Early musical career
Calderón's career began as a participant in Puerto Rican hip hop contests on television during the 1990s. He met Eddie Dee and DJ Adam who would become his main collaborators, but Calderón was rejected by most producers and deejays at the time. DJ Adam in an interview with Puerto Rican podcaster Chente Ydrach said that Calderón was going to be a part of the underground album DJ Adam's Mad Jam, but Calderón's style was too eccentric and underdeveloped, so he was taken out of the final tracklist.
Calderón signed to Eddie Dee's label in 2000, collaborating with Dee on his first hit on Puerto Rican radio, the hip hop song "En Peligro de Extinción" from Dee's second album El Terrorista de la Lírica.
During 2001-2002, Calderón participated in over a dozen original compilations including gold and platinum albums such as "Kilates", "Boricuas NY" volumes 1 and 2, "The Majestic", "La Mision" volumes 2 and 3 and of course his first worldwide crossover hit 'Cosa Buena' from the "Planet Reggae" production distributed by White Lion Records and Diamond Music. On top of that, he also was featured in the albums of Yaga y Mackie "Sonando Diferente" and Maestro's "The Movie" which further accelerated his buzz in the streets.
Thanks to 'Cosa Buena' and it being one of the first reggaeton videos receiving major rotation on mainstream channels such as Telemundo, in 2002, Calderón became a worldwide phenomenon before his debut album "El Abayarde" in November of that same year creating much hype for his debut. Despite only being available in Puerto Rico, the Dominican Republic and parts of the United States due to White Lion Records (formerly known as Boricua Guerrero and now 100% under Elías de León's ownership) being an independent label at the time; Regardless, 'El Abayarde' became the first hip hop/reggaeton album by a solo artist to sell over 75,000 units in one week with no major label distribution. This success led to Calderón and White Lion signing a joint venture with Sony Music Latin. Calderón formed his own label in the process known as Jiggiri Records under the White Lion banner and distributed by Sony Music Latin. Jiggiri Records would go on to sign and release multi-platinum albums from notable artists such as Zion & Lennox, Julio Voltio and John Eric. Calderón would go on to become one of the most successful touring acts in all of Latin music from 2003-2005, thus further legitimizing the genre now known as reggaeton (once called 'underground').
In August 2003, Calderón performed at the Madison Square Garden in New York City. Based on his show and performance, The New York Times noted that he "made the best case for Reggaetón as music with room to grow" being a "forward-looking performer." His second appearance at the venue was in October 2004, where he headlined an event titled Megatón 2004. The concert sold out, with 20,000 in attendance, a mixed crowd of Latino and non-Latino fans.
Calderón's travels subsequently led him to Miami, where he incorporated dancehall elements into his musical style. In 2004, his album titled El Enemy de los Guasíbiri was released. The album's production included a mix of several urban genres. Calderón claimed that he preferred the influence of these other genres due to his belief that Salsa had "become too corporate and too safe". Years after its release, Calderón stated that he had never approved the release of the Guasibiri album, which he claimed was rather a collection of old songs and that it should be left out of his discography as an unauthorized album. Following the release of this album, reggaeton gained more influence with several hip-hop producers in New York. Calderón continued working on several mixtapes, being featured in remixes of Usher's "Yeah", Fat Joe's "Lean Back", N.O.R.E.'s "Oye Mi Canto" and Akon's "I Wanna Love You", 50 Cent's P.I.M.P remix and also Calderón featured Aventura's "We Got the Crown".
