During the 1980s, he recorded "Homenaje a Eddie Palmieri" (Tribute to Eddie Palmieri) with the Puerto Rican All Stars. He also recorded with various orchestras, amongst them the Tommy Olivencia Orchestra, and the Willie Rosario orchestra. Santa Rosa developed a unique style of "soneo" (improvisation) in salsa that permitted him to be successful in both the "tropical" and "romantic" styles of the music. In 1986, Santa Rosa formed his own band and signed with Combo Records; a string of hits followed, such as "Good Vibrations", "De Amor y Salsa" (Of Love and Salsa), "Punto de Vista" (Point of View), "Vivir Sin Ella" (Living without Her) and "Perspectiva". Santa Rosa was also the first singer of tropical salsa to carry out a concert at the Carnegie Hall Theater, in New York City, where he performed as the opening number, his unique version of the salsa tune, "Represento" (I Represent), composed by Lou Briel. This event was recorded live at the hall, and later released as an album. A highlight of the night was the four-minute unscripted addition he made to his song "Perdoname" (Forgive Me), which solidified his improvisational talent. This live version became such a sensation thereafter that Santa Rosa had to memorize his own improvised lines for future concerts, and Perdoname became the closing song to his shows. In 1990, Santa Rosa joined the all star "La Puertoriqueña" project which included Andy Montañez; in the same year he was awarded the Billboard Lo Nuestro Award for Best Male Singer. He also participated in the play "La Pareja Dispareja" (The Odd Couple) alongside Luis Vigoreaux and Rafo Muñiz. In 1995, Santa Rosa traveled to Japan as Puerto Rico's Good Will Ambassador, where he sang "De Cara al Viento" (Facing the Wind) in Japanese. In 1996, the greatest hits album "Caballero de la Salsa, Vol 2" was released and he also participated in the First "Festival Presidente" in the Dominican Republic (a Latin music festival sponsored by local Presidente beer). In 1997, he sang with Andy Montañez in New York Citys Lincoln Center and later that year, with Olga Tañon at the Universal Studios Amphitheater in Hollywood, California.