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Since 1914 Wesselowsky was a member of the Moscow Sinodal Chorus. During the First World War he served as an Officer. He started his career in 1917 at the Moscow Bolshoi Theatre. In 1920 he appeared in ''La fille de Madame Angot'' of Charles Lecocq. In 1921 together with cellist Gregori Pyatigorsky and violinist Mikhakov, he went on tour in the cities of West Ukraine. With them he arrived in Romania. Then has emigrated to France, where he made his debut at Opera Comiqueas Wilhelm Meister in ''Mignon''. In France he appeared also in performances of Paris Russian Opera. In 1920s he sang at the opera house of Belgrad. Then in Barcelona (Teatro Liceo, 1922), Buenos Aires (Teatro Colon, 1924). In 1925 Wesselowsky went to Italy to study. In the same year, by the invitation of Arturo Toscanini, he made his debut at La Scala, Milan as Vasily Golitsyn in ''Khovanshina''. He sang at La Scala up to 1950 appearing in ‘’Prince Igor’’, ‘’Khovanshina’’, ’’Manon Lescaut’’, ‘’Fedora’’, ‘’Traviata’’, ‘’Lohengrin’’ etc. Wesselowsky also made guest appearances in Paris (Grand Opera 1926, 1938). He sang with success in different italian opera houses. Performed in many opera premieres at La Scala ("Il Dibuk", ‘’Nerone’’, "La Flamma"). After his retirement he taught singing in Milan. Wesselowsky made records for Pathe, Columbia and Brunswick.
Chronology of some appearances
1924 Buenos Aires Teatro Colon Madama Butterfly (Pinkerton)
1924 Buenos Aires Teatro Colon Mefistofele (Faust)
1924 Madrid Teatro Reale Madama Butterfly (Pinkerton)
1925Lisbon Coliseo Recrejos Barbiere di Siviglia (Almaviva)