The best and worst Woody Allen movies

From nourishment to nebbishment (and all points in between), we rank the comedian-director’s 43 features

He’s made a movie a year for decades—and we can’t hide our broadest smiles when Woody Allen’s white credits pop up on a black screen and the jazz music kicks in. As for the romances, dramas and comedies that follow? We’ve got opinions. Take a trip through our countdown of Woody’s career: his ups, his downs, his essential masterpieces.

Written by Dave Calhoun, Cath Clarke, Tom Huddleston, Joshua Rothkopf and Keith Uhlich

43–31

Scoop (2006)

The worst of Woody’s European jaunts, this one didn’t even receive theatrical distribution in the country in which it’s set: Britain. Woody paired himself with Scarlett Johansson to play, respectively, a magician called the Great Splendini and a journalism student who goes on the trail of a killer. It’s not radical to call it his low point.—Dave Calhoun

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Whatever Works (2009)

Originally written in the early 1970s as a project for the mighty Zero Mostel, this misanthropic comedy was rooted out of the script drawer and retooled for Curb Your Enthusiasm’s Larry David. The results aren’t terrible—just not especially likable. The characters are fairly obnoxious, the script is largely joke-free, and the plot doesn’t go anywhere.—Tom Huddleston

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Cassandra’s Dream (2007)

The beginning of the 21st century was a hard time to be a Woody Allen fan. On a losing streak of London-set films, he crossed to the dark side with this thin drama starring Ewan McGregor and Colin Farrell as brothers who agree to do a hit for their uncle to get them out of a tough spot.—Cath Clarke

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Anything Else (2003)

Smack-dab in the middle of a halfhearted period for the Woodman, this shrill romantic comedy stumbles mainly in casting: As the manipulative, noncommittal Amanda, Christina Ricci never quite taps into humor. Meanwhile, Jason Biggs turns Allen’s stammering everynebbish into a bland carbon copy. It feels like an American Pie sequel without the pastry.—Joshua Rothkopf

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Hollywood Ending (2002)

In what feels more like a padded short story, the director-star plays a formerly great filmmaker reduced to overseeing TV ads. When he’s finally tapped for a big project, the guy suffers an instant, psychosomatic stroke of blindness—yet the show goes on. The movie-set slapstick is tired, as are Allen’s satirical jabs at moneyed showbiz types.—Joshua Rothkopf

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Match Point (2005)

It was meant to be Woody’s comeback. Instead, it set the tone for his inexplicable “London period” of avoidable films, with their toneless dialogue and uneven acting. It’s a sub-Highsmith thriller about ambition and deception among the upper classes, in which a tennis coach (Jonathan Rhys Meyers) wheedles his way into a rich family.—Cath Clarke

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Melinda and Melinda (2004)

Overly schematic, this was the one that had a bunch of brainy playwrights eating at Pastis, batting around a simple scenario, one of them shaping it as a comedy, the other as drama. As the fictional title character, intense Radha Mitchell can’t pull off half of the equation—and it’s hard to say if Winona Ryder, intended to star, would have done it any better.—Joshua Rothkopf

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The Curse of the Jade Scorpion (2001)

This ’40s-set screwball comedy came shortly before Woody departed to make films in Europe for several years. It features the director as an insurance investigator who’s unwittingly hypnotized to carry out jewel heists; audiences struggled with the aging Allen putting himself in romantic situations with Charlize Theron.—Dave Calhoun

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To Rome with Love (2012)

An extremely patchy patchwork of stories set in modern Rome, this film has tourist Woody meeting his Italian future son-in-law for the first time in the Italian capital. The high point is an opera singer whose talents only emerge in the shower—so he takes the entire cubicle onstage with him, to great acclaim.—Dave Calhoun

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A Midsummer Night’s Sex Comedy (1982)

A rare straightforward remake for Woody—unsurprisingly, of an Ingmar Bergman movie. Smiles of a Summer Night (1955) was one of the Swedish master’s jolliest, least angst-ridden films, and Woody follows suit with an enormously likable if totally lightweight comedy of romantic misunderstandings in a bucolic country setting.—Tom Huddleston

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September (1987)

It’s hard to pick another American director as consistently on fire as Allen was in the ’80s, yet this Bergmanesque domestic drama outfoxed him. Notoriously, he reshot it with a different cast, but the longueurs remained. Regardless, the presence of a majestically rude Elaine Stritch (R.I.P.) goes a long way. It remains Allen’s worst-performing film, but an intriguing one.—Joshua Rothkopf

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Shadows and Fog (1991)

One of Woody’s less successful experiments with genre. Shadows and Fog draws on his beloved German Expressionism to create a world of murky morals and shifting allegiances, steeped in Kafkaesque angst. The film is beautiful to look at, but the mismatched cast-—John Malkovich, Jodie Foster, Madonna—and uneven script leave the film feeling awkward and uneasy.—Tom Huddleston

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30–21

Everyone Says I Love You (1996)

A Woody Allen musical drawing on the Great American Songbook was always going to be a love-it-or-leave-it affair. Roger Ebert rated the giddy Venice-set lark as one of Woody’s best, while others detected a lack of sparks between the megastar cast, one that included Julia Roberts, Edward Norton and Drew Barrymore, among others. All in all, it feels more like a technical exercise than a heartfelt romance.—Tom Huddleston

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Small Time Crooks (2000)

Time to exercise those muscles of compartmentalization: Half of this lunkhead crime comedy aches with obviousness, especially the overfamiliar plot (digging a tunnel under a nearby bank). But the other half is killer: two magnificent female turns, one from Tracey Ullman as a nouveau riche social climber, the other from Elaine May, raising pitch-perfect dumbness to high art.—Joshua Rothkopf

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Midnight in Paris (2011)

In the film that earned Woody a late-career box-office hit, Owen Wilson vacations in Paris with his fiancée (Rachel McAdams) and her parents; over several nights, he accidentally travels back to the 1920s. It’s easily the best of Woody’s European travelogue comedies, and the fantasy element offers flashes of the director’s earlier boldness.—Dave Calhoun

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Celebrity (1998)

Hollywood stars trip over themselves to work with Woody Allen: Wall-to-wall A-listers are the reason to watch Celebrity. In one of the funniest scenes, Kenneth Branagh’s journalist has sex with an actor (Melanie Griffiths) and then immediately pitches her a script. But best is Leonardo DiCarpio as a hotel-trashing bad boy (and remember, this was in DiCaprio’s Pussy Posse days, before he went all eco-crunchy.)—Cath Clarke

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Bananas (1971)

While trying to impress a girl, Allen’s neurotic New Yorker Fielding Mellish gets embroiled in a South American revolution and unwittingly ends up as the leader of a banana republic. Among the many gems: the dizzying courtroom sequence with its gut-busting wordplay (“It’s a travesty of a mockery of a sham of a mockery of a travesty of two mockeries of a sham!”) and special appearance by J. Edgar Hoover.—Keith Uhlich

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Manhattan Murder Mystery (1993)

This self-conscious attempt to return to the tone of his “early, funny films” following a series of darker efforts succeeds in large part, thanks to a wonderful cast of regulars: Anjelica Huston, Alan Alda, Diane Keaton and the director himself. It’s a goofy, lightweight Hitchcockian thriller crammed with good gags and fun characters.—Tom Huddleston

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Alice (1990)

A loose remake of Federico Fellini’s Juliet of the Spirits (1965), Allen’s romantic fantasy provides an exceptional showcase for Mia Farrow as an upper-class New York housewife whose placid existence is upended after she’s put under hypnosis. A single-take sequence where she confesses her feelings for costar Joe Mantegna is a comic-acting master class.—Keith Uhlich

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What’s Up, Tiger Lily? (1966)

For his feature debut, Allen took a Japanese spy film (Key of Keys) and overdubbed all the dialogue so that it become a comedy about the search for the world’s greatest egg-salad recipe. It’s a bit choppy at times, but the wordplay and sight gags—like the half-naked woman asking her lover to “name three presidents”—are consistently hilarious.—Keith Uhlich

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Take the Money and Run (1969)

A handful of nutty moments keep this comedy about a criminally incompetent bank robber above mediocrity (if just). Funniest of all is the bank holdup scene, in which Allen’s robber argues with the bank clerk over the handwriting of his note: “That looks like gub,” the clerk insists. “Not gun.—Cath Clarke

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Radio Days (1987)

It’s the evocation of family life in Brooklyn in the 1940s, the era in which Woody grew up, which lingers long in the mind after seeing this kaleidoscopic, nostalgic portrait of a childhood spent surrounded by everyday eccentrics while dreaming of a distant celebrity world evoked over the airwaves. The familiar cast (Mia Farrow, Diane Keaton, Dianne Wiest) lends it a very personal, homecoming feel.—Dave Calhoun

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20–11

Mighty Aphrodite (1995)

A sparky spin on Pygmalion, with some comic classical references (including an intermittent Greek chorus) thrown in for good measure, this is a witty tale of a man (Allen) who becomes obsessed with the identity of the biological mother of his adopted child. He tracks her down only to discover she’s a ding-a-ling prostitute (Mira Sorvino), whom he feels determined to straighten out.—Dave Calhoun

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Vicky Cristina Barcelona (2008)

Just when Allen fans were about to give up the ghost, along came his best film in a decade. On paper, it reads like one of the director’s ickier old-man fantasies: the story of two young American women in Europe (Rebecca Hall and Scarlett Johansson) seduced by an artist (Javier Bardem) with a crazy ex-wife (Penélope Cruz). But there are flashes of the old genius in this throwaway but enjoyable comedy.—Cath Clarke

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Sleeper (1973)

A health-food store proprietor (Allen) is cryogenically frozen in 1973 and awakens 200 years later when the world has become a police state. Dystopian sci-fi has rarely been so funny: Just try to stifle those laughs when Woody disguises himself as a robotic butler or hides from police in the aptly named Orgasmatron.—Keith Uhlich

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Stardust Memories (1980)

Following directly in the wake of effervescent Manhattan, Allen’s agonized existential-crisis comedy—something of a public meltdown—was destined to turn off part of his audience. But the movie has since found a footing among Woody’s best, not merely as a smart riff on Federico Fellini’s director-as-hero 81Ž2, but as a piece of self-referential hilarity in its own right.—Joshua Rothkopf

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Interiors (1978)

Sandwiched in time between Annie Hall and Manhattan, this was the film with which Woody declared his love for Ingmar Bergman. Wintry, quiet and restrained, with not a hint of a gag (or Woody himself) in sight, it tells of three grown-up sisters who find themselves in a tailspin when their parents unexpectedly announce their divorce.—Dave Calhoun

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Deconstructing Harry (1997)

After years of playing put-upon nice guys, Allen shocked audiences with his portrait of the artist as a resentful, self-loathing creep with a foul mouth and a penchant for prostitutes. Coming in the wake of his brutal public separation from Mia Farrow, this is Woody at his most savage, satirical and self-mocking. A bruising, brilliant film.—Tom Huddleston

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Another Woman (1988)

Further proof that some of Woody’s finest films are those that drop the kvetching men to explore troubled women (see Interiors, Blue Jasmine). This one gives Gena Rowlands a plum role as a feted academic who only realizes that she’s behaved terribly to others when she accidentally overhears a woman (Mia Farrow) talking to her therapist through the walls of her home office.—Dave Calhoun

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Bullets Over Broadway (1994)

“I’m an artist!” shouts John Cusack in the movie’s first line, and over the course of the next riotous 98 minutes, we learn, decidedly, he is not. Allen’s Jazz Age backstage comedy is animated by a trio of inspired creations: Jennifer Tilly’s ditsy gun moll turned theatrical terror; Dianne Wiest’s imperious diva (“Don’t speak!”); and Chazz Palminteri’s gangster poet, hiding the true gift.—Joshua Rothkopf

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Love and Death (1975)

Russian literature takes it in the keister in Allen’s gut-busting satire, in which he plays a coward forced to enlist in the Russian army who also wants to marry his cousin twice removed (Diane Keaton). There’s barely a lull in the laughter, and nothing beats Allen’s internal monologue about wheat.—Keith Uhlich

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10–1

1/10

Blue Jasmine (2013)

Would Blue Jasmine be half as good a film with another actor playing Jasmine, the self-destructive society wife living a champagne lifestyle on lemonade money after her husband is sent to prison? Perhaps not, but Woody Allen lucked out with Cate Blanchett, who gives a brilliant, Oscar-winning, career-best performance.—Cath Clarke

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2/10

Zelig (1983)

Allen stars in this expertly executed mockumentary as Leonard Zelig, a nondescript man with chameleonic powers who shows up in the darnedest places throughout the ’20s and ’30s. He’s a proto–Forrest Gump, rubbing shoulders with everyone from Fanny Brice to Adolf Hitler, and catching the romantic eye of Mia Farrow’s doting psychologist.—Keith Uhlich

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3/10

Sweet and Lowdown (1999)

Off-kilter talents have often found voice in Woody’s work, and the pairing of Sean Penn and a barely known Samantha Morton as, respectively, a 1930s jazz musician and his mute girlfriend is especially winning. The film deals lovingly with the tunes of the period (especially those of gypsy guitarist Django Reinhardt, an Allen favorite), and the faux-doc interview inserts give it a unique touch.—Dave Calhoun

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4/10

Purple Rose of Cairo (1985)

Woody’s at his most optimistic and up-with-people with this fantasy of a downtrodden Depression-era housewife (Mia Farrow) whose world comes alive when the pith-helmeted hero of her favorite movie (Jeff Daniels) steps down from the screen and sweeps her off her feet. The result is both a giddy celebration and a quietly crafty investigation into the effect cinema can have on its audience.—Tom Huddleston

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5/10

Broadway Danny Rose (1984)

A bunch of hardworking comedians kibitz over coffee at the Carnegie Deli. From their reminiscences emerges a wonderful (fictional) tale, about scrappy talent manager Danny Rose (Allen) and his fiercely loyal slate of also-rans. A loving tribute to old-school New York moxie, the film also contains Mia Farrow’s brassy Italian ballbuster, a wild transformation you’ll never forget.—Joshua Rothkopf

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6/10

Husbands and Wives (1992)

This caustic comedy revolves around the romantic tribulations of two married couples played by Allen and Mia Farrow, and Sydney Pollack and Judy Davis. It’s a trenchant examination of long-term relationships on the downswing, something that the real-world tensions surrounding the production (the film was shot around the time of the Soon-Yi Previn scandal) only heighten.—Keith Uhlich

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7/10

Manhattan (1979)

Greatest opening in cinema history? Gordon Willis’s glittering monochrome camerawork combines with Gershwin’s glorious glissandos and Woody’s scalpel-sharp self-mockery to create the ultimate hymn to a city, a sensation, a whole way of life. The remainder of the movie covers familiar ground—romance, self-doubt, intellectualism, despair—with Woody’s customary intelligence and insight.—Tom Huddleston

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8/10

Hannah and Her Sisters (1986)

Here are Allen’s most exquisite performances: nuanced, perfectly balanced, lovably neurotic. There’s not a weak link in the cast, and while it’s a shame to single out an essential performance, it has to be Dianne Wiest’s unsettled Holly, the kind of desperate, flailing Manhattanite that future director-writers would spin entire careers out of.—Joshua Rothkopf

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9/10

Crimes and Misdemeanors (1989)

The film in which Woody’s comic and serious sides most comfortably align, this one tells of two barely connected characters, an eye doctor (Martin Landau) and a filmmaker (Allen), each with intricately messy private lives. Landau handles the doctor’s rising guilt and claustrophobia especially well, while the whole enterprise is entertaining, thoughtful, morally inquiring and hits just the right level of amusing.—Dave Calhoun

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10/10

Annie Hall (1977)

Woody Allen famously wanted to call it Anhedonia, the clinical inability to experience happiness—funny for a film that gives us so much pleasure. This best and best-loved of Woody’s movies is the anatomy of a breakup, beginning at the end of New York comedian Alvy Singer’s relationship with Annie (Diane Keaton, in an iconic turn). It’s packed with gags, and yet there is a painful message at its heart: that meeting your soulmate doesn’t always guarantee a happy ending.—Cath Clarke

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