His first ambition was to have a career in music for which he claims he started a career as a violinist. He abandoned this in his mid-teens and signed up for the West London School of Art in 1877. There he studied until 1880 and then stayed on for a further three years as a teacher. Wain returned home after his father died to support his mother and sisters. He began working as a freelance artist, painting commissioned portraits for country estates and livestock shows.
At 23, he married his sister's governess, Emily Richardson, (scandalously 10 years his senior) and moved with her to north London. Shortly after getting married, Emily was diagnosed with breast cancer and passed away 3 years later. During the years of her illness, Wain engaged Emily's cat Peter to amuse her by dressing him up in clothing and spectacles, and teaching him tricks, all the while creating sketches.
At the time, there was little demand for cat illustrations and his drawings were kept for private use only. Cats were held in low esteem at the time.
In 1886, Wain was asked by Macmillans to illustrate a children's book entitled 'Madame Tabby's Establishment'. The results proved popular and encouraged Illustrated Sporting and Dramatic News, where Wain worked, to produce a double page cat drawing for the Christmas Issue. The result was 'A Kitten's Christmas Party' containing over 150 cats and almost overnight, Wain became one of the most popular illustrators of the day.
Wain is best known for his anthropomorphic large-eyed cats and kittens. As time passed, Wain's cats became increasingly human in their behaviour and appearance. The year 1890 was when his cats began to walk on their hind legs, don fancy neckwear, and sport monacles and walking sticks. They became more and more uncatlike and more like naughty children.
A victim of schizophrenia, he spent the final 15 years of his life in a comfortable asylum - drawing cats.