Raised by his mother in Guaynabo, Puerto Rico, Crespo served a long apprenticeship from the age of six, launching his career in 1988 as a member of the Willie Berrios Orchestra and six years with the Toño Rosario Orchestra. Leaving Rosario's group in 1994, Crespo briefly attended the Metropolitan University of Puerto Rico, where he studied business administration. An invitation to join Grupo Mania, however, was too tempting to resist. Agreeing to join the popular Latin band, he wrote and sang on their hit "Linda Es." He left the group after three years to focus on his solo career.
The gamble paid off. His 1998 effort, Suavemente, topped the charts and found large audiences in Miami and New York as well as the Caribbean. The album earned him four Premio Lo Nuestro awards, the Billboard award for Best Male Tropical/Salsa Album, and a place on the Billboard Latin albums charts for 96 weeks. He followed suit with 1999's Pintame, which won a Grammy for Best Merengue Performance and firmly established his place in Latin music.
Crespo toured almost constantly, and appeared on television and in films. His next offering was 2000's Wow Flash. In 2001, he participated in the all-star benefit recording "El Ultimo Adios" for the victims of the September 11 attacks on the World Trade Center in New York. 2002's Urbano kept him at the forefront of the merengue audience but was his last album for Sony. While 2005's Saboréalo (issued on Ole) didn't scale the same sales heights as his previous offerings, it did net him a Latin Grammy Best Merengue Album. In 2007, Crespo shifted gears. He left Ole for Machete, and released Regresó el Jefe. It showcased nine of his own compositions and immediately catapulted him back to the limelight in the Americas. The single "La Foto Se Me Borró" may have been a merengue tune, but the album also showcased bachata and urban styles amid his swinging mambos. The album topped the Latin Albums and Tropical Salsa charts and was nominated for a Latin Grammy; it subsequently won four Premio Lo Nuestro awards. Following a live album, Crespo returned to Sony briefly via its Nulife imprint and released Indestructible in 2010. It landed in the Top Ten of both the Latin Album and Salsa charts. On this set, the merengue hooks collided head on with driving salsa and bachata beats. Crespo re-signed to Machete and issued Live from Las Vegas in 2011. It was simply a stopgap before his next big shift, as he concocted a seamless blend of merengue, urban, salsa, and Latin pop for 2012's Monsters. For 2013's One Flag, he leaned heavily on hard-driving urban pop and big production salsa as his merengue evolution continued toward club audiences. Pitbull appeared on the track "Sopa de Caracol." For 2015's Tatuaje, Crespo looked all the way back to the heart of the merengue tradition -- albeit with some modern production touches. With rich, swinging horns, joyous backing choruses, and layers and layers of organic rhythms and piano montunos, the album marked a creative return to the artist's place of origin. After a world tour, Crespo took a breather and, when he entered the studio, flipped his own script. 2018's Diomedizao was a tribute to Colombian singer/songwriter Diomedes Diaz. Crespo first heard his music in 1999 and was drawn in initially because his father's nickname is "Diomedez" while his mother's last name is "Diaz." More than this, he watched a dramatic television bio series on the songwriter and was deeply moved by his story. To that end, he cut eight vallenato and cumbia songs with a tropical merengue twist led by the charting single "Ella Me Beso," releasing it in the winter of 2018 and following it with a tour. ~ Craig Harris, Rovi