In 1783, he produced a portrait of George Washington, now owned by the United States Senate, and later studied art under Benjamin West in London. Another teacher was Abraham Delanoy, with whom he had a handful of lessons in New New York
He was a producer, playwright, and actor, as well as a historian. He managed two of New York"s earliest and most prominent theaters, the John Street Theatre (from 1796-1798) and the Park Theatre (from 1798–1805). He was also an artist, despite losing an eye in childhood.
After returning to America in 1787, he worked exclusively in the theater for 18 years, resuming painting out of economic necessity in 1805.
By 1817, he was a full-time painter. In his lifetime he produced more than sixty plays, most of which were adaptations or translations from French or German works.
A few were original: these were based on American themes and had American characters. However, he is best known for his encyclopedic three-volume History of the Rise and Progress of the Arts of Design in the United States, which was published in 1834, and which is now an invaluable source of information about artists, collecting, and artistic life generally in the colonial and federal periods.
Among his plays were the following:
The Father (1789)
The Stranger (1798)
The Italian Father (1799)
False Shame (1799)
The Virgin of the Sun (1800)
Memoirs of George Frederick Cooke (1813)
A Trip to Niagara (1828)
History of the American Theater, 2 volumes
In 1825 Dunlap was one of the founders of the National Academy of Design, and taught at its school.