Crewdson was born in Park Slope, a neighborhood in Brooklyn. As a teenager was part of a punk rock group called The Speedies that hit the New York scene in selling out shows all over town. Their hit song "Let Me Take Your Foto" proved to be prophetic to what Crewdson would become later in life. In 2005, Hewlett Packard used the song in advertisements to promote its digital cameras.
In the mid 1980s Crewdson studied photography at SUNY Purchase. He received his Master of Fine Arts from Yale University. He has taught at Sarah Lawrence, Cooper Union, Vassar College and Yale University where he has been on the faculty since 1993.
Crewdson is represented in New York at the Luhring Augustine Gallery and in London by the White Cube Galler