They quickly rose to fame with the recording of the 2000 album Los Reyes del Nuevo Milenio. They later made the jump to a major label in 2003 with Mi Vida… My Life. De Nuevos a Viejos (2001), Mi Vida… My Life (2003) and De Otra Manera (2004), all of which were certified gold. The duo went on to receive the Tu Música Award for Best Rap/Reggaeton Duo in 2002.

In 2013, after their Líderes tour, Winsin and Yandel each went their separate ways.  Yandel’s solo studio album after the split, De Líder a Leyenda, was released in November 2013, which was certified Gold (Latin) by the RIAA in 2014.  

But after five years of being on their own, they reunited in February 2018, and four months later they did their first U.S. concert at Madison Square Garden. 

In May 2018, they did a concert at the José Miguel Agrelot Coliseum in Puerto Rico selling out the show quickly and resulting in adding more shows, totaling 8 back-to-back shows at this venue. 

Later that year they released Reggaetón En Lo Oscuro the lead single from their upcoming tenth studio album Los Campeones del Pueblo / The Big Leagues, which features collaborations with many artists including Ozuna, Maluma, and Bad Bunny.

Back on track, Yandel continues to make beautiful reggaeton music again with Winsin.

— Latin Heat News Service

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