In 1886, a nineteen-year-old artist, portfolio in hand, was seen sneaking his way up the back stairs to the New York City offices of the young humor magazine, LIFE. A tall, handsome youth, he hardly looked like the type that needed to sneak his way around anywhere. But he'd spent the entire year making the rounds of every magazine in New York and their unanimous rejection of his work had chipped away at his self-confidence. He had decided that this was it if LIFE didn't buy something, there would be one less artist struggling to sell his work.

Among the drawings in the portfolio was a sketch of a dog baying at the moon, with the legend beneath, "The Moon and I." It was a spoof on the ballad of the same...