Wallace quickly immersed herself in modernist artists’ circles following her move to New York City around 1912. Her address books, which list popular social spots and now-famous names like Gertrude Whitney (1875-1942), Juliana Force (1876-1948), John Sloan (1871-1951), and Walter Arensberg (1878-1954), elicit images of spirited conversations held in dark bars and parties crowded into glittering rooms. Although we do not know the subject of this portrait, Wallace often painted her artistic friends, frequently representing them with the requisite cigarette in hand.