Winston Churchill produced over 550 paintings throughout his life

In 1920s articles that would eventually become the tiny book "Painting as a Pastime", Churchill would later write, "Painting came to my rescue in a very difficult time." The renowned British politician turned to his pastime as a source of enjoyment and a break from the pressures of his job. Over 550 paintings would ultimately be produced by him, and he attributed the work to sharpening his visual perception, observational skills, and memory. As he advanced in his career as a renowned author, orator, and political figure, the hobby would blossom and might even help him.

Some have attempted to establish a distinction between Churchill's artistic endeavors and his renowned literary prowess. According to Timothy Riley, director and principal curator of the National Churchill Museum in Missouri, "How he picked up a paintbrush is akin to how he picked up a pen to write a speech. His artwork originates from the same location. He was inspired as a politician, writer, reader, and painter by his great mind, vision, and ability of observation." And Sandys also thinks that Churchill was a better leader as a result of his hobby of painting, particularly since it helped him become a better observer and remember. He cited the Battle of Britain in 1940, which occurred soon after Churchill was appointed prime minister and during which he visited the front lines to see firsthand how the British defended itself. Sandys said, observing that it may have enabled him to assess the whole image of the battlefield and recognize the areas for improvement, "Perhaps he felt that by going down there and looking at these things firsthand, he would see more and recall it more precisely." The painting was a contributing element to some of the choices he made at that crucial time.

However, his method of painting was very different from his method of writing. While he struggled with painting, he was naturally gifted at writing, which he relied on for his livelihood for most of his life. "With painting, Churchill was forever the keen student, whereas, with words, he was always the master," according to Carter. Churchill believed that formal art instruction was a young person's game and was mostly self-taught. He thought that a certain type of enthusiasm was what he and his like-minded amateur colleagues most required. Nevertheless, he was eager to hone his skills and did so by picking up tips from notable performers, he befriended painter Paul Maze. For the remainder of their lives, the two remained close friends and painting partners. Most of Churchill's surviving paintings may be seen at Chartwell House in London, where he worked under the alias "Charles Morin."