The best Woody Allen movies of all time

From nourishment to nebbishment (and all points in between), we rank the comedian-director’s 45 features
The best and worst Woody Allen movies
By Time Out contributors, edited by Joshua Rothkopf |
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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 romantic movies, dramas and comedies that follow? We’ve got opinions. Take a trip through our countdown of the best Woody Allen movies: his ups, his downs, his New York movies, his Academy Award winners, his essential masterpieces.

Best Woody Allen movies: 45–31

45
Movies

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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44
Movies

Whatever Works (2009)

Larry David’s indifferent shrug on the film’s poster tells you all you need to know about one of the Woodman’s worst. On paper, the combination of David and Allen seems can’t-lose, but only sourness emerged from the real thing. Ingrained with bone-deep misanthropy, it’s hard to imagine this project being any better had the director made it in the 1970s with Zero Mostel, as he originally intended.—Joshua Rothkopf

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43
Cassandra's Dream
Movies, Drama

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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42
Anything Else
Movies, Drama

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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41
Hollywood Ending
Movies, Comedy

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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40
A Midsummer Night’s Sex Comedy
Movies, Comedy

A Midsummer Night's Sex Comedy (1982)

The first film of what we can now call Woody’s “Mia Period” didn’t exactly promise great things; it’s a scattered, soufflé-light affair, aping Bergman’s Smiles of a Summer Night without seeming to understand it all that well. Still, it’s refreshing to see Allen in a non-neurotic mood and, within the totality of his career, the film is refreshing.—Joshua Rothkopf

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39
Melinda and Melinda
Movies

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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37
The Curse of the Jade Scorpion
Movies, Drama

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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36
To Rome With Love
Movies, Comedy

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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35
Movies, Comedy

Magic in the Moonlight (2014)

A lighthearted romance set in 1920s Germany and France, this is one of Allen’s most charmingly performed efforts. Our hero, Stanley (Colin Firth, amusingly pompous), is a popular stage magician whose task is to debunk a self-proclaimed psychic named Sophie (Emma Stone). Yet try as Stanley might, he’s unable to uncover her trickery, and with each new “miracle” she performs, he falls deeper in love. It’s a simple premise that Allen complicates with an illusionist’s expertise.—Keith Uhlich

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34
Match Point
Movies, Drama

Match Point (2005)

Finally, a Woody Allen film to get verklempt about. His prior years had been hard on fans, harder on critics, but he returned to form with this thriller set in the richly appointed drawing rooms, tennis courts and yachts of the English upper class. (Er, who is this Woody guy anyway?) In swapping Manhattan for a slightly more expansive island, the director got closer to his career-long obsessions with Bergmanesque guilt and cosmic absurdity.—Joshua Rothkopf

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33
September
Movies, Comedy

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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32
Shadows and Fog
Movies, Comedy

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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31
Movies, Drama

Everyone Says I Love You (1996)

Woody makes a rare foray into the world of musicals, in which actors not known for their soft-shoe or songbird voices (Drew Barrymore, Alan Alda, Edward Norton, the director himself) start dancing and warbling at the drop of a hat. Not as bad as you’d think, but it wouldn’t make anyone’s Allen A-list.—Joshua Rothkopf

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Best Woody Allen movies: 30–21

30
Irrational Man
Movies, Drama

Irrational Man (2015)

Woody's latest philosophical exercise strikes a balance between the darkness of Cassandra's Dream and the jazzy frivolousness of just about every film he's made since. The story of an unmoored professor (Joaquin Phoenix) who arrives at a Rhode Island university for a new gig and promptly sleeps with Parker Posey, seduces Emma Stone and makes a killing, Irrational Man goes down pretty easy for a movie about the morality of murder.—David Ehrlich

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29
Small Time Crooks
Movies, Comedy

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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28
Midnight in Paris
Movies, Comedy

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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27
Celebrity
Movies, Comedy

Celebrity (1998)

Inexplicably selected to open that year’s New York Film Festival, this wan, frequently tedious portrait of those on fame’s margins features a performance by Kenneth Branagh that’s probably the most irritating Woody impression ever committed to film or video. Then again, Leonardo DiCaprio makes the movie essential and revealing as a hotel-trashing bad boy (i.e., Leo in his Pussy Posse days).—Joshua Rothkopf

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26
Bananas
Movies, Comedy

Bananas (1971)

A peppy Marvin Hamlisch score propels this early gutbuster, which finds the Woodman leading a revolution in an unnamed South American country. For the record, that’s actually Howard Cosell as Howard Cosell in the sports-commentary parody of an intro—not Jon Voight or John Turturro or whoever’s played him onscreen since.—Joshua Rothkopf

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25
Manhattan Murder Mystery
Movies, Comedy

Manhattan Murder Mystery (1993)

Allen reunited with Diane Keaton for the first time since the advent (and departure) of Mia for this trifle, which was reworked from material cut from Annie Hall. Woody can make delightful NYC comedies in his sleep, and even if less charitable viewers would say that’s exactly what he did, there’s still a ton of great zingers here, as well as a bumbling sense of Upper West Siders getting in over their heads.—Joshua Rothkopf

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24
Alice
Movies, Comedy

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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23
What's Up, Tiger Lily?
Movies, Comedy

What's Up, Tiger Lily? (1966)

It’s not entirely accurate to say that Woody “directed” this spoof, since it’s actually a Japanese spy flick (Key of Keys) with ridiculous overdubbed dialogue courtesy of the funnyman and his pals. Inspired and sophomoric by turns—the plot turns on a hunt for the world’s greatest egg-salad recipe—it’s the bastard step-parent of MST3K.—Joshua Rothkopf

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22
Take the Money and Run
Movies, Comedy

Take the Money and Run (1969)

Woody’s first major comedy is full of important lessons for the beginner criminal: When breaking out of prison during a rainstorm, don’t use a gun carved out of soap. Make sure that another gang isn’t going to rob the same bank, on the same day and at the same time. And for Pete’s sake, check your spelling! (“I am holding a gub on you.”)—Joshua Rothkopf

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21
Radio Days
Movies, Comedy

Radio Days (1987)

The Woodman’s nostalgic tribute to the home entertainment medium of his childhood consists almost entirely of self-contained anecdotes, ranging from the hilariously irreverent (“You speak the truth, my faithful Indian companion,” says the young hero to his rabbi) to the somberly poignant (the nation awaits the fate of a child trapped in a well).—Joshua Rothkopf

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Best Woody Allen movies: 20–11

19
Mighty Aphrodite
Movies, Comedy

Mighty Aphrodite (1995)

Truthfully, the Greek chorus gets unfunny pretty fast. But Mira Sorvino’s sweet ding-a-ling prostitute proves that Allen is a giant when it comes to directing women. In a subtle way, this comedy comments wisely about the unfixable nature of people; the plot brings us closer to being okay with exactly who we are.—Joshua Rothkopf

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18
Vicky Cristina Barcelona
Movies, Drama

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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17
Sleeper
Movies, Comedy

Sleeper (1973)

Perhaps the finest of Woody’s “early, funny” pictures, Sleeper finds his standard nebbish cryogenically awakened in the year 2173, when he discovers the Orgasmatron and various other sci-fi gags. Per usual, Allen employs a jazzy soundtrack, though he opts for Dixielandish tunes over Gershwin ditties this time.—Joshua Rothkopf

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16
Stardust Memories
Movies, Comedy

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 8½, but as a piece of self-referential hilarity in its own right.—Joshua Rothkopf

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15
Interiors
Movies

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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14
Deconstructing Harry
Movies, Comedy

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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13
Another Woman
Movies, Comedy

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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12
Bullets Over Broadway
Movies, Comedy

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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11
Love and Death
Movies, Comedy

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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Best Woody Allen movies: 10–1

10
The best and worst Woody Allen movies
Movies, Drama

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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9
The best and worst Woody Allen movies
Movies

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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8
The best and worst Woody Allen movies
Movies

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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7
The Purple Rose of Cairo
Movies, Comedy

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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6
Broadway Danny Rose
Movies, Comedy

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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5
Husbands And Wives
Movies

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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4
The best and worst Woody Allen movies
Movies, Comedy

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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3
migrate.36915.jpg
Movies

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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2
The best and worst Woody Allen movies
Movies, Comedy

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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1
The best and worst Woody Allen movies
Movies, Comedy

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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