John Singer Sargent remains unchallenged as the finest, flashiest portrait painter of his era. He was lionized during his career, and the purchase of his work by the National Gallery in London earned him the encomium "the only living old master." Famous for his bravura brushwork, able to transform a daub of white pigment into a sparkling diamond ring, Sargent also displayed an astonishing grasp of psychological nuance that turned his likenesses of the fashionable world into a sophisticated mirror of his times.

Sargent's national identity has been debated, for he was truly expatriate and cosmopolitan. Born in Florence to American parents, he was brought up and educated in Rome, Nice, and Germany. At eighteen, he began his study of art in Paris at the studio of Carolus-Duran and gained recognition five years later when he exhibited a portrait of his teacher in the Salon of 1879. In 1879, Sargent made his first journey to Spain and Morocco, where he discovered the dark, moody manner of Velazquez and Goya, which would dramatically affect his own style.

By the time Sargent made his first trip to America in 1887-88, he had settled permanently in London and had achieved international success. In America, he was deluged with portrait commissions. On a visit to New York in 1890, the painter and his sister Violet attended a party at the famous Tenth Street studio of William Merritt Chase. There he encountered his friend the sculptor Augustus Saint-Gaudens, who wanted to make a bas-relief of Violet's beautiful Grecian profile. In return Sargent agreed to do a portrait of the sculptor's ten-year-old son Homer (1880-1958), which he executed in his New York studio that year.

Homer hated sitting for the portrait. Posed against a dark background evocative of Velazquez, he squirmed restlessly on a straight-backed chair, dressed in an uncomfortable black velvet Fauntleroy suit. The boy's mother, a cousin of Winslow Homer, is also in the portrait, and he had to endure her constant rereading of the account of the battle between the Constitution and the Guerrière. Furthermore, Homer disliked Sargent, who, he said, "squelched the small boy's obstreperousness every few minutes by just plain sitting on him." Though Homer suffered, it took only seven sittings to complete the canvas, a short time for a work of this size which is really a double portrait.

Fluidly brushed, the picture is a technical tour de force as well as a striking example, in its faithful echo of the child's petulant resignation, of the artist's sensitivity to psychological realism. In this regard, it is worth noting that Sargent's depiction of American children differs markedly from the way in which he showed young Europeans. His portraits contrast the rambunctious youth of the New World with the demure, courtly, and somewhat blasé attitudes of their Old World counterparts.

Homer Saint-Gaudens grew up to attend Harvard, write short stories, and work for fourteen years as stage manager to the actress Maude Adams. In 1923 he became director of the department of fine arts of Carnegie Institute, a position he held until 1950.