2000s
Santa Rosa's hits continued with the album "Expresion" which included the single "Fulana" (What's her name) and in 2001 with the album "Romantico". He released "Viceversa" in 2002 which became a "hit" in the Latin community in the United States and in all of Latin-America.
Santa Rosa has taken on himself the task of keeping Tito Rodríguez's musical legacy alive and has acquired much of Tito's memorabilia, including articles of clothing, music and furniture from his home in Puerto Rico. Santa Rosa has staged several concerts and dances honoring the late singer, and recorded an album of his where with the use of modern technology, he sings "En la Soledad" (In Solitude), composed by Puchi Balseiro in a duet with him . During the week of February 24, 2003 Santa Rosa organized a two-night concert at the Center of the Performing Arts in Caguas, Puerto Rico. As an introduction to the event, he arranged for his private collection of Tito Rodríguez memorabilia to be exhibited in the lobby of the center. In 2004, he released "Autentico".
In addition, he has long played an important role in the career of his friend and protégé, Víctor Manuelle, who Santa Rosa discovered. The two released a joint live album late in 2005, "Dos Soneros, Una Historia." In 2006, he released, "Directo Al Corazon", and in 2007 he carried out a concert acknowledged by the critics, in Plaza Colón at Santo Domingo and released Contraste with Conteo Regresivo being a major album hit. Furthermore, he performs alongside Chucho Avellanet, a musical comedy club-act called, Cantando y Contando, (Singing & Telling Stories), throughout the island.
On February 9, 2008 Santa Rosa participated in an event named "Concierto del amor" which was organized in the Madison Square Garden. In June 2008, "Contraste" received Gold and Platinum certification from the Recording Industry Association of America. According to the organization, the production has sold over 1,500,000 copies. At the moment of certification, the album's first single "Conteo regresive" had been sixteen weeks in the first place among Billboard's tropical list. Meanwhile "No te vayas" began gaining positions in the same list. After participating in New York City's Puerto Rican Day Parade, Santa Rosa prepared to begin an international tour beginning on June 13, 2008, in New Orleans before proceeding to Tampa, Florida, Ecuador, Chile, Spain, Colombia and Mexico. The concert in Chile, on June 28, 2008, was Santa Rosa's first ever in said country. the event took place in the Caupolicán Theatre and was attended by approximately 8,000 fans. On July 5, 2008, Santa Rosa became the first salsa singer to perform at the Palau de la Música in Barcelona. The event was a Sold Out, filling the venue with an attendance of 2,000. Santa Rosa was selected to perform at the "Balón de Oro" award ceremony, the most important condecoration in Mexican Football. Santa Rosa was selected to take part in "La Nueva Salsa", where he would perform along several young salsa artists. Santa Rosa has also contributed to improving Puerto Rico's public education system. He participated in Sapientis Week, an initiative sponsored by the non-profit Sapientis which brings distinguished public figures into classrooms in order to raise the public's awareness of the education crisis in Puerto Rico. On July 17, 2010, he participated in the opening ceremony of the 2010 Central American and Caribbean Games.
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