After various professional experiences in the world of opera as voice technician, artistic and production director, Riccardo Canessa was assistant director at the Arena di Verona in the summer of 1998, participating in the stage design of Rigoletto, Nabucco, Un Ballo in maschera, Aida and Tosca. Subsequently he worked in the same position for Siegfried at the Erl Festival, and for La Bohème at the Teatro Regio in Parma.
At the same time he began working as a director for operas such as Rigoletto at the Coliseum in Lisbon, Otello in the United States, Tosca in France and La Bohème in Lucca, Pisa, Livorno and Mantua.
He made his debut at the Teatro Filarmonico in Verona in November 1999 with La Traviata.
Subsequently he worked on Tosca in Salerno, Carmen in Padua, Il Barbiere di Siviglia, Don Pasquale, Cavalleria rusticana and Pagliacci in Adria.
In 2001 he was invited to Spain for different performances of Rigoletto, and made his debut at the Marseilles Opera with I Lombardi alla prima crociata, he then worked on the stage designs for La Serva padrona in Veneto and L'Elisir d'amore in Orvieto.
In 2002 he returned to Marseilles with another two titles: Macbeth and Don Chisciotte, the latter was also performed in Nice. He then received personal success at the Teatro Regio in Parma with the diptych La Clochette by E. R. Duni - Il Campanello by Donizetti.
Following L'Elisir d'amore at the Teatro Filarmonico in Verona, he abandoned Donizetti's buffo repertoire for a while to return to Parma where he directed Macbeth for the Fondazione Toscanini.