Annie Hall

“I feel that life is divided into the horrible and the miserable.” One of the most compelling neurotics ever committed to celluloid, Woody Allen’s perpetual outsider Alvy Singer is a twice-married New York comic whose uneasy relationship with his titular WASP girlfriend (Keaton, in her fourth collaboration with Allen) is just one expression of a general uneasiness with life itself—or, as he might put it, with the dubious honor of belonging to a club that would have him as a member. 31-year-old Keaton collaborated with costume designer Ruth Morley to devise her character’s unassumingly sexy, casually gender-bending “look,” which would emerge as a cultural phenomenon unto itself; Keaton would go on to earn an Oscar for her winningly idiosyncratic performance. Borrowing liberally from Bergman and Fellini, Annie Hall pioneered a postmodern rom-com vernacular that would define the genre for decades to come, and cemented Keaton’s status as the endearingly flawed poster child for a generation of women newly coming into their own. “La-dee-da, la-dee-da.”