Ichabod Crane c. 1937 Norman Rockwell (1894-1978) Oil on canvas In 1936, book publisher George Macy commissioned Norman Rockwell to illustrate new editions of Tom Sawyer and Huckleberry Finn. Eager to repeat Rockwell's success with additional titles, Macy encouraged him to explore other subjects for illustrated books. Rockwell began work on a series of pictures of celebrated characters in American fiction, which would be paired with excerpts from the stories. As one of the first in the series, he chose Ichabod Crane, the schoolmaster from the 1819 Washington Irving story The Legend of Sleepy Hollow. Rockwell painted this first version of Ichabod and then a second, more developed version, which is now in the collection of Utah's Draper Elementary School.
It is likely that Rockwell's good friend and New Rochelle model Fred Hildebrandt, who had just posed as the schoolmaster in Tom Sawyer, also appears in Ichabod Crane. Irving described his character as "tall, but exceedingly lank, with narrow shoulders, long arms and legs, hands that dangled a mile out of his sleeves, feet that might have served for shovels, and his whole frame most loosely hung together. His head was small, and flat at top, with huge ears, large green glassy eyes, and a long snipe nose, so that it looked like a weathercock perched upon his spindle neck to tell which way the wind blew."
Rockwell's artistic interpretation departs from a version created ten years earlier by Arthur Rackham, one of his favorite illustrators. Rackham's spidery pen-and-ink rendering suits the skinny, gawky Crane, whereas Rockwell's figure is more substantial, making us feel slightly unsettled by the penetrating demeanor of his sideways glance, and fortunate that we are confronted by a painting and not the actual man. Unpublished illustration 49.5 x 24.5 inches Norman Rockwell Art Collection Trust, NRACT.1973.107 Licensed by Norman Rockwell Licensing Company, Niles, IL.