The paper is concerned with G. Obolduev, one of Russia’s most prominent poets of the first half of the 20th c., whose works are only now returning to readers. The poet’s first collected poems were published in 1991 thanks to L. Ozerov, who compiled the collection. Since then, Obolduev has inspired numerous works, but the research would normally focus on his mature and later lyrical works. By contrast, this article looks at the poet’s earlier work, typified by examples of language play, metaphorical convergence of opposing concepts, omission of links in chains of free associations, and so on. Especially interesting are quotes from the reminiscences of the children’s writer E. Blaginina, the poet’s wife, which offer an insight into Obolduev’s creative process and characteristic way of thinking, as quite a few of his earlier poems plainly require a detailed, almost line-by-line, commentary, such as the one provided by the authors of this article.