Thomas De Witt was born in Kingston, New York, into a Dutch family of long ancestry in New York. A doctor of divinity, De Witt became one of the pastors of the Collegiate Dutch Reformed Church in New York City in 1827. He joined The New-York Historical Society in 1838, and two years later was elected a vice-president, an office he was to hold for nearly 30 years; he also served as the thirteenth president of the Society (1869-71).

The subject was born in Poughkeepsie, New York, the son of Henry Livingston and the great-grandson of Robert, first lord of Livingston Manor. He received his D.D. degree from the University of Utrecht in Holland in 1770 and became the minister of the Collegiate Reformed Church in New York. Dr. Livingston was a founder and president of Queen's College (now Rutgers). His portrait was a gift to the Society from his great-grandson.

Catharine De Peyster was the daughter of Abraham De Peyster, treasurer of New York from 1721 to 1767, and Margareta (Van Cortlandt) De Peyster. She married John Livingston in 1742. Her portrait was a gift to the Society from her great-granddaughter.

The subject was the father of Robert Livingston, the first lord of Livingston Manor on the banks of the Hudson River. He lived with his family in Rotterdam at the time this portrait was painted. The portrait may have been brought to America by his son Robert, who settled in the colonies in 1673.

Alexander Anderson was granted a license to practice medicine in 1795 and received his medical degree from Columbia College in 1796. When the yellow fever epidemic of 1798 struck, he lost not only his mother, father, and older brother, but also his young wife and infant son, as well as several members of his wife's family. After a journey to the West Indies he returned to New York, where by 1800 he settled down and devoted himself to the art of engraving. Anderson is considered the father of wood engraving in America.

The dress and mantle of this portrait are not finished. Since it was never finished, it may have been painted for Vanderlyn himself, who considered Mrs. Burr to be a dear friend.

This portrait was a companion to the 1802 portrait of Burr himself.

The Pocahontas theme and Indian subjects illustrating the colonization of Virginia were favorites of Chapman. In 1836 he exhibited his "Coronation of Powhatan" and "The Warning of Pocahontas" and in 1837 "The First Ship" at the National Academy of Design. In the latter year he was awarded the commission for a mural of the baptism of Pocahontas; it was installed in the rotunda of the Capitol in 1840. His "Landing at Jamestown," engraved by M. I. Danforth, was published in the New-York Mirror on October 19, 1839. These works suggest possible dates of execution of the Society's study. The incident depicted allegedly occurred in 1608 after the capture of Captain John Smith of the Virginia colony by Powhatan's Indians. According to Smith's statement in his Generall Historie of Virginia, printed in 1624, he would have been killed had it not been for the intervention of Powhatan's young daughter, Pocahontas (ca. 1595-1617), who laid her head on his own to save him from being clubbed to death.

Painting depicts the naval engagement between the U.S. Frigate Constitution and H.M.S. Gurrier in 1812. Once her mizzen mast was down, things only got worse for the British frigate Guerriere, 38 guns, in her battle with the U.S. frigate Constitution, 44 guns, near the Grand Banks. It was the first of the frigate duels in the War of 1812, and given the losses the U.S. had sustained on land in that year, a great booster of morale. Chapman fills the sky with clouds and shows the Guerriere, utterly helpless, after her mainmast and foremast had also collapsed. The captain of the Constitution, Isaac Hull, made his fame on that night.