The best and worst Woody Allen movies

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

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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 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

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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42

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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41

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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40

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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39

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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38

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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37

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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36

You Will Meet A Tall Dark Stranger (2010)

Possibly the best thing you can say about this film is that it’s the least bad project from Woody’s London phase. A comedy with a taste as bitter as arsenic, it has thinly drawn characters navigating marriage failures, the search for love and fortune-telling. Not wholly terrible.—Cath Clarke

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35

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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34

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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33

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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32

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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31

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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