At Purchase College, State University of New York, he began experimenting with photography, not yet taking it seriously, Crewdson only saw it as a creative outlet and hobby. Gaining school recognition and a growing interest for art, he graduated undergraduate from SUNY Purchase and later attended Yale University receiving his Master of Fine Arts. His senior thesis embodied everyday life through portraiture of Lee, Massachusetts residents, the same location that later inspired his first series "Natural Wonder" from 1992 to 1997. 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 . The film series followed the construction and the behind-the-scenes explanation from Crewdson himself of his thought process and vision for his pieces of his collection "Beneath the Roses".