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Annie Hall (1977)

It’s the variety-hour ingenuity of Allen’s early comedies that gives Annie Hall its jazz-like vigor, whisking us from one flight of comic fancy to the next with abandon. It’s a romance as reverie, the ultimate postmodern love story, its reality always on the verge of collapsing into dreams: Where else will you find contemporary media theorists pulled in as intellectual pitch-hitters, or watch as an argument is interrupted by a cartoon?


Manhattan (1979)

For all its quintessential “Allenness” (the anxiety, the erudition, the in-jokes, and one-liners), many of Manhattan’s best qualities are in fact the contributions of Allen’s well-chosen collaborators and peers. This is something of a curatorial masterwork: the smoky chiaroscuro etched out by DP Gordon Willis, the celebratory boom drummed up by George Gershwin, and the combative intellectual bravado of Diane Keaton’s performance are hallmarks of a director whose work is invigorated by his own stellar taste.


Love and Death (1975)

Allen’s major transitional film heralded a shift in sensibility from the “early, funnier” works to the more serious dramatic comedies to follow, but Love and Death does more than simply split the difference between Sleeper and Annie Hall. For one thing, it’s funnier than both, mining its parodic high concept—an extended riff on the history of Russian literature—for all it’s worth (and then some). It’s also perhaps Allen’s most successful efforts to reconcile his overflowing intellectualism with the populist comic sensibility that made him a star.


Zelig (1983)

We are infinitely pliable. That’s the thesis of Zelig, Allen’s wisest film, which has much to say about the way a person can be bent and contorted in the name of acceptance. Its ostensibly wacky conceit—the film is presented as an archival documentary about a man capable of physically altering his appearance to be more like the people around him—is grounded in an emotional and psychological reality all too familiar to shrug off as farce. We’ll go very far out of our way to avoid conflict. Zelig seizes on that weakness and forces us to recognize it.


Hannah and Her Sisters (1986)

Allen’s greatest film strays little from the template he’s adopted dozens of times over the course of his nearly 50-year career, and on the surface, at least, there isn’t much to distinguish it from the rest: It’s still a dry, urbane comic-drama about romance in New York, gently shaken by anxiety and charged by bookish wit. And yet in nearly every respect (its dense, heady script, a balancing act of conflicting desires and feelings; its stellar ensemble cast, lead by Michael Caine at his most searching and sensitive; even its wall-to-wall exemplary soundtrack), Hannah and Her Sisters towers over the filmography. It’s not just the best Woody Allen movie. It’s the platonic ideal of one.