Cowpie had attended the Hudson River School of Art in the upper Bronx, which turned out some of America's finest landscape painters, but, as Cowpie has said in his autobiography, "we didn't have much call to do faces and such, mostly trees, rocks, rivers, you know, that sort of thing."

However, with the colonial landscape market saturated, portraiture was the money was, and Cowpie did his best to cash in on the trend. His uncompleted outdoor portraits show the typical Hudson River School alumni's grasp of landscape detail, and he was able to apply his skills admirably to the textures of clothing. But facial features continued to elude him. "I stank at noses," he recalled, "they always wound up looking like baby sweet potatoes or peach blossoms, only not so well-executed. And dogs and horses, don't even talk to me about dogs and horses." 

Cowpie eventually found a landscape-painting job as the frontier moved westward, and later in life founded the Missouri River School of Art.

 

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