Around 1875, John Singer Sargent painted a small oil picture of two octopuses on the deck of a fishing boat near Brittany. This canvas, now titled Two Octopi , is one of the very earliest oil paintings in the artist's oeuvre and shows Sargent's youthful proficiency in the medium. Even more remarkable is Sargent's peculiar choice of subject, particularly for an artist who would become famous for his portraits of high society. This essay examines the different evidence one can mine from Two Octopi: Sargent's early travels, academic training, and visual and tactile imagination. It also draws on culinary history of the notorious “devil fish” to demonstrate the uninhibited ambitions and adventurous choices of a young artist on the brink of his professional career.