In 2007, Cutler spent seven months filming legendary Vogue editor Anna Wintour and her staff as they produced what was at the time the single largest single issue of a magazine that had ever been published: the September, 2007 Vogue, which weighed in at 840 pages and 4.1 pounds. The film that resulted was The September Issue, directed and produced by Cutler, and financed by A&E IndieFilms. While "The September Issue" features a host of Vogue personalities, designers, models, photographers, and others, its principal subject is the conflict-laden but deeply symbiotic relationship between the powerful, influential and notoriously frosty Wintour and her passionate fire-haired Creative Director Grace Coddington.