Born in Petersburg, Virginia and raised in Philadelphia, Trenton and Baltimore, he spent his adult life in New York City. He was an actor and scene painter, and studied art at Cooper Union and the Art Students League where his main teacher was George de Forest Brush. In 1896 and 1914, he was in Paris, but his main classroom was the streets of New York and the "raffish" side of society--immigrants in ghetto settings, market scenes, children playing, etc. Henri rejected his work for "The Eight" exhibit for being too soft and sentimental, but he helped organize and exhibited in the Armory Show of 1913. He won numerous prizes.