Ilya Mashkov expresses a shocking and rebellious sentiment with Self-Portrait and Portrait of Pyotr Konchalovsky (1910), which was a defining manifesto of the early Russian avant-garde, especially that of the "Jack of Diamonds" group. The painting is a dual portrait of Ilya Mashkov and his close friend and artistic collaborator, Pyotr Konchalovsky. Rather than presenting themselves in an academic manner, wearing the traditional dignified clothing expected of academic masters, both figures are depicted in nearly nude state, wearing only black athletic trunks. The figures have exaggerated musculature (as if mimicking the bodies of circus strongmen or weightlifting champions) and display inflated biceps and rigid stances that emphasize their bodies as an expression of raw, physical power. The items surrounding the two men create an interesting juxtaposition of high culture and low-brow, earthly materiality. On one side of the room is a table filled with everyday items of low culture (teapot, cup, etc...), while on the other side, the intellectual and artistic world is represented by a piano, a violin held by Mashkov and sheets of music held by Konchalovsky. Additionally, the spines of art monographs focusing on Giotto and Paul Cézanne (the two most influential structural and stylistic figures for these young artists) are clearly visible as part of the background on a bookshelf.

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