The reflections composing its cycle were mostly written coterminously with the drafting phase of his doctoral thesis The Origin of German Tragic Drama, during his personally transformative though ultimately failed romance with Asja Lācis.

Greil Marcus compares certain formal qualities of One Way Street to the surrealist graphic novel Hundred Headless Women by Max Ernst and André Breton, or to Walter Ruttman's The Weekend which was an early sound collage film.

The book avoids, "all semblance of linear-narrative...[offering] a jumble of sixty apparently autonomous short prose pieces: aphorisms, jokes, dream protocols, cityscapes, landscapes, and mindscapes; portions of writing manuals, trenchant contemporary political analysis; prescient appreciations of the child's psychology, behavior, and moods; decodings of bourgeois fashion, living arrangements and courtship patterns; and time and again, remarkable penetrations into the heart of every day things, what Benjamin would later call a mode of empathy with 'the soul of the commodity'" according to Michael Jennings in his introduction to the work.

"[1] Particularly significant or frequently excerpted and collected segments from One Way Street include "Imperial Panorama-A Tour of the Inflation" (an essay on the social and psychological effects of the German hyperinflation written in 1923 and dedicated to Gershom Scholem upon his emigration from Germany to Palestine) and "To The Planetarium"(1928).

He enters the arena of the academic argument around ontology and the Theory of Categories according to the technical conventions and requirements of the university in his contemporaneously written "Epistemo-Critical Prologue" to The Origin of German Tragic Drama (though this work was rejected at his habilitation).