pair became inseparable and collaborated on a handful of hits in the genre's turn-of-the-millennium golden era ("En la Cama," "Guayando"). But the growing success was overwhelming, and Jam began abusing drugs and alcohol. "I was making too much money. I was too young," he says. "I didn't know how to deal."
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Yankee began criticizing his bad habits, even subtly checking him on a record. "Yankee felt like he was like my father. I took it too seriously and made a whole song for him," explains Jam, referring to a 2004 tiraera (slang for diss track) over Fat Joe's "Lean Back" instrumental. "That wasn't a good choice, because he came with [2004 Billboard Hot 100 smash] 'Gasolina.' [I] looked stupid. He went his way, I went my way -- and obviously my way didn't go very well."
Yankee became reggaeton's biggest star after "Gasolina," while Jam was suddenly a pariah in the very music he helped popularize. Depressed, he gained weight, quit recording and supported himself and his habits with that hotel gig, singing lounge music for tourists he hoped wouldn't recognize him. It was his lowest point, but it also planted the seeds for his comeback. The shows forced him to develop his singing voice, which inspired him to head back to the studio. "I was a rapper. I didn't know I could sing. I saw a bunch of artists [succeeding] that didn't have that. I was like, 'I'm over here doing nothing -- I should be there.' "
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But he knew he couldn't do it at home. In 2007, he moved to Medellin, Colombia, where he found venues that would still book him and a reggaeton scene that welcomed him. "They made me feel like I was a legend. The boost they gave me made me want to be a better person. I started eating OK, I stopped drugs, I stopped alcohol. People came to love me because I was loving myself."
Scoring a few regional indie hits, Jam re-emerged as part of a new wave of Medellin reggaetoneros including J. Balvin and Maluma. In 2014 "Voy a Beber" broke through globally, reaching No. 29 on the Latin Digital Songs chart. Follow-up "Travesuras" went to No. 4 on Hot Latin Songs, helped land Jam a recording deal with Sony U.S. Latin earlier this year, and caught the ear of Latin's crossover king. "He called me when I was here in Madrid last year: 'Hey, I'm Enrique Iglesias,' " recalls Jam with a laugh. "I didn't believe him. I hung up! He called back, I heard his Spanish accent and finally believed him."
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"I've been a fan of Nicky's for a while, but what was really interesting is how moving from PR to Colombia shook his musical style," Iglesias tells Billboard. "He's writing songs I love."
Released in February, their collaboration, "El Perdón," an achingly romantic plea heavy on melody and reggae flourishes -- all touchstones of Medellin reggaeton -- went on to spend a whopping 30 weeks atop the Hot Latin Songs chart (it's currently No. 2), a run second only to Iglesias' 2014 smash "Bailando." In May, the song's success helped Jam secure a deal with Creative Artists Agency for representation. He spent the first part of fall performing "El Perdón" on tour with none other than Daddy Yankee, with whom he reconciled after a random run-in. "We saw each other on a plane, in first class," says Jam. "I told him I was sorry, he told me he was sorry. He didn't need to. We're friends."
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Now Jam has his sights set on even bigger successes. An English version of "El Perdon," retitled "Forgiveness," reached No. 56 on the Hot 100. Jam is writing for Iglesias' next album and finishing his own, due in early 2016. On Nov. 19 he's up for three awards at the Latin Grammys in Las Vegas. Jam is excited but most of all grateful. "What happened in my life made me a better artist," he says. "I know this because every time I do a song, I feel that passion. When I'm in that studio, I feel like I'm the king of the world. If I lose that, I'm going to lose a lot."
Listen to Nicky Jam and other artists featured in this week's issue of Billboard.