The article presents, for the first time, an attempt to reconstruct the context and the object of creative contacts of Vasily Zhukovsky and Friedrich Wilhelm von Schadow (1788–1862), a theorist of painting and head of the Academy of Arts in Dusseldorf. The sources for the reconstruction were the previously unpublished eight letters by the German artist written in the period from 1838 to 1846 and now stored in the Manuscript Department of the Institute of Russian Literature and materials from the creative heritage of the Russian poet and artist. The article establishes new facts about the institutional role of Zhukovsky in the Russian-German cultural ties in the 19th century. Von Schadow gave some of his paintings in the original, in copies or prints for Zhukovsky’s personal collection and for the imperial collection of the future Hermitage. The list of these paintings is, for the first time, compiled in the article. The textual material is illustrated with images from von Schadow’s works discussed in the epistolary dialogue. Von Schadow’s published manifestos on the theory and criticism of Christian religious painting, which Zhukovsky read and which influenced his artistic worldview in the 1840s, are attributed. The article presents, for the first time, the most significant fragments from von Schadow’s letters of 1838–1845 translated into Russian. The fragments fill in the gaps in the objective representation of the scale of Zhukovsky’s activities at court on compiling a collection of Russian paintings both in the institutional and ideological artistic aspects. At the same time, the communication between the German artist and the Russian poet found reflection in Zhukovsky’s creative heritage of the late period: in his criticism, works on art theory, prose, and reflections. Von Schadow, in his last letters, and Zhukovsky, in his diary entries, pay special attention to reflections on pedagogical activities and works on the theory of fine arts, as well as on their social and political activities. The parable of the prodigal son was the final touch in the creative dialogue of the poet and the artist. Zhukovsky reflected this parable in his unfinished poem about the Wandering Jew. The lines of the poem paint in words fragments from the Sacred History quite in the spirit of von Schadow’s paintings: Zhukovsky compares the Wandering Jew who ascended Calvary with the prodigal son and depicts the holistic canvas of the inner and outer space of the character through his eyes. The conclusion is made that the discovered letters from von Schadow to Zhukovsky reveal the adherence of the both to the lofty romantic idea of a synthesis of arts based on the poetics of heartfelt feelings, artistic imagination, active teaching, and religious and mystical experience. Fine arts, science and history, issues of faith and politics of the mid-19th century were a background for the concentration of the correspondents on the rethinking of substantial religious and philosophical issues on the material of eternal biblical plots on the entombment of Christ, taking Christ down from the cross, on reasonable and unreasonable maidens, and, finally, on two parables about the lost sheep and the prodigal son, which became the ultimate embodiment of the dialogue of a poet and an artist in fine arts.