Woody Wednesday All 47 Woody Allen movies – ranked from worst to best Part D

(L-R): Annie Hall, Sleeper and Vicky Christina Barcelona
(L-R): Annie Hall, Sleeper and To Rome With Love

Annie Hall or Bananas? Blue Jasmine or Sleeper? Our critics Robbie Collin and Tim Robey rank all 47 Woody Allen movies

25. Sleeper (1973)

The first film in which Allen directed Diane Keaton was also, perhaps not coincidentally, the first film to suggest he had more in him than than madcap, gag-driven comedies. (They appeared in a film together before his directing days). That’s not to say Sleeper isn’t as madcap and gag-driven as his earliest work: a film about a health food shop owner who falls into a vat of liquid nitrogen and wakes up 200 years later kind of has to be. But Allen’s painting with new colours here: romance, melancholy, and even – gasp! – coherent plotting, while the uproarious robot butler sequence showcased his talent for silent-era physical clowning.

24. Everything You Always Wanted to Know About Sex* (*But Were Afraid to Ask) (1972)

This anthology of seven sketches on a raunchy theme, loosely based on a best-selling bedroom manual of the day, has grown grubbier with age. But watched with a generous and forgiving eye, its legendary popularity (in the US, it was one of the 10 most successful films of its year) still makes sense. And three sequences still burst with visual ingenuity and laughs: an Italian cinema spoof, the famous science-fiction-like scene in which Allen plays a sperm on date night, and Gene Wilder’s tender love affair with a sheep.

23. Midnight in Paris (2011)
Midnight in Paris

Depending on your point of view, this huge hit and Oscar Best Picture nominee – Woody’s first in a quarter-century – is either glass-half-full or half-empty Allen: an enjoyable, shiny bauble in which time-travel back to the Jazz Age reveals the grass to be always greener; or a shallow, rather pseudy coffee-table conceit whose present-day characters are cut-out irritants. Adherents to both viewpoints were surprisingly passionate, but there’s not all that much separating them, in truth. Owen Wilson’s jaunty flâneur takes the whole thing in his stride: hard not to, when Allen’s throwing so many easy conquests in his direction.

22. Bananas (1971)

Perhaps of all Allen’s early comedies, this is the one that could be remade today with the fewest concessions to modern taste. That might be because on its release, it already felt like a film out of time: it’s effectively the Marx brothers’ Duck Soup with a Cuban spin (Allen’s wilting New York nebbish accidentally becomes a dictator) and survives on its never-ending supply of lunatic gags, thundering past like an express train. It looks cheap, which is funny in itself, and satire and spoofery are crammed in until it bulges at the seams.

21. Deconstructing Harry (1997)

Allen’s sourest comedy is one of his more arresting, certainly of the increasingly wayward 1990s: it touches a few raw nerves. The structure is roughly lifted from Bergman’s reflections on a life in Wild Strawberries, as Allen’s flailing writer, Harry Block, is invited back to his alma mater to receive an honorary degree. This trip involves reckoning with the fallout from Harry’s failed relationships, not to mention some wacky swerves into sketch comedy – Robin Williams develops the medical condition of being out-of-focus, and Tobey Maguire plays a sex-obsessed alter ego. It’s an uneven grab bag, a flawed film à clef with biting and honest moments.

20. Cafe Society (2016)

It’s the Thirties, and young Bobby Dorfman (Jesse Eisenberg) has abandoned the sepia-tinted hubbub of the Bronx for the Technicolor vistas of Hollywood. After arriving in town, Bobby seeks out employment from his uncle Phil (Steve Carell), a bulldoggy agent who doesn’t so much drop names as scatter them in his wake like confetti. Work is hard to come by, but in the meantime Phil puts Bobby in touch with his secretary Vonnie (Kristen Stewart), who offers to show him the sights.

Cafe Society

After a run of russet-hued collaborations with cinematographer Darius Khondji, Allen is working here for the first time with the venerable Vittorio Storaro, and the change has done him the good. A couple of scenes with Bobby and Vonnie together are the most visually beautiful sequences in an Allen film in goodness knows how long. And then there’s Stewart, who’s the best thing here from the moment she steps on screen. (Read the full review)

19. Love and Death (1975)

The smartest of Allen’s early run of scattershot comedies is a surprisingly accessible send-up of the Russian literature he was devouring at the time, and which would go on to shape his later, weightier work. Allen is Boris Grushenko, a “militant coward” who’s sent off to fight the French, and ends up involved in a plot to assassinate Napoleon with the help of his pretty cousin (Boris: “twice removed!”), played by Diane Keaton, who’s well on the way to the height of her comic powers. Parodies of Tolstoy, Eisenstein and Bergman rub shoulders with some vintage surreal and bawdy Allen riffs.

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