Aventura’s output in the 2000s was defined as much by its unpredictability as its ability to please giant crowds fueled by Romeo’s charm and Lenny’s electrified take on bachata’s arpeggiated riffs, Aventura took the genre even further in the 21st century as they duetted with reggaetón superstar Don Omar and electro duo Nina Sky, and honored their past by collaborating with giant Antony Santos.

The title wound up being prophetic: 2002’s We Broke the Rules expanded further on their vision of modern bachata with the smoldering “Obsesión” and a cover of *NSYNC’s 2001 hit “Gone” that showcased lead singer Romeo Santos’ sweetly cool croon.

Blending boy-band style and contemporary R&B’s smoothness with the snapping beats that define the guitar-forward, lovelorn Dominican genre, cousins Anthony “Romeo” Santos and Henry Santos and brothers Lenny and Max Santos declared themselves to be at the forefront of Generation Next with their 1999 debut. Formed in the Bronx in 1995, Aventura changed Latin pop by remaking bachata for the hip-hop era.

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