At age sixteen Samuel Lovett Waldo convinced his parents to allow him to attend drawing classes in Hartford. After an unsuccessful attempt at establishing his name as a portraitist he moved to Charleston, South Carolina. There he met with better fortune and by 1806 had saved enough money to allow him to travel to England. In England Waldo enrolled in the schools of the Royal Academy and soon came to the attention of the expatriate American artist, and president of the Royal Academy, Benjamin West (q.v.). Although Waldo did not establish a strong reputation in London, he received enough commissions to allow him to pursue his studies until 1809 when he decided to return to the United States.
Upon his return Waldo settled in New York City and soon established a modest reputation for his portraits. In 1817 Waldo became a member of the American Academy of Fine Arts and was immediately elected to its board of directors. Two years later he executed his painting Old Pat, the Independent Beggar (Boston Athenaeum) that established his name as an innovative painter. In 1820 he entered a partnership with his friend and former student William Jewett (q.v.), and the two continued to work together for the remainder of Waldo's life. When the National Academy of Design was founded in 1826, Waldo was immediately elected to its body. Despite the honor, Waldo chose to retain his ties to the American Academy of Fine Arts, and there is no evidence that he played an active role in the Academy during its early years. From 1829 to 1835 he served as vice president of the American Academy.
After the American Academy failed, Waldo and Jewett renewed their interest in the National Academy and their portraits were frequently included in its annual exhibitions. They continued to prosper and during the 1840s and 1850s were commissioned to execute portraits of many of New York's leading citizens.
