Best. Movies. Ever.

They may be the two most terrifying words in publishing: Anna Wintour. Those dark glasses, that scowl, the fur coats that protect her like armor—even Meryl Streep was afraid to caricature her too much in The Devil Wears Prada. So it's surprising that in the new documentary The September Issue, which chronicles Vogue's biggest month of the year, Wintour comes off as so likable. She's hardworking, diligent, nurturing—the kind of boss you'd actually want, even if she didn't wear Prada. Credit this fresh portrayal to R. J. Cutler, the film's director and a documentary veteran (The War Room, American High). We wondered: if he likes Wintour, what else does he like?

The perfect Hollywood story structure: Wall Street

The finest example of political cinema: On the Waterfront

My very favorite Woody Allen film: Crimes and Misdemeanors

Screwball comedy's top achievement: The Lady Eve

A movie that is the best biopic I've ever seen: All That Jazz

A movie that shows how love and crime are the same thing: Badlands

The movie that made me want to make documentary films: Harlan County U.S.A.

The movie I watched every day for three weeks when I was 13: Dog Day Afternoon