Robert Street was born in 1796 in Germantown, Pennsylvania, the grandson of an English immigrant who had mistakenly been disinherited. His activity as an artist is undocumented until 1815, when he exhibited a painting at the Pennsylvania Academy of the Fine Arts. He exhibited there sporadically until 1861. Between 1821 and 1823 he achieved a measure of success by exhibiting four large biblical and subject scenes (including The Infuriated Maniac Assaulting his Keeper) at a number of locations in Philadelphia, and several other American cities. In 1824 he exhibited three historical paintings in Washington, D.C., and painted a portrait of Andrew Jackson (Sedalia Public Library, Missouri). Later that year he ceased painting historical subjects and began to concentrate on portraiture.

In 1834 Dunlap erroneously reported that "Street of Philadelphia, aimed at historical composition and died in Washington city." After receiving a corrective letter from the artist, Dunlap published a notice in the New York Mirror (28 February 1835) and announced that Street was alive and "prosperously pursuing his art in Philadelphia." Street was an active member of the Artists' Fund Society. In 1840 he organized an exhibition of 172 of his own paintings, along with his personal collection of "old masters," that was held at the Artists' Fund Hall in Philadelphia. He also exhibited at the Apollo Association in New York, in 1838 and 1839, and at the Franklin Institute in Philadelphia, in 1847 and 1851. Street had six children by three wives, at least four of whom became artists. He died in Philadelphia in 1865.

Although Street was chiefly a portraitist, he also painted landscapes and still lifes. He excelled in the difficult task of posthumous portraiture. Street's style, which remained fairly constant throughout his long career, was characterized by its naive, linear quality, and tentative grasp of perspective and anatomical draftsmanship. Despite strong competition from more sophisticated portraitists such as Thomas Sully, John Neagle, Jacob Eichholtz, and James Reid Lambdin, he enjoyed liberal patronage in Philadelphia. [This is an edited version of the artist's biography published, or to be published, in the NGA Systematic Catalogue]