John Wesley Dennis was born on May 16, 1903 in Davisville, Massachusetts. His father, John W. Dennis, was born in
England and educated in Cambridge. He came to the United States with his track team for an international sports event.
While here, he met Miss Ida Morgan, a tearoom waitress. After they were married, John get a job in the composing room of
The Boston Globe.
Wesley wrote that the first horse he can remember was the family horse he used to hitch to the cart to go to the train station and pick up his father, who only came home to Cape Cod on the weekends. The horse was called Tony. After Tony died, Wesley acquired a “bobtailed, high-stepping saddle horse” from a woman for whom his mother made dresses. Since his father would only let him keep “Bob” if could be useful in some way, Wesley got him to wear a harness to help cultivate turnips. He would also ride Bob bareback to and from school.
Although his mother had hopes he would become postmaster, he dropped out of high school at age 17 after failing the entrance exam for the Naval Academy in Annapolis. He moved to Boston where his older brother Morgan was working as an artist for the Boston Herald. He initially lived with Morgan and got his first job at the Boston American by using his brother’s sketches! While in Boston, he also attended the New School of Design. Over those ten years, he did fashion advertising sketches for the newspapers for department stores, such as Filene’s and Jordan Marsh Company. Although it provided a steady income, he later described those years as “the most boring years of my life, and when it comes time to die I hope God won’t count them.” Newspaper ads for Filene’s at one point advertised “Personalized Christmas cards designed for you by Mr. J. Wesley Dennis.” Fifty cards cost $10.
His brother Morgan eventually made a career etching and painting dogs. Wesley was more interested in horses. He eventually joined the Massachusetts National Guard Cavalry so he could have access to horses without the expense. He was very interested in playing polo and found that he could purchase a couple polo ponies and keep them at the Commonwealth Armory at the expense of the government - as long as they could be used in an emergency. He requested (and was granted) the job of grooming the horses at Camp Devins. “It is one of the best ways to learn the shape of a horse,” he said. Wesley also made extra money by doing charcoal sketches of the officers, charging them according to rank.
Somewhere around this time, Wesley met and married Mrs. Olive Garland. She was a widow living in Buzzards Bay. The Garlands had a ranch in Santa Fe, New Mexico. The bleached skeletons of horses provided him with good anatomy lessons. They divorced, but Wesley remained a friend of the family. He was renting a studio in Buzzards Bay from his stepson at the time of his death.
Wesley eventually wrote to the animal and landscape artist Lowes Dalbiac Luard, who lived in Paris, asking him to be his teacher. Mr. Luard replied that he did not take students but would help in any way he could. With that response, Wesley left for France. Mr Luard stressed the importance of memory. Wesley said that he would set out a cup and saucer, only for a minute, then take it away, and ask that it be drawn from memory. The ability to clearly remember distinct images served Wesley well in his illustrations. Mr. Luard also took him to butcher shops to study the musculature and anatomy of horses. Wesley returned from France in 1932.
After returning, he spent a lot of time at racetracks, sketching horses, and if he was lucky, selling the sketches to the owners of winning horses. He also did some work for newspapers such as The Boston Globe. One of his early breaks was a commission from Esquire magazine to paint a series of famous horses from various breeds. He also sent a portfolio of horse portraits to Bing Crosby after hearing he liked horses. He hoped Mr. Crosby would buy one, and to Wesley’s surprise, he bought all of them.
In the late 1930s, while playing polo at Coonamessett on Cape Cod, he met Miss Dorothy Schiller Boggs. They married. While on their honeymoon in Santa Fe, New Mexico, he met May Massey, juvenile editor for Viking Press. He asked her if she knew of any work illustrating children’s books. Ms. Massey did not, but she suggested he write and illustrate his own book, leading to the creation of Flip, which was published in 1941.
References available upon request.