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Given this background, it is surprising that Wain developed into a talented artist. As a young man he supported his family through freelance illustration work, focusing on pastoral scenes. However, the field of freelancers was crowded, and Wain struggled to find prominence.
In 1883, he married Emily Richardson, but their happiness turned to tragedy when she became ill with cancer three years later. They found some comfort in the companionship of their much-loved pet cat, and Wain was inspired to make some cat drawings.
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After a stint in New York City doing a cat-themed comic-strip for the loathsome William Randolph Heart, Wain found himself broke and unable to sustain the whimsy of his previous work. He returned to London, where he learned that his mother had died in the 1918 flu pandemic. Unable to cope with his grief, Wain began to fray at the seams and his mental health declined. Accordingly, his cats no longer beamed with humor, and instead radiated paranoia and dread. Wain's relationship with his sisters deteriorated as he became obsessive, reclusive, and unstable.
By 1924, Wain had become violent and was committed to a mental institution. He spent the following years oscillating between calm lucidity and angry incoherence. The commonly accepted theory is that Wain had developed schizophrenia, but in lieu of a proper diagnosis it is impossible to tell what had happened to the poor man. When word spread that the once-famous illustrator was languishing in a drab hospital room, there was outrage amongst his fans and admirers, including such influential figures as the legendary science-fiction writer H.G. Wells.
At the behest of Wells and others, Wain was transferred to a far more a comfortable mental hospital. While Wain never recovered from his illness, the change of environment had a pronounced effect on him and his mood swings ended. Instead, he lived in quiet dementia, tending to a garden and caring for several pet cats that the hospital allowed him to keep. He also returned to art and produced many new beautiful illustrations. The pieces that he produced at the end of his life were highly abstract, and dazzlingly elaborate, and yet the familiar face of a cat is instantly recognizable.
Wain died on July 4th, 1939. His work is highly collectible, especially amongst both cat fanciers and psychology enthusiasts.