He was a director in local, independent theatres Teatro de los Independientes and La Máscara during the 1950s and in 1958, received his first film role in Simón Feldman's El negoción (The Bargain).
[1] Gandolfo was not a prolific film actor, and his only significant roles were in Agustín Navarro's Una jaula no tiene secretos (A Cage Keeps No Secrets, 1962), and in Alejandro Doria's banned political satire, Proceso a la infamia (Trial on Infamy), which was made in 1974; but, released in an edited version four years later.
[2] He was, however, well known in Argentine theatre, where an ancestor, Juan José de los Santos Casacuberta (1818–49), had been a lead actor in its early days.
Gandolfo received leading parts in local productions of prominent works such as Medea, The Seagull, and Mother Courage and Her Children, during the 1950s and '60s.
Among his many stage productions were those of George Bernard Shaw's The Man of Destiny, Arthur Miller's A View from the Bridge and Tony Kushner's Homebody/Kabul.