Daddy Yankee is often considered to be one of the pioneers within the Reggaeton genre. Ayala was originally going to become a professional baseball player but he was shot in his leg while taking a break from a studio recording session. The bullet was never removed and he credits this incident with allowing him to pursue a musical career. He first appeared on the 1991 DJ Playero’s Mixtape, Playero 34, with the song “So’ Persigueme, No Te Detengas”. His first official studio project as a solo artist was No Mercy, which was released on April 2, 1995 through White Lion Records and BM Records in Puerto Rico. Early in his career he attempted to imitate the rap style of Vico C. He went on to emulate other artists in the genre, including DJ Playero, DJ Nelson, and Tempo taking elements from their styles in order to develop an original style with the Dembow rhythm. In doing so, he eventually abandoned the traditional model of rap and became one of the first artists to perform reggaeton. Throughout the 1990s, Daddy Yankee appeared in several of DJ Playero’s underground mixtapes which were banned by the Puerto Rican government due to explicit lyrics; these songs would later be among the first reggaeton songs ever produced. DJ Playero and Daddy Yankee would later be credited for inventing the name “Reggaeton” to describe their music on the album Playero 36 in 1994.
In 1997, Daddy Yankee collaborated with the rapper Nas, who was an inspiration for Ayala, in the song “The Profecy”, for the album Boricua Guerrero. He released two compilation albums with original material: El Cartel (1997) and El Cartel II (2001). Both albums were successful in Puerto Rico, but not throughout Latin America. Between those years, Ayala released a total of nine music videos, including “Posición” featuring Alberto Stylee, “Tu Cuerpo En La Cama” featuring Nicky Jam, and “Muévete Y Perrea”.
In 2000, Daddy Yankee formed an unofficial duo called “Los Cangris” with Nicky Jam and released several successful singles together. Yankee and Nicky Jam fell apart in 2004 due to personal issues and creative differences. In 2012, Daddy Yankee and Nicky Jam reconciled and performed in various concerts together.
In 2002, El Cangri.com became Ayala’s first album with international success, receiving coverage in the markets of New York City and Miami with hits including “Latigazo”, “Son Las Doce”, “Guayando” and other songs like “Enciende”, which talks about different social problems of the era, mentioning corruption and religion.
In 2003, Daddy Yankee released a compilation album named Los Homerun-es, which contains his first charted single (“Segurosqui”), five new songs and 12 remakes of DJ Playero’s albums songs. that was later charted, “Seguroski”, being his first charted single after six of them.
In 2003, Ayala collaborated for the first time with the prestigious reggaeton producers Luny Tunes on the album Mas Flow, with his commercial success song “Cógela Que Va Sin Jockey” (a.k.a. “Métele Con Candela”), and Mas Flow