The article examines four films of late Soviet cinematography: “The Hat” (1981), “We Are from Jazz” (1983), “When the Saints Go Marching In” (1990), and “Taxi Blues” (1990). At the centre of the plots of all these films are characters with a passion for jazz. The study aims to trace, through the evolution of the image of the jazz musician, important patterns in the reflection of late Soviet cinema on the fate of the marginalised individual, especially relevant in light of the rapidly changing social landscape of the era. The general leitmotifs of the selected films are analyzed along two thematic directions: 1) psychological leitmotifs in the image of the hero-jazzman and 2) features of the soundtrack. Two ways stand out in the psychological portrayal of jazz musicians: creating group and individual portraits. In the group portrait, the image of the jazzman prevails adventurous nature, and passion for new and is not encouraged by the art from abroad. In more individualized portraits of jazz musicians, the personal drama, the hero’s strongest rupture with society and himself, caused by the impossibility of full professional self-realization, takes the upper hand. Although true film jazzmen dislike popular music, authors of films about jazz musicians strive to make a soundtrack designed for the general public. “The Hat” draws on rock and pop, “We Are from Jazz” stylizes Dixieland, and “When the Saints Go Marching In” uses famous jazz standards.