Calderón made several cameo appearances on other rapper's albums, eventually signing with label White Lion. In 2002, after three years of voice training, he published his first full-length album titled El Abayarde. Despite the fact that Reggaeton was considered an underground genre, the album sold 50,000 copies upon its release, setting a sales record for an urban music album. Three months after publishing El Abayarde, Calderón organized his first concert, which took place at the Roberto Clemente Coliseum in San Juan, Puerto Rico and sold out the venue. The following day he became the first rap artist to perform at the annual Puerto Rican Día Naciónal de la Salsa (National Day of Salsa).

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" and also Tego featured Aventura's "We Got The Crown".