In mid-XIX century mechanical reproduction of images through lithography and photography becomes increasingly available — it allows for visual entrepreneurship on a growing scale. In literary artists this trend causes skepticism but in some (like O.W. Holmes) it also inspires creative interest. That the interaction between commercial and technological practices could be productive of aesthetic insight is proved by Walt Whitman’s poetic experiment. Whitman was fascinated by the art of photography – for a daguerreotype he would sit often, willingly and self-consciously, thus turning a portrait into an auto-portrait. Most of the editions of Leaves of Grass contain the author’s images, while Whitman’s form, the very principles his world-building imagination can be best understood through “photographic logic”. Two versions of the poem My Picture Gallery (the one dating back to mid-1850s and the one published in 1881) are being analyzed as instances of Whitman’s lifelong reflection on how the image, the world and the human subject interact. This relationship is full of submerged drama: technical reproducibility makes the image strikingly lifelike but also contributes to the “derealization” or “virtualization” of the world — tends to empower the subject but also to disable one through “the terrible doubt of appearances”. The visual analogue of the “catalogue” technique, representative of Whitman’s early manner, may be a sequence of snapshots and / or that of imperative pointing gestures: see, watch, imagine! Manicules are often used in Whitman’s early manuscripts: this typographic sign (described as “hand” or “printer’s fist”) is pervasive in newspaper advertising of the poet’s time and of particular interest to him — most probably, because giving a sense of forceful, embodied presence, direct contact with the world and the reader alike. In later editions the gesture gets a different representation — a butterfly rests, distractively, upon the index finger using it as a momentary landing grund. This image — Whitman’s newly chosen visual brand – is expressive of the contemplative attitude, indeterminacy and suggestiveness increasingly of import in his poetics.