He began his musical career in 1996 (as Tego Tec) and was supported by the famous Puerto Rican rapper Eddie Dee, who invited him on his second studio album, El Terrorista de la Lírica, released in 2000.

Calderón reached international success in 2003 with his first album, El Abayarde, which sold 300,000 copies worldwide and was nominated for a Latin Grammy Award.

He released three more studio albums between 2006 and 2015, varying in styles, focusing more in hip hop and African music rather than reggaeton in The Underdog/El Subestimado (2006) and El Abayarde Contraataca (2007).

He is the son of Pilar Rosario Parrilla, a schoolteacher, and Esteban Calderón Ilarraza, a government worker for Puerto Rico's Department of Health.

He eventually developed a music style that combined elements of salsa, plena, dancehall, and hip-hop, focusing on aspects of urban life in his lyrics.

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.

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, Voltio and John Eric.

'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".

.. steered his country's dominant youth culture out of the island and Latino neighborhoods, and into the American stream of pop consciousness.”[5] Around this time Calderón still remained a fixture in popular Latin music thanks to international hit such as the Don Omar– led "Bandoleros" (notably included in The Fast and the Furious: Tokyo Drift soundtrack) and "Quítate Tú Pa Ponerme Yo" from Dee's 12 Discípulos compilation album.

This album featured appearances by Buju Banton, Voltio, Bataklán, Eddie Dee, Luis Cabán, Yandel, Zion, Chyno Nyno, Don Omar and Oscar D'León.

[11][12] On The Underdog/El Subestimado, he collaborated with rap duo Anónimo Consejo to create a song entitled "Son Dos Alas" which eventually was shortened to an interlude without Calderón.

The most prevalent themes among his music, videos, and interviews are the commemoration of blackness and exposition of racism against Latino and Latin American individuals.

[2][16] Calderón turned down roles in both Feel the Noise and "El Cantante" and instead chose to appear in Illegal Tender out of respect for its producer.

The documentary focused on the role of Hip Hop in the blood diamond trade, after the filming concluded Calderón publicly announced that he would no longer wear jewelry.