Charles Hopkinson was born in 1869, in Cambridge, Massachusetts. After graduating from Harvard he began his formal artistic training at the Art Students’ League in New York. While at the ASL, he studied cast drawing under Twachtman and the figure under Mowbray.
In 1893, with his first wife, Angelica Rathbone, he moved to Paris. Angelica was an aspiring artist as well and both enrolled at the Atelier Julien. Bouguereau was their teacher.
Due to his long history with Boston’s elite and the sheer number of portraits he painted of Harvard alumni, he has been called the Court Painter of Harvard. In 1948, Time Magazine called him The Dean of U.S. Portraitists.
He returned to Europe in 1901, where he visited Spain to study the painting of Velázquez and El Greco and traveled through Brittany, and the Netherlands to see portraits by his "heroes", Frans Hals and Rembrandt.
Hopkinson then began a lucrative career as a portrait painter in Cambridge winning awards like the Logan Medal of the arts (1926), and soon his first commission being a baby portrait in 1896 of poet E. E. Cummings, a work that is in the Massachusetts Historical Society. Adopting the colour theories of his former neighbour Denman Ross, who had become a prominent collector and a teacher at Harvard, Hopkinson later used the results of Carl Cutler's experiments with a spinning disk to study the color spectrum. He exhibited regularly in the national annuals and at several Boston and New York galleries. His watercolors were described as "modern" in the press and he exhibited three oils in the 1913 Armory Show. Instead of allying himself with the local established painters, Hopkinson showed his work with the "Boston Five", a group of young watercolorists though he continued to paint in oil for an elite clientele. In 1919 the National Art Commission selected him to paint some of the participants of the Peace Conference at Versailles, France. In 1927 he was elected into the National Academy of Design as an Associate member and became a full Academician in 1929. In the mid-1920s, Hopkinson took on a young Boston painter Pietro Pezzati as his assistant, who worked with him at his Fenway studio. Hopkinson would pass on his studio to Pezzati when he died in October 1962, in Beverly, Massachusetts.