Hill had an artistically rich upbringing that was unusual for his time. His father took time to encourage his son in his artistic pursuits, and Jerome's grandfather's house, with its huge collection of paintings by European masters, was literally next-door.

Hill showed an early talent for painting. In a set of watercolors contained in the collection, completed at eight years of age, Hill's talents are obvious. He continued developing these skills throughout his childhood. Later in life, Hill asked his brother Louis Jr. to destroy many of his early drawings that were still stored at the house. The set of watercolors is one of the few childhood projects to survive. Another can be found at the Saint Paul Academy, where a set of murals Hill painted in a science classroom can still be seen. Hill created the murals, which portray events from the history of scientific discovery, while a student at the Academy. In 1964, he returned to touch up the paintings and to add a scene depicting Albert Einstein.

Immediately after graduating from Yale with a major in music, Hill sought to get back to painting. Making the most of his post-collegiate freedom, he traveled to Europe and studied at the British Academy of Painting in Rome and the Academie Scandinave in Paris. In addition to traditional painting subjects, Hill also enjoyed architectural drawing and traveled to many classical sites while in Europe.

In the mid 1930s, Hill began spending more time making films and less on painting. He did not return to painting in earnest until the 1950s, when he began to call Cassis his home for a majority of the year. Cassis offered him an opportunity to practice his landscape painting, and he utilized the bright palette of the French coast to great effect in his portraits and studies. The collection has reproductions of most of the paintings that Hill completed from 1960 to 1972.