Caetani considers Nadia Boulanger to be the driving inspiration of his career. She discovered his talent, initiated him into music, and gave him the philosophical approach to life linked to Montaigne, that he still has today.

At the Rome Conservatory of Santa Cecilia, he attended Franco Ferrara's conducting class and studied composition with Irma Ravinale. At the age of 17, he made his theatre debut with a production of Monteverdi's Il combattimento di Tancredi e Clorinda and other madrigals that he arranged himself. After studying all the Shostakovich Symphonies with Kiril Kondrashin at the Moscow Conservatory, he graduated with Ilya Mussin from the St. Petersburg Conservatory. Winner of the RAI Turin competition and Karajan Competition in Berlin, he started his career at the Berlin State Opera Unter den Linden” as repetiteur and assistant of Otmar Suitner.

Caetani’s vast experience, of almost forty years now, in the opera repertoire of Verdi, Puccini, Mussorgsky and Wagner (including several Ring productions) has influenced his approach to the great operatic and symphonic works of the twentieth century. Oleg was chief designate at the ENO in 2005, chief designate 2002-2005 for the Melbourne Symphony Orchestra and Music Conductor and Artistic Director for the same orchestra from 2005 to 2009. Before that, Caetani was the Principal Conductor for the Staatskapelle Weimar, First Kapellmeister of the Frankfurt Opera and GMD in Wiesbaden and in Chemnitz.

Since 1999, Caetani has had a particularly close relationship with laVerdi Orchestra and with them has toured South America (2003), Spain (2009), as well as three concerts in Salzburg (Schumann Symphonic Cycle) in February 2016.  In April 2008, he conducted the Orchestra Sinfonica di Milano in a concert presented by the Italian President to Pope Benedetto XVI in the Vatican, which was recorded live for Eurovision TV.

Shostakovich’s music plays a central role in his repertoire. Caetani translated the libretto of The Nose from Russian into German for his production in Frankfurt in 1991; he conducted the Italian premiere of the operetta Moscow Cheriomushki in 2007, and has conducted the first performances in many different countries of Shostakovich’s operas, concertos, ballets and suites, as well as having recorded the first Italian complete cycle of Shostakovich symphonies with the LaVerdi Orchestra in Milan. The CDs have won several prizes: 10/10 from Classical Today in the US, ffff Télérama in France and Record Geijutsu in Japan. His recordings of  Tansman’s symphonies, released by Chandos, won three Diapason d’Or in 2006 and 2008; his Gounod's Symphonies for CPO (including the 3rd Symphony discovered by Caetani) also won a Diapason d'Or in January 2015.

In 2001, he made his debut at La Scala in Milan with Turandot, returning there in 2005 to conduct Otello.  He opened the 2001 season of the Theatre of the Maggio Musicale Fiorentino with Don Pasquale. Recent engagements have included Khovanchina, Vaughan Williams's Sir John In Love, Madama Butterfly, La Bohème and Tosca, all at the English National Opera, The Flying Dutchman at the Teatro dell'Opera di Roma, L’enfant et les sortilèges at the Théâtre des Champs-Élysées in Paris, La Voix Humaine coupled with The Bluebeard Castle, Don Carlos in Cologne, Madama Butterfly in Berlin and Oslo, his debut at the Royal Opera House, Covent Garden with Tosca, Lady Macbeth of Mtsensk at the Oslo Opera, Tosca  at  the São Paulo Opera House, Tosca and Turandot at the Mariinsky Opera House, The Prisoner by Dallapiccola with the Mariinsky Orchestra during the Stars White Nights Festival, Lady Macbeth of Mtsensk in Helsinki, Les Pêcheurs des perles and Così fan tutte in Trieste and Otello in Weimar.

He regularly conducts orchestras such as the Staatskapelle Dresden, Munich Philharmonic, the Bavarian Radio Symphony Orchestra, Leipzig's Gewandhausorchester, the Wiener Symphoniker (with which he recorded Poliuto by Donizetti for EMI-CBS), Bamberger Symphoniker, Orchestre National de Radio France, the Mozarteum Orchester, Konzerthaus Orchester Berlin, RAI National Symphonic Orchestra, the Accademia di Santa Cecilia, the Maggio Musicale Fiorentino, Orchestra of the Teatro Verdi in Trieste, Orchestre Philharmonique de Monte Carlo, the Spanish National Symphony Orchestra, the Hong Kong Philharmonic, Metropolitan Symphony Orchestra, Sydney Symphony, Yomiuri Orchestra, Tchaikovsky Symphony Orchestra, Taipei Symphony Orchestra, the Berner Symphonieorchester, Orchestre Philharmonique de Strasbourg, the Qatar Symphony Orchestra, Montreal Symphony Orchestra and others.

Recent and forthcoming engagements include Carmen in Trieste, Cavalleria and Pagliacci at the Massimo Bellini in Catania, The Magic Flute in Tokyo and concerts with the London Philharmonic Orchestra, the Lucerne Symphony Orchestra, the Shenzhen Symphony Orchestra, Sydney Symphony, Metropolitan Tokyo Symphony Orchestra, the Orchestra Sinfonica di Milano (with which, in 2019, Caetani has celebrated an uninterrupted artistic relationship of 20 years), the Orchestre Philharmonique de Nice, the Orchestra da Camera di Padova e del Veneto, Symphony Orchestra of India, Würth Philharmonic and others.

He has also been a mentor to many young conductors he discovered, including Lorenzo Passerini, Michele Scotti, Beatrice Venezi, Maxim Rysanov, Charlotte Politi, and Luca Franzetti.

Future engagements include concerts with La Toscanini, performances in Wrocław, a China tour, and the release of Tchaikovsky’s Violin Concerto with Charlie Siem and the Philharmonia Orchestra.

Felsner Artists represents Oleg Caetani in German-speaking Europe, in co-operation with OnlyStage.