A graduate of Cowell College of the University of California, Santa Cruz (1974), Weschler was for over twenty years (1981–2002) a staff writer at The New Yorker, where his work shuttled between political tragedies and cultural comedies. He is a two-time winner of the George Polk Awards—for Cultural Reporting in 1988 and Magazine Reporting in 1992—and was also a recipient of the Lannan Literary Award (1998).