Sloan began painting The Wake of the Ferry II in 1907, his second version of this scene. The subject may well have been suggested by Sloan’s ferry trips with his wife from Jersey City to Philadelphia for medical treatments.
The stylistic influence of Robert Henri, so pervasive in Sloan's early work, is apparent here; the scene has been broadly conceived, spontaneously conveyed, and boldly brushed, in a limited palette of grays and near-blacks. The composition reinforces the mood; the ferry's tilted angle, framing a view of the rough waters, is arresting, and the diagonal of the wake receding into the mist reinforces the sense of loneliness and distance. In this setting, the small figure on the right, understated and half lost in shadow, becomes the essential actor in this version of Sloan's human comedy and brings into focus its melancholy expression.
Writing in A Collection in the Making, Duncan Phillips admired Sloan's ability to evoke a specific mood. "Sloan, during that earlier New York period," he wrote, "was a splendid painter and space composer. He could take the ugly facts of a scene like the deck of a ferry boat on a rainy day and make his use of gray not only dramatic but infinitely subtle in its scale of 'values.'"
In 1971 The Wake of the Ferry II was selected by the United States Postal Service for a stamp commemorating the centennial year of Sloan's birth.