Calandrelli's mother was a skilled pianist. Both his father and grandfather were medical doctors and expected him to follow their path. At age 4, Calandrelli started playing the piano by ear and took lessons at age 8.
In his late teens, with both of his parents' support, Calandrelli traveled to Europe to pursue a career in music. He arrived in Los Angeles in 1968 and collaborated with composer and arranger Clare Fischer. Inspired by him, Calandrelli decided to go back to Argentina and continue honing his skills.
He later returned to the United States with recommendation letters from the record labels he had worked with in Argentina. He recorded Russian-American conductor Andre Kostelanetz and a 65-piece orchestra at CBS' studio in New York.[4]
Calandrelli's work with Bennett includes twelve recorded albums, six Grammy Nominations and two Grammy Awards won.[9] Bennett's 2011 album "Duets II", arranged and conducted by Calandrelli debuted at No. 1 on the Billboard 200, Jazz Albums and Traditional Jazz Albums charts. This same No. 1 debut was achieved by Bennett's 2014 collaborative album with Lady Gaga "Cheek to Cheek", also arranged and orchestrated by Calandrelli.[10]