Humphrey's interest in art began at age four when he had his own portrait painted by his aunt. His skills and interest grew quickly, and a long trip to Europe, in 1929, allowed him to see all the famous works of the Byzantine period, the German Expressionists, the Italian Renaissance paintings, and the works of Van Gogh.

His interests did not stop with art, however. He was a violinist and played in the local symphony orchestra for seven years. He also wished to write among other things. His main love was painting, though, and he experimented with many types of paint and materials such as oils, charcoal, chalk, pastels, pencil, watercolours, and acrylic. He painted on canvas, wood, masonite, or any other substance which could add character to his abstract art. Upon his return from Paris, he was inspired with many ideas for abstract work. While he was also known as a 'magic realist', his abstract work was exceptional. His works included portraits and still-lifes.

By 1935, he had achieved national recognition, and in 1951, he received an honourary degree of Doctor of Laws which was very rare for a Canadian artist at that time. He was a member of the Eastern Group of Painters as well as the Canadian Society of Painters in Watercolour which he joined in 1939. He belonged to the Canadian Group of Painters, formerly the Group of Seven, as well.

Humphrey was often called a regionalist, but this was mistakenly said. He was not a regionalist for its own sake. He merely felt more at home and more inspired by his home region.

Donald Buchanan said of Jack Humphrey

In his quarters, Humphrey from time to time entertains his friends...occasionally there will be a magnificent meal...Sometimes he will play the violin to the accompaniment of a grand or upright 'box' piano...there will be plenty of talk and argument, but little from Humphrey. He prefers mostly to sit with his impressive bulk slumped in a chair, his contemplative blue eyes sunk beneath his high forehead with its wisps of grizzled hair, and about his lips a half-smile as if enjoying some inner joke...He does not talk much about his painting; he prefers to listen, and to paint; he remains aloof, monolithic and introvert.

Humphrey's work can be found in the National Gallery of Canada, University of Toronto, Art Gallery of Ontario, and many other galleries across Canada.

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