In 1988, Tommy Olivencia heard Rivera sing alongside his father and recommended that he sing solo. When Rivera was 14, his father made a demo and presented it to the CBS music department. They signed Rivera.Rivera began to be known as "El Bebé de la Salsa" after recording his first album, Empezando A Vivir, . This project generated many hits  that became number one hits first in Puerto Rico, then among the Hispanic populations in the United States and finally across Latin America.His third album, Cuenta Conmigo won three Platinum Record awards in the United States, Puerto Rico, Venezuela and Colombia. It became the most-sold salsa album in history, a record previously held by Willie Colón, and held the number-one spot in the Latin American Billboards for three consecutive months.The introduction of Amores Como El Nuestro was sampled by Haitian-rapper Wyclef Jean in his 2004 song "Dance Like This" from the soundtrack of Dirty Dancing: Havana Nights which would later become the worldwide number-one 2006 hit "Hips Don't Lie" by Wyclef and Colombian-singer Shakira. However, in the case of Shakira, she was accused of plagiarism since she made the recording without Riveras consent.In 1993, he released Cara de Niño. In 1994, as his popularity was rising, he released his first compilation album, Lo Nuevo y lo Mejor and contained the single hit Me Estoy Enloqueciendo Por TiIn 2000, Rivera recorded Para Siempre This was his last album on Sony Latin records. In 2001, he released his self-titled album Jerry Rivera and the year after, he recorded Vuela Muy Alto which brought him a new fanbase all over Latin-America and the U.S., with the title track hit the top spot and the top 10 in many charts along with Herida Mortal (Mortal Wound). The following year he returned to his salsa roots and released Cantando A Mi Idolo... Frankie Ruiz a tribute album to one of his idol Frankie Ruiz. The album gained him a Latin Grammy nomination, made up for the poor sales of his previous ballad albums, and his major album hit was Ruiz's Mi Libertad featuring Voltio.