The son of Kent Telfer Damon, a stockbroker, realtor, and tax preparer, and Nancy Carlsson-Paige, an early childhood education professor at Lesley University, Damon attended Cambridge Rindge and Latin School in Cambridge, and performed in several theater productions. He graduated from the school in 1988 and began attending Harvard University the same year. Here he studied English and lived in Lowell House. He could have graduated in 1992, but chose to defer classes to pursue acting projects.