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.

Street had six children by three wives, at least four of whom became artists. He died in Philadelphia in 1865.