Using historically-chronological, comparative and textual methods and elements of reconstruction of the plays, we analyze common and different approaches of Latvian and Ukrainian theatres to the production of works in the genres of a musical and rock opera. The given examples combine the adventurous issues and the character of the protagonist in the theatrical performances of both countries. The chronology of the study covers largerly the performances produced during the years of Latvia’s and Ukraine’s independence. Having analysed separate musically dramatic performances of various genres presented on the stages of Riga, Liepāja (Latvia), Odessa and Kyiv (Ukraine) theatres, we can see that they all address Christian symbols and have a motif of salvation of a charming, charismatic sinner through love. The main difference between the approaches of theatres of the two countries to the implementation of musicals, zong-operas, rock operas is that Latvians succeed each time, creating significant for the generation works and performances based on their own national material. Every time Valdis Lūriņš’ productions, which impress with turning some moments of Latvian history into epic ones, become a major event in the musical and theatrical life of Latvia, as was “Lāčplēsis” in 1988 and “Kaupēns, My Dear!” in 1999. The most important musicals and rock operas produced by the Ukrainian theatre are associated with the development of Western European repertoire (“The Threepenny Opera”, 1968, directed by Мatvei Osherovsky and “The Threepenny Love” based on Bertolt Brecht’s play, 1996, directed by Еdward Mitnitsky — both of them were produced by Odessa Academic Musical Comedy Theatre; “The Threepenny Opera”, 1966, directed by М. Sokolov, Kyiv National Operetta Theatre) and Russian drama (“Krechinsky’s Wedding (A Game)” by Alexander Коlker, 1974, directed by Е. Mitnitsky, Kyiv National Operetta Theatre) and tend to be more sentimental. In the Latvian performance “Liliom” of the early 1970s the adventurism of the hero was perceived as his romantic rebellion against the philistine world (similar to the illusions of the intelligentsia of the “sixties”), the hero of Ģirts Jakovļevs excited sympathy and even admiration. Instead, in the new conditions of the market economy of Latvia and Ukraine the hero of the performances of the 1990s, “The Threepenny Love” and “Kaupēns, My Dear!”, remained unmourned. If in the Odessa production Macheath (Vladimir Frolov) was respected at least for intellectualism of maxims about “cruelty of life”, then in the performance of the Liepāja Theatre, catharsis paradoxically struck the audience not because of the death penalty of the main character, but because the circumstances forced the Poet-Humanist (Zigfrīds Muktupāvels) in love to become a tyrant.