Charles Noël Flagg was born on Christmas Day to the Reverend Jared Bradley Flagg and his second wife, Louisa Hart. He was a descendant of the painter Washington Allston. His first art teacher was his father, who in 1863 had given up the ministry in favor of a career as a portraitist, moving his family to New Haven. The younger Flagg tried his hand at portraiture as early as age thirteen. He was seventeen when he began working seriously and twenty when he established his own studio in Hartford. In 1872, accompanied by his half-brother Montague and the artists Robert B. Brandegee and William Faxon, Flagg went to Paris. There he studied with Louis-Marie-François Jacquesson de la Chevreuse, who had been a pupil of Jean-Auguste-Dominique Ingres. He returned to America in 1874 but went back to Paris in 1877, this time staying five years.
Returning in 1882, Flagg settled in Eastchester, New York. He also shared a studio with Montague in New York, where they taught drawing. Flagg passed the summer and autumn of 1885 in Minneapolis and Saint Paul, painting portraits. Among the prominent people who were his sitters were Minnesota governor Lucius Frederick Hubbard and his wife. An exhibition of his work held at the close of this stay was outstandingly successful, and he returned to Saint Paul for the 1886 and 1887 seasons.
In 1887 Flagg moved permanently to Hartford, becoming the leading portrait painter of the area. His sitters included most of Connecticut's late-nineteenth-century governors, other state officials, and Hartford's civic and social leaders and celebrities, such as Mark Twain (1890, Metropolitan Museum of Art, New York).
In December 1888 Flagg was appointed an instructor of the Academy school's daytime antique class. Whether he fulfilled this engagement is not clear, because in the same year he established the Flagg Night School for Men in Hartford. Initially instruction was free, but as the student body grew-forcing Flagg to move to an adjacent studio to pursue his own work-voluntary fees were introduced to cover expenses. It was one of the nation's first cooperative art schools. In 1895 Flagg's school was incorporated as the Connecticut League of Art Students; he remained its chief instructor for the rest of his life. He also was a founder, in 1892, and first secretary of the Society of Hartford Artists. When that organization became the Connecticut Academy of Fine Arts in 1910, Flagg was elected its first president. He was active in many projects affecting the cultural life of Hartford, including, as first president of the city's Municipal Arts Society, the successful effort to prevent the state capitol from being demolished.
Four landscapes that Flagg submitted for an Academy annual when he was sixteen years old were rejected. He made his Academy debut in 1872 with a portrait of Montague Flagg. Thereafter he was frequently represented in annuals until the end of his life. His portrait of Paul Bartlett received the Thomas R. Proctor Prize in the winter exhibition of 1908, an occasion that seemed to have led to his election to the Academy.
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