In 2000, Rivera recorded Para Siempre ('Forever'). Jerry sang the song with his father at the Roberto Clemente Coliseum in San Juan.
In 1999, Rivera recorded De Otra Manera ('Another Way'), his first attempt at ballad music, which featured the bolero Ese ( Him). Ya No Soy El Niño Aquel was released in 1997. The following year, "Magia" was released with the self-titled album and Ahora Estoy Solo ( Now That I'm Alone) In 1996, Rivera released "Fresco" and Una y Mil Veces (One Thousand and One Times) and Lloraré ( I Will Cry) were the album hits. In 1994, as his popularity was rising, he released his first compilation album, Lo Nuevo y lo Mejor (The New and the Best), and contained the single hit Me Estoy Enloqueciendo Por Ti ('I'm Going Crazy For You'). In 1993, he released Cara de Niño ('Baby Face') with ¿Qué Hay De Malo? ('What's Wrong About This?'), Cara de Niño, No Hieras Mi Vida as being major hits of the year.
The introduction of "Amores Como El Nuestro" can also be heard on MTV's animated series Daria episode "Fair Enough' of its second season. The introduction of Amores Como El Nuestro has been sampled twice in hip hop, first by American East Coast hip hop duo Lord Tariq & Peter Gunz, also used as the introduction for their 1997 song " Deja Vu (Uptown Baby)", and 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. Rivera was awarded two Premio Lo Nuestro Awards for "Singer of the Year" and "Album of the Year" and Sony Records presented him with three Crystal Awards. The number one hit for the album was Amores Como El Nuestro (written by Panamanian songwriter Omar Alfanno) (Love like ours) which is considered to be the best song by Rivera. Its hit songs included the Cuenta Conmigo, Me Estoy Enamorando ('I'm Falling in Love') and Casi Un Hechizo (Nearly A Charm). 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. His third album, Cuenta Conmigo ('Count on Me'), won three Platinum Record awards in the United States, Puerto Rico, Venezuela and Colombia. His second album, Abriendo Puertas ('Opening Doors'), produced the hit songs Esa Niña ('That Girl'), Dime ('Tell Me'), Nada Sin Ti ('Nothing Without You'), and Como un Milagro ('Like a Miracle') became number one hits first in Puerto Rico, then among the Hispanic populations in the United States and finally across Latin America. This project generated the hit, De La Cabeza A Los Pies ("From Head to Toe"). Rivera began to be known as "El Bebé de la Salsa" (the baby of salsa) after recording his first album, Empezando A Vivir. When Rivera was 16, his father made a demo and presented it to the CBS music department.
In 1988, Tommy Olivencia heard Rivera sing alongside his father and recommended that he sing solo. In 2003, this picture was used by Rivera to make the album cover for his tribute Canto a mi Idolo. Frankie Ruiz, who was a guest at the hotel, appeared and sang a couple of songs with them and had his picture taken alongside Rivera. In 1986, when he was 13 years old, he accompanied his father who was performing at a hotel in Isla Verde, San Juan. His parents, also musicians, inspired him to become a musician and as a child he would often accompany his mother Dominga, a singer, and father Edwin, a guitarist and director of Los Barones Trio, during their shows.
Two other brothers, Ito and Jose, are professional instrumental musicians. His entire family consists of musicians, including tropical recording artists Edwin Rivera and younger sister Saned. Rivera (birth name: Gerardo Rivera Rodríguez ) was born in Humacao, Puerto Rico, a town located on the eastern coast of Puerto Rico, moved with his family to Levittown in the town of Toa Baja, where he received his primary and secondary education.