The 10 Best Woody Allen Movies

Forty-four features over 48 years. That’s a lot of cinema to emerge from the mind of one man, however tireless and prolific. Woody Allen’s approach to filmmaking shares more in common with the routine, unfussy diligence of the classical studio era than modern auteurism, which is to say that Allen treats his vocation less like a tortuous calling than, well, a job, something to sit down and do every day. His latest feature, Magic in the Moonlight, arrives in theaters this week, maintaining a release streak that has brought us nearly a film a year for going on five decades. Allen has a reputation for discarding each film as it passes him by, not bothering to reflect on their importance or worry about their legacies; his attentions are drawn to what’s next so quickly that he hardly has time to bother with his own history. It’s safe to say that Allen wouldn’t have much time for a list such as this. Still, the canon cries out for rejuvenation, and so we size up another annual Allen tradition: the commemoration of his greatest hits.

10. Manhattan Murder Mystery (1993)

Considerably (and refreshingly) breezier than the melodrama mined by his previous feature, Husbands and Wives, the jubilant comic-thriller Manhattan Murder Mystery is perhaps Allen’s best “minor” film—a more notable distinction than it sounds. Expanded from material originally developed as a framework for Annie Hall, it retains much of the manic wit and inventiveness of its spiritual predecessor, making it an effortless hit in a decade littered with misses.

9. Bananas (1971)

Allen rather famously complained, in 1981’s limply satirical Stardust Memories, that audiences invariably preferred his “earlier, funnier films” to the more serious artistic efforts he’d since graduated to, but it’s not hard to sympathize with the preferences of the hoi polloi. At a scant 82 minutes, Bananas is loose and sketch-like, flitting from one roaringly funny comic set piece to another with little regard for cogency. It hardly matters, as the film is so wildly funny scene for scene that the gags themselves qualify as substance.

8. Crimes and Misdemeanors (1989)

Life as tragedy, life as farce: Crimes and Misdemeanors describes both arcs and, in keeping with Allen’s existentialist bent, switches the endings. Martin Landau, the tragic figure, snuffs out an innocent life, only to walk away unpunished and without remorse; meanwhile Allen, the ever-hapless comic hero, finds his noble life rewarded with punishment, his mentor dead and his beau running off with swine. It’s Allen’s bleakest film, of course—pitch-black and unforgiving. But in the intensity of its hopelessness it ranks among his wisest.

7. Sleeper (1973)

The sort of high-concept comedy Allen would abandon by the late 1970s, Sleeper is, plainly, a master class in comic riffing. Allen plays Miles Monroe, another take on his trademark nebbish, who finds himself cryofrozen in 1973 only to wake up 200 years hence. The comedy comes not, as you might expect, from the fish-out-of-water’s stunned reactions to the advancements of the future, but rather to the future-world’s bafflement over this curious Manhattanite dweeb. It’s a brilliant twist, replete with genre-upturning lunacy and moments of inspired bathos.

6. The Purple Rose of Cairo (1985)

A nostalgist’s weakness for “the magic of the movies” threatens to make this all little more than a meekly wistful ode to the medium’s golden age, but Allen proves too smart to let the impulse get the better of him. Instead, The Purple Rose of Cairo is a swooning paeon laced with bitterness and regret, a reality check driven home by the film’s brilliantly unhappy ending. The movies, it seems to say, are indeed an escape—but only for 90 minutes.

5. 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?

4. 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.

3. 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.

2. 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.

1. 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.