When he was nine years old he accompanied his mother to have her eyes tested and, hearing someone singing from another room, he spontaneously began his own rendition of "Ave Maria".

At age 13 he played the Pastorello in a performance of Tosca at Teatro dell'Opera di Roma,[1] where he shared the stage with Luciano Pavarotti.

[1] Grigolo made his debut at the Royal Opera House in 2010 as Des Grieux in Manon, going on to sing Faust, the Duke in Rigoletto, Rodolfo in La bohème, Nemorino in L'elisir d'amore, Werther, and Cavaradossi in Tosca.

[4] Giuseppe Verdi: Don Carlo, I Due Foscari, Un Ballo in Maschera, Luisa Miller, Messa da Requiem, Rigoletto, La Traviata, Il Corsaro; Gaetano Donizetti: L´Elisir d’Amore, Don Sebastiano, La Favorita, Anna Bolena, Lucrezia Borgia & Lucia di Lammermoor Giacomo Puccini: La Bohème, Tosca, Madama Butterfly; Charles Gounod: Faust, Roméo et Juliette; Gioachino Rossini: Petite Messe Solennelle, Stabat Mater; Wolfgang Amadeus Mozart: Idomeneo, Così fan tutte; Jules Massenet: Werther, Manon; Leonard Bernstein: West Side Story; Jacques Offenbach: Les Contes d’Hoffmann;[5] The European Commission of the EU granted Grigolo and Romano Musumarra a European Border Breakers Award, along with the record company, authors and publishers, for recording the highest sales for a debut album in 2006 within the European Union, but outside of its country of production.

Grigolo plays Cassio in Giuseppe Verdi Otello recorded at Gran Teatre del Liceu Barcelona 2006