Crewdson was born in the Park Slope neighborhood of Brooklyn, NY. He attended John Dewey High School, graduating early.
As a teenager, he 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 Photo” 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, near Port Chester, NY. 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. He is now a professor at the Yale University School of Art. In 2012, he was the subject of the feature documentary film Gregory Crewdson: Brief Encounters.