When he was a teenager he moved with his family to Chicago. There he attended the Chicago Art Institute, graduating in 1956. Estes says that he tried to paint like that but did not enjoy it. After graduation he worked as a commercial artist doing things like advertisements and signs. Estes is often called a pioneer of the photo-realism style.
Photo realists are people who paint photo images.
Estes takes pictures primarily on the streets of New York City where he lives, although he has also worked in Venice, Chicago, and Paris. He takes them on Sundays when the streets are quiet and empty. In the studio, he usually works from more than one photograph to compose a painting. He draws the scenes freehand, rather than using a grid or tracing. Estes has said that he would not be able to paint a photograph of a place that he had not visited himself.