It’s a great time to be a Woody Allen fan. Not only does September see the release of his new film, Café Society, but also an ‘about-time-too’ Blu-ray collection of his early, funny ones (plus one very serious one) from Arrow Video. Then there’s his first ever multi-episode TV series, ‘Crisis in Six Scenes’, which arrives next month courtesy of Amazon. In light of which, we’ve been hard at work revisiting everything that bears the name of America’s most prolific octogenarian, ranking them from worst to best in an attempt to sort the wheat (“fields of wheat… a tremendous amount of wheat”) from the chaff. So here’s the lot: 46 feature films, an episode from an anthology film, two shorts and a TV movie…

50. Whatever Works (2009)

Although “whatever works, as long as you don’t hurt anybody” is Boris’ (Larry David) motto in Allen’s 2009 attempt at nihilistic comedy, it could not be less representative of the film itself. As the divorced and eternally grouchy Boris finds his quiet life turned upside-down when a young Texan girl (Evan Rachel Wood) finds refuge under his roof, every person he meets is depicted with an obnoxious combination of disdain and insensitivity. Each of their undoubtedly pathetic but nonetheless touching attempts at personal growth is met with sarcasm or straight attacks, which instead of finding humour in human frailty, reveal the backwardness of someone out of touch with modern ideas of love, sexuality and, yes, comedy. The strange dichotomy between Larry David’s vigorous delivery and uncharacteristically static physical performance may indicate a precipitation that could explain the film’s failure. However, Allen’s backwardness in all areas, from gender politics to basic human communication, seems too deep-seated to be an accident. Manuela Lazic

49. Sounds from a Town I Love (2001)

“This is the greatest city in the world! Where else can you be paranoid and right so often?” Made for the Madison Square Garden 9/11 benefit-extravaganza, The Concert for New York City, Allen’s throwaway short sees a host of faces familiar from his filmography marching through NYC, talking on their cellphones. Cramming some 20-odd lame one-liners into its three minute running time, most centred on the city’s post-attack anxieties (“You don’t have anthrax, it’s herpes”), there’s little escaping the sense that it was knocked out one uninspired afternoon. Still, it’s nice to see Allen using Tony Roberts again – for the first time since 1987’s Radio Days – even if it’s for barely 10 seconds. Matt Thrift

48. You Will Meet a Tall Dark Stranger (2010)

It isn’t surprising that the hopeful prediction of this title would lead to disappointment and regret when placed in Allen’s hands. Anxiety abounds here when Sally’s (Naomi Watts) father Alfie (Anthony Hopkins) divorces his wife of many years (Gemma Jones) to pursue his race against time, sparking an uncontrollable and destructive panic in each member of his family. Desperately following their deep-seated and unfulfilled dreams, they start shattering their existence, only to have their illusions of grandeur eventually crushed by the cruel randomness of life. While these character arcs are compelling, the awkward dialogue clashes uneasily with the film’s realist aesthetic. The petty arguments between Sally and her husband Roy (a beautifully curly-haired Josh Brolin) are neither amusing nor touching, but increasingly irritating in their pointless repetition. More worrying still are Allen’s own illusions going – by contrast – undisturbed, as romance and seduction are once again reduced to a power struggle where misogyny is mistaken for flattery. ML

47. What’s Up, Tiger Lily? (1966)

For his directorial debut, a 31-year-old Woody Allen chose to enjoy himself – and in doing so hinted at the direction his filmmaking career would take. The playfulness with form that came to partly define his work constitutes the very foundation of this film: using almost exclusively the images of an already existing Japanese spy film, Allen focuses on editing and dubbing to try and make us laugh. The characters’ new voices, as well as their names, successfully parody the British spy genre, but this superimposition of two different cultures feels like a missed opportunity to explore the connections between the dazzling Japanese genre and its continental counterpart. Instead, the mocking tone, while understandable to the extent that the original film looks very dumb, feels more like mindless fun and repeatedly veers towards racism. Unfortunately, also already present is Allen’s (bad) taste for crass misogynistic humour. The puerile dirty joke with which he closes the film leaves a bad taste, and while he’s rarely so plainly distasteful is his later works, in hindsight this first instance seems like a red flag. ML

46. Cassandra’s Dream (2007)

Allen returns to London in a third bid to nail English as a foreign language. Sliding down the social ladder for a misguided poke around the city’s criminal underbelly, the results aren’t pretty. It’s safe to say that authenticity was not high on the filmmaker’s agenda when casting discussions turned to Colin Farrell and Ewan McGregor. Yet as off-putting a distraction as their accents prove, they’re low on the list of the film’s problems. The screenplay proves the nadir in Allen’s ‘getting-away-with-murder’ series, his direction rarely as disconnected as it so often appears here (witness the bizarre staging of some rained-upon exposition in the park scene). Vilmos Zsigmond keeps things visible while considering his dinner, as Philip Glass juxtaposes the listlessness on screen with a self-plagiarising brand of menace. In fact, everyone’s engagement with the material is best summed-up in Allen’s handling of the key murder scene: when interest threatens, slow-pan to a hedge. MT

45. Hollywood Ending (2002)

“I want a foreign cameraman, because they get a texture into the work,” says two-time Oscar-winning director, Val Waxman (Woody Allen), when striking a deal to direct a potential comeback vehicle. A sleight on Haskell Wexler, fired just a week into Hollywood Ending’s production? Probably not, but there’s a certain irony about this tale of a filmmaker suffering from psychosomatic blindness, given the untold ugliness of the film itself. Replacing Wexler as DoP, Wedigo von Schlutzendorff’s tragic-hour lensing bathes proceedings in a sickly hue, a golden backlighting effect of the kind seen in infomercials selling funeral insurance. Just shy of two hours, the film cries out for Allen’s former editor, Susan E Morse, while limp attempts at auto-satire resemble the kind of thing David Mamet might conjure up post-stroke. As a vision of Hollywood it’s about as recognisable as the respective cities of his European pictures. Only Téa Leoni comes out well; for the film’s people of colour, it’s business as usual. “Who ordered?” asks Woody, overhearing his character’s DoP speak in his native Chinese. MT

44. To Rome with Love (2012)

Exploring love in its many shapes and forms – in marriage, in love at first sight, achieved through fame and recognition, in sex and desire – To Rome with Love refuses to express any of the subtlety of human emotion so keenly felt in the likes of Annie Hall and Manhattan. Of course, that is not a fault in itself, this being a broader, slapstick work, but the film also fails on its own terms as a light comedy of manners. It remains unable to transcend tired jokes about voracious women and sleazy men to transport its surface-level study into any genuinely exciting territory. Alec Baldwin’s aggressively misogynistic, monologue-spitting guardian angel to Jesse Eisenberg’s barely present nebbish is the icing on the cake in a film that awkwardly uses a postcard version of Rome as a blank canvas to paint characters that never speak, behave or feel like real human beings. Elena Lazic

43. Don’t Drink the Water (1994)

Adapted from one of Allen’s earliest screenplays for television, Don’t Drink the Water is a messy, overlong and stagey attempt at imagining the amusing events that may occur if a particularly loud family ended up stranded in an American embassy abroad during the Cold War. Although the premise sounds promising, the film soon loses steam in repetitive and tired jokes. Allen’s character of the grumpy old husband is more unnerving than amusing and the blooming of a romance between the ambassador’s son (an underused Michael J Fox) and the family’s daughter is a cheesy but welcome relief in what is an otherwise unrelenting cacophony. EL

42. The Curse of the Jade Scorpion (2001)

Set in 1940s America with war raging in Europe, this zany story of hypnosis and looted jewels is one of Allen’s most decidedly average films. The director plays an insurance investigator who hides, under his airs of aging and creepy womaniser, a true heart. His new boss (Helen Hunt) is his arch nemesis until each are brought by circumstances to realise that neither of them is as evil as the other believes. The lush cinematography and period setting facilitate the experience during particularly cringeworthy scenes where Charlize Theron shows up, inexplicably wanting to sleep with the old man. The overall film remains a sweet yet not particularly notable work in Allen’s career. EL

41. Anything Else (2003)

Sharing the rather grim nihilism of his angriest late period films, Deconstructing Harry and Celebrity, Anything Else is singular in Allen’s canon for its almost total lack of charm or empathy. A downbeat rom-com in the vein of Annie Hall, the film tracks the doomed relationship of Jason Biggs’ neurotic Allen stand-in Jerry with new girlfriend Amanda (Christina Ricci). But it does so with such ferocity and shrillness as to be at times difficult to watch, despite Darius Khondji’s gorgeous widescreen lensing. Having seduced him away from a ‘nice girl’, the self-absorbed Amanda promptly loses interest in Jerry sexually, inviting her domineering mother to move in with them and frequently cheating. Jerry’s only solace is to be found in bonding with bad-tempered neighbour, David (Allen), who urges him to trust no one and wallow in philosophy. What’s really disturbing is the film’s prompt to sympathise with David and rage against women, here figured as flighty and entirely unreliable. Paul Ridd

40. Melinda and Melinda (2004)

Framed by a boisterous dinner scene between playwright friends, alarm bells ring early in Melinda and Melinda when conversation turns to whether a random scenario, the arrival of an unexpected stranger at a dinner party, would work best as the premise for tragic drama or comedy. It’s difficult to imagine any real-world writers preoccupying themselves with such a banal question, much less so in company, but their argument goes on as the same scenario plays out in two incarnations both unified by the presence of Radha Mitchell as the uninvited guest. In the comic iteration, heartbroken Melinda begins charming married man Hobie (Will Ferrell) away from his wife Susan (Amanda Peet). In the drama, she begins an ill-fated romance with the suave young Ellis (Chiwetel Ejiofor). The problem is that both versions of the story disappoint, the comedy sections lacking any real wit or energy, the drama cursed with that staginess and inertia so characteristic of Allen’s London films. PR

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39. Scoop (2006)

Set alongside sex-and-tennis romp Match Point, psychological thriller Cassandra’s Dream and quirky marital drama You Will Meet a Tall Dark Stranger, Scoop is the fluffiest of Allen’s quartet of London films. Sharing none of those films’ mordant sense of guilt, erotic intrigue or for the most part awful British accents, it’s memorable mainly for an appealing performance from Scarlett Johansson. She lends the rather tired comic plot some much needed zaniness. Still, it’s bit of a slog and a surprise death towards the end proves the only truly remarkable event in an otherwise forgettable work. PR

38. Mighty Aphrodite (1995)

An ageing writer must choose between two beautiful women in their twenties in this extended ‘Pygmalion’ riff which sees Jerry (Allen) attempt to ‘reform’ the mother of his adopted child, hooker Linda Ash (Mira Sorvino) by educating her and sourcing her a suitable partner. When Linda falls in love with him, Jerry must choose to either ward off her advances or cheat on his young wife Amanda (Helena Bonham Carter). Something of an apotheosis of Allen’s potent fantasies of middle-aged male virility, the film combines two of the director’s most troublesome thematic preoccupations. First, there is the cosmic leap that must be made to believe in a particular kind of nebbish older male as being irresistible to young women. Second, there’s an ongoing fixation with presenting endearing naivete in young, sexually voracious women, particularly sex workers. Much of the film’s humour derives from Linda’s shocking frankness when it comes to talking about and having sex, as well as more troubling jokes made at the expense of her ditziness. Much of its awkward pathos comes from Jerry’s protectiveness toward her. PR

37. Vicky Cristina Barcelona (2008)

Much like Midnight in Paris and To Rome with Love, Vicky Cristina Barcelona is as much concerned with conjuring charming, witty characters as it is about presenting a kind of hyper-stylised European tourism on screen. Bathed in golden light and full of breathtaking Spanish vistas, Allen’s lets the story play second fiddle to the locales. Javier Bardem plays moody artist Juan Antonio with an easy intensity, his seduction of ditzy American travellers Vicky (Rebecca Hall) and Cristina (Scarlett Johansson) proving all but effortless. Meanwhile Penélope Cruz appears mid-film as his unstable ex-lover and muse Maria-Elena, enabling a saucy ménage a trois to unfold with Johannson. With a premise veering tastefully on soft porn, the film is salvaged by the excellence (and beauty) of the actors, as well as some snappy dialogue exchanges and fun support from the likes of Patricia Clarkson and Chris Messina. PR

36. Celebrity (1998)

Echoing Stardust Memories and forming a kind of hyper-misanthropic double bill with Deconstructing Harry, Celebrity is Allen’s jet black industry satire, composed of a series of increasingly brutal vignettes in saturated black-and-white, presented with cokey, non-sequential skittishness. Kenneth Branagh plays an adulterous screenwriter named Lee, whose star ebbs and flows even as he encounters various Hollywood grotesques. These range from a polymorphically perverse supermodel (Charlize Theron), to a nymphomaniacal actress (Winona Ryder) via a volatile young film star (an electrifying Leonardo DiCaprio, just on the cusp of adult fame). Partly a brutal rumination on the transient and brutal nature of fame, partly an extended rage against just about every archetype in the entertainment industry, it’s difficult to think of another Allen film so entirely filled with assholes. PR

35. Café Society (2016)

What begins as a light comedy of manners soon goes south when Allen creepily attempts to turn a story of emotional abuse into a heartbreaking tale of two lovers meant for one another. Jesse Eisenberg plays Bobby, a young Bronx native who moves to 1930s Hollywood in the hope of starting a career. When young Vonnie (Kristen Stewart) is momentarily abandoned by her genuinely kind lover Phil Stern (Steve Carell), a rich and married Hollywood producer, Bobby has no qualms taking advantage of his friend’s heartbreak, the two embarking on a short-lived romance together. Although Allen’s self-centred male characters have often been paradoxically sympathetic, the director here repeatedly fails to even acknowledge the awfulness of his lead. Things reach a depressing peak at film end, when the happily married Vonnie inexplicably longs for Bobby, justifying his lifelong bitterness at their separation. At least the crushing bleakness of the story is counterbalanced by cinematographer Vittorio Storaro’s colourful and sunny compositions. EL

34. Stardust Memories (1980)

With this story of a filmmaker reminiscing about his life and his lovers during a festival celebrating his work, Allen borrows heavily from Federico Fellini’s 8½. Unfortunately, he is also seduced by the same pitfalls, and adds to these his own recurrent limitations. Although Gordon Willis’ cinematography manages to echo Fellini’s rapturous images while remaining truly unique and suited to the modern 1980s American context, the tediousness of the loose chronology and repetitions is once again hard to swallow. The self-questioning of a rich, successful male artist who can get any woman he wants was only mildly compelling when he was portrayed by the soulful and heart-breaking Marcello Mastroianni. Replaced by Allen, who adds his usual comedic streak to his predecessor’s performance, the character of the sad director becomes somewhat even more irritating, and his misogyny more blatant and less questioned by Allen’s film than it was by the source material. ML

33. Midnight in Paris (2011)

The attention to detail in costume and production design are unusually ambitious in Midnight in Paris, with the film evoking both a modern and antiquated city. The central conceit, which sees unhappy writer Gil (Owen Wilson) magically transported to old Paris, feels fresh and funny. But it is the shrill depiction of Gil’s flighty and distracted wife Inez (Rachel McAdams) that sours proceedings, coming to define the film’s perspective on male mid-life ennui. Indeed, Gil’s vanity and solipsism are rewarded by a wife-escaping fantasy of Bohemia which lacks any real insight, irony or distance. Offering little commentary on the narcissism, the film seems to share Gil’s worrying nostalgia for a hypothetical past Paris. When Gil eventually leaves the unfaithful Inez, only to promptly pick up a romance with a very young Léa Seydoux, we are invited to rejoice at his good fortune, rather than judge the arrested development made manifest in this gorgeous fantasia. PR

32. Match Point (2005)

One of Allen’s favourite topics is sex, the psychological and physical workings of which he usually explores with humour. For his first London film, however, he chose the dramatic register to portray sexual impulses as antagonistic to the upper class and pernicious for its aspirants. One such determined candidate is Chris (peak Jonathan Rhys Meyers), who endures the boredom of tennis coaching, art galleries and skeet to enter the wealthy Hewett family by marrying the excruciatingly jubilant Chloe (Emily Mortimer). For once, Allen doesn’t shy away from social commentary and contrasts the Hewetts’ complacent opulence with the despair of another wannabe aristocrat, Nola (Scarlett Johansson), a frustrated actress who finds in Chris’ sceptical approach to life an explanation for her own misfortune, and provides him with the excitement his new lifestyle is lacking. Allen’s view of the aristocracy and the world as callous and senseless reaches its dismal apotheosis when Chris, whose basic human decency has been overrun by greed, nevertheless, realises that money will never distract him from guilt – his last remaining trace of humanity. ML

31. Magic in the Moonlight (2014)

While it’s reasonable to argue that the trinket/trifle (delete as personally applicable) that is Magic in the Moonlight may bear a slightness at odds with its lavish production values, one can’t help but be wooed by an aesthetic and directorial commitment that places it at the top of the filmmaker’s Euro-flick deck. Of a piece with the sun-kissed charms and paranormal flirtations of A Midsummer Night’s Sex Comedy, it is undoubtedly a minor work, if one blessed with a collaborative A-game. Relative Team Allen newcomers Anne Seibel and Sonia Grande excel with production design and costume respectively, while cinematographer Darius Khondji atones for To Rome with Love by ensuring the film stands as the best looker on the director’s CV in recent memory. Allen’s screenplay may reduce Emma Stone’s screwball femme fatale to mere narrative cipher, but his fleet-footed staging, deadpan composition and elegantly weaving camera reveal the presence of a master filmmaker too willing to accept his own first draft. MT

30. Shadows and Fog (1991)

An adaptation of his one-act play ‘Death’ featuring Allen as a typically nervy nebbish caught up in the witch hunt for a killer, this sublimely weird oddity/indulgence is one of the director’s most audacious exercises in style. Set against the backdrop of a heavily-stylised, ultra-claustrophobic cityscape, the film visually echoes the work of Fritz Lang and draws on Kafka-esque paranoia, presenting a single individual up against the possible monstrosity of a frightened crowd. Always interesting but often maddeningly self-conscious, a customarily starry cast function as little more than decoration for what is at heart a one trick film. The cast (in particular Madonna, Jodie Foster and Lily Tomlin as a group of tough hookers) are fun but the style is so self-aware, the dialogue so arch and theatrical, that it’s difficult to invest much emotionally. PR

29. Small Time Crooks (2000)

While it’s true that the opprobrium slung at Allen’s DreamWorks period in the first few years of the new millennium is largely deserved, it would be unfair to include his first film for the studio with the painful triumvirate that would follow. A welcome respite from the darker works with which he saw out the last century, Small Time Crooks may run out of steam well before its 90 minutes are up, but it remains a pleasure to witness Allen exercising his funny bone so freely. Allen’s recurring fixation on class and social-climbing is played for centre-stage laughs, while his adroit facility for comic staging is effortlessly showcased in the opening act’s water-thwarted bank robbery hijinks. With its top cast – a show-stealing Elaine May takes MVP – and above average one-liner hit rate, it may not amount to top-tier Woody, but we’d soon discover the value of mid-tier Woody throughout the decade. MT

28. A Midsummer Night’s Sex Comedy (1982)

Gordon Willis’ gorgeous cinematography is the standout aspect of Allen’s reinterpretation of ‘A Midsummer Night’s Dream’, distracting the viewer from the virtually continuous dialogue with his luscious period detail. As three couples spend a weekend together in a country house, old and new tensions surface, as the characters struggle to justify or excuse their impulses. Love and lust, duty and desire, logic and magic clash until things eventually fall into place, each party having learned something new and settled old disputes in the most overwrought ways possible. Allen also displays his impressive talent as an actor in a significantly less neurotic register than we typically associate with his onscreen persona. EL

27. Irrational Man (2015)

Allen’s reflections on getting away with murder go a step further into madness, finally reaching their limit in this odd morality tale. Joaquin Phoenix plays Abe, a depressive philosophy professor going through a profound existential crisis. Emma Stone’s Jill is a young college student charmed by Abe’s cynicism but determined to help him be happy again. As in many of the director’s films, circumstances contrive to have the Allen stand-in only reluctantly accept the advances of a much younger woman begging him to sleep with her. But despite Abe’s own theories about Jill’s attraction to him, she soon reveals herself to be more than a girl crushing on her college professor. In a similar reversal, Abe acts on his misanthropy in a way few other Allen characters would. A violently grim and totally unexpected finale sees Jill prove to be stronger than she at first appeared, and Abe more lost. EL

26. Manhattan Murder Mystery (1993)

A lightweight frivolity, Manhattan Murder Mystery reunited the director with Diane Keaton onscreen for the first time in decades, as a bickering couple sleuthing out a murder plot in their Manhattan apartment block. Sharing the handheld skittishness of Allen’s previous, much darker film, Husbands and Wives, this one bombs along nicely. A stylish final sequence set in the backstage workings of a downtown movie theatre is particularly striking, juxtaposing a screening of the mirror showdown from The Lady from Shanghai with a violent scene of confrontation. There’s also a particularly funny sequence involving the characters’ attempt to blackmail a suspected killer over the phone using tiny strips of pre-recorded sound. But it’s all pretty inconsequential, relying on a fairly witty script, a game cast of Allen regulars and the usual loving evocation of New York City. PR

25. Men of Crisis: The Harvey Wallinger Story (1971)

“You can’t get in to see the president unless you go through Harvey. If Mrs Nixon wants to kiss her husband, she has to kiss Harvey first.” In this unaired short made for PBS Television, Allen plays Harvey Wallinger, close friend and political advisor to Richard Nixon; the only man who can make the president laugh (“He tickles him”). A mockumentary in the Take the Money and Run mode that – with its manipulation of newsreel footage – also looks forward to Zelig, it’s impossible not to sense the undercurrent of anger that runs through The Harvey Wallinger Story, despite its surface silliness. Taking the president’s onscreen faux pas and nonsensical ramblings as his starting point, Allen takes pointed aim at the incompetence of the Nixon administration, highlighting the president’s butter-fingered grip on White House geography. With footage of Nixon garbling his plans for “winning the peace” in Vietnam, Allen translates: “What Mr Nixon means is that it’s important to win the war and win the peace, or at the very least lose the war and lose the peace, or win at least part of the peace or win two peaces perhaps, or lose a few peaces but win a piece of the war. The other alternative would be to win a piece of the war and lose a piece of Mr Nixon.” MT

24. Deconstructing Harry (1997)

As prolific as he is, you could never accuse Woody Allen of being predictable. A year after the joyful Everyone Says I Love You, Allen returned with his most venomous film to date. Once again taking Ingmar Bergman’s Wild Strawberries – a film he mined so successfully a decade earlier with Another Woman – as his starting point, Deconstructing Harry is less a study of emerging self-realisation than a narcissistic nail-bomb of vitriol and self-pity. Yet there’s something perversely admirable about Allen’s willingness to lay bare his baser instincts so unapologetically, the film’s abrasive approach to form as great a fuck you to stylistic pleasantry as his character’s pill-popping misanthropy is to his critics. Blurring the line between fiction and reality, this is Allen at his most structurally audacious. The poison-penned gags mostly land, too – perhaps the greatest of which is delivered by Allen’s writer, Harry Block, describing his protagonist as “myself, thinly disguised”; a worm on a hook for those who took Stardust Memories’ spitefulness to heart. Allen baits his critics to ascribe Harry’s rampant sociopathy to its creator, while chuckling to himself behind the protective shield of artistic privilege. MT

23. Bananas (1971)

Allen’s third film as director, Bananas is more a collection of ideas and sketches than a coherent movie. Allen plays Fielding Mellish, a down-on-his-luck “tester” for various outlandish inventions. Misidentified as a South American dictator in the vein of Fidel Castro, Fielding finds himself suddenly beloved by the people even as he is pursued relentlessly by the US government. Some jokes work, others don’t. A violently chaotic encounter with hoodlums on the New York subway is memorable for a very early appearance by Sylvester Stallone, while some of the early ‘testing sequences’ are perfect exercises in physical comedy. One for die-hard Woody Allen fans only. PR

22. September (1987)

“You can’t tear up everything you write,” says Mia Farrow to Sam Waterston’s novelist. One can only assume it’s a line exclusive to version 2.0, given that September is unique in Allen’s filmography – and surely unique to the cinema – in so far as it was written, shot and mostly cut before being rewritten, recast and reshot wholesale. A miniature, Chekhovian chamber piece indebted to Ingmar Bergman’s Autumn Sonata, it’s a shame we’ll likely never see Allen’s Sam Shepard/Maureen O’Sullivan-starring first pass. At script-level there’s no escaping September’s inherent theatricality, yet it remains blessed with a sharp attention to stylistic detail; a melancholically-imbued sense of the physical and emotional distance between its characters. If the dramatic peaks of its recriminations edge towards hysteria in the latter stages, they’re tempered by the warm tones and a minor-key lyricism that belies the film’s troubled production and subsequent critical savaging. MT

21. Take the Money and Run (1969)

Considering the almost compulsively static aesthetic of Allen’s recent output, it’s hard to believe that the director could ever have made such a frenetic slapstick farce as Take the Money and Run. His second feature is on a par with Everything you Always Wanted to Know… in its episodic structure, but most importantly its absurdist comedy is pushed to the extreme. Most of the jokes consist of Allen’s Virgil Starkwell finding himself in incredibly unlucky situations as he tries and fails to pursue a career as a thief. The film’s series of genuinely funny non-sequiturs are basically Allen’s stand-up one-liners brought to life, recalling the frantic ecstasy of slapstick classics from Blazing Saddles to The Naked Gun in the best way possible. EL

20. Interiors (1978)

“The line between the kind of solemnity I want and comedy is very, very thin,” Allen told Esquire magazine back in 1978. “That’s why it’s so easy to satirise [Ingmar] Bergman. If you bring the drama off, you hit people at the most profound level, but tenth-rate Bergman… is like soap opera.” The film for which Allen took his first critical walloping, Interiors make a lot more sense in the context of his career when viewed with the benefit of hindsight. An unremittingly bleak film, seemingly carved out of ice, it was a bold move coming off the success of Annie Hall. For all the hat-tips to his Scandi-crush that permeate his filmography, nowhere does else does Allen invoke Bergman quite so brazenly. It’s easy to see why Allen detractors might consider it an emotional igloo teetering on the precipice of parody. But for all the film’s overstatement it remains an affecting work of total sincerity, albeit one whose authorial voice often struggles to be heard over the cries and whispers of its influences. MT

19. Love and Death (1975)

Czarist Russia serves as a more barbarian version of Manhattan in Love and Death, Allen’s tale of a man’s life through wars of the nation and of the heart. Boris (Allen) despises his modest upbringing and envies higher society and prettier women, but preferring serendipitous encounters to direct action. Allen doubles down on the film’s grotesque qualities and doesn’t miss the opportunity to throw in cultural references and visual gags. As a result this mostly innocuous comedy is one of Allen’s most effective. Unfortunately, it is once again tainted by several beyond bad taste jokes. ML

18. Blue Jasmine (2013)

An extended, affecting riff on Tennessee Williams’ ‘A Streetcar Named Desire’, Blue Jasmine tones down the melodramatics and sexual tensions to reposition its Blanche Dubois as a ruined New York socialite (Cate Blanchett) forced to rely on the kindness of her working-class sister (Sally Hawkins) when she is bankrupted by criminal husband Hal (Alec Baldwin). Practically a dry-run for Carol, Blanchett brings the full weight of her big, charismatic acting style to the part, ringing maximum pathos and tragedy from the plight of a fierce but fragile woman. Louis CK and Peter Sarsgaard are also excellent in low-key supporting roles, a welcome characteristic of the director’s more recent work. PR

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

In Allen’s films the motivations, functioning and consequences of sexual desire are central to the story, and nowhere more so than here. Taking inspiration from David Reuben’s book of the same name, Allen divides his exploration into seven episodes using different actors, time frames, settings and even dimensions, reaching the cellular level to depict the workings of ejaculation in the last chapter. While he targets fetishes that his sarcasm and taste for embarrassing situations cannot miss – secretive cross-dressing, zoophilia or public lovemaking – Allen also parodies cinema itself. As Dr Ross (Gene Wilder, unforgettable) processes the information that his patient is having sex with a sheep, the camera lingers on his face, his disgust overwhelming the frame to create an indelible moment and one of Allen’s funniest. ML

16. Bullets over Broadway (1994)

In exchange for the money necessary to stage his play, playwright David Shayne (John Cusack) reluctantly gives a role to a mobster’s young girlfriend Olive (Jennifer Tilly) and soon loses control over proceedings in this raucous 1920s-set romp. It’s in the close interaction of social groups that never usually meet – namely actors and the mob – that Allen finds his most amusing observations on desire and self-delusion. Talentless Olive’s wish to be an actress proves simply born of vanity, while the naive Shayne is easily dazzled by the rehearsed airs of once-famous actress Helen Sinclair (a resplendent Dianne Wiest). The only character who truly cares about the play (and art more generally) is mobster Cheech (Chazz Palminteri). Attending every rehearsal as Olive’s bodyguard, he turns out to be a genius playwright himself, and will go to great lengths to make the play as great as possible. Upsetting the social balance, this turn of events makes the film’s atmosphere significantly less stifling and is a satisfying hypocrisy-check for the largely unsympathetic Shayne. EL

15. Oedipus Wrecks (1989)

It is no secret that Allen’s sense of humour relies largely on wordplay: riffing on double meanings or bringing in anachronisms or NY-specific anecdotes, his dialogues often fall into absurdity. Allen nevertheless occasionally attempts to materialise the disconcerting irrationality of his speech into his narratives and visual style. This tendency finds one of its most blatant examples in the short film Oedipus Wrecks, his contribution to the New York Stories anthology. As a man’s anxiety towards his overbearing mother becomes manifest, an impossible wish comes true, a magic trick is actually magic, and New Yorkers somewhat get used to having an old woman looking down on them from the sky 24/7. In the middle of this psychological and physical mess, Allen nevertheless manages to find real sentiment as his character Sheldon asks for the help of a clairvoyant but grows attached to her simply through proximity, time and understanding, and with her help, comes to terms with his Oedipus complex. ML

14. Alice (1990)

Despite the absurd amount of wealth on display in Alice, Allen’s staple interest in the neurotic tales of people with too much money and time on their hands makes it difficult to believe initially that this film might criticise that lifestyle. However, such preconceptions as to Allen’s attitude towards conspicuous wealth only make the film more gripping, as does Mia Farrow’s unexpressive face in the title role. Alice at first seems content with life as a housewife who spends her days buying clothes and beauty treatments. When a severe back pain brings her to a mysterious doctor in Chinatown who prescribes her all kinds of strange concoctions (including one which makes her literally invisible) she soon realises that she is suffering from something much more serious than a pulled muscle. EL

13. Sweet and Lowdown (1999)

Allen’s take on the music biopic is a nuanced exploration of myth-making and its everyday impact on the life of a fictional recording artist. Just as Sean Penn’s talented, but insecure jazz guitarist Emmet Ray begins a relationship with mute lover Hattie (Samantha Morton) – a woman who adores him despite his idiosyncrasies – he heads back on the road, resolved to follow a certain model of the dedicated artist that haunts him. This contrarian tale, where nothing is quite good enough and nothing ever really fits for the hero, is presented on screen with a fascinatingly disharmonious cinematographic scheme of mismatching colours, often colliding greens and reds, yellows and blues. Sean Penn delivers one of the best performances of his career as one of Allen’s most self-absorbed yet most endearing anti heroes. What is initially framed as a superficial, lighthearted faux-biopic turns out to be unexpectedly raw and touching. EL

12. Sleeper (1973)

As its tagline explains, ‘Woody Allen takes a nostalgic look at the future’ in his 1973 comedy. His vision of America circa 2173 is true to the 1970s, as he imagines it populated with clunky, ineffective machines of unpractical shapes and too practical purposes – most memorably the ‘orgasmatron’. This grotesque dystopian future allows Allen to give in to his slapstick impulses, bringing lightness with chases through fields of giant vegetables or across stunning modernist buildings menacingly framed with canted camera angles. Diane Keaton further emphasises this playfulness in the role of a clueless woman dumbed down by modern technology, who then decides to return to nature via a Communist revolution. However, the most gratifying moment remains the simplest: sitting alone with Keaton, Allen once again delivers an interminable string of wisecracks, but finally makes her giggle – not laugh, simply giggle – and at last, these characters seem to connect like real human beings. ML

11. Broadway Danny Rose (1984)

In a filmography that has demonstrated a pervasive pessimism and intense cynicism towards human nature, Broadway Danny Rose stands out precisely because of the unexpected decency of all its characters. In the title role of a talent agent representing a series of hopelessly banal acts, Allen plays an unusually optimistic character, a man who believes in the talent of his artists with an inextinguishable fervour, despite being perpetually abandoned in favour of more fashionable agents. Expressing none of the disdain for small victories typical of Allen’s characters, Danny does all he can to help jazz singer Lou Canova (Nick Apollo Forte) navigate a nostalgia wave that has hit tiny New York clubs. The complete altruism of this comically selfless agent is genuinely endearing. But the film’s real success lies in its empathy towards every single character. EL

The Top 10…

10. Everyone Says I Love You (1996)

Considering the omnipresence of jazz in his soundtracks, Allen was bound to eventually indulge his passion further with a jazzy musical. Between New York, Venice and Paris, Joe (Allen) and his dysfunctional family try to fulfil their desires and live with their choices. Ex-wife Steffi (Goldie Hawn), happily remarried to Bob (Alan Alda), is convinced that Joe isn’t over her; but is she over him? Meanwhile, their daughter Skylar (Drew Barrymore) is about to marry the gauche but devoted Holden (Edward Norton) but is troubled by her fantasies. And so is Vonnie (Julia Roberts) who has the bad luck of finding her most secret desires suddenly fulfilled by a desperate and scheming Joe. The creepiness of his seduction is perfectly ridiculed when Joe attempts to bump into her while jogging but, in a montage Jacques Tati would have been proud of, gets lost in the labyrinthine Venice. However unfulfilling fantasies turn out to be, Allen’s characters end up realising that they will always cherish and honour them with a melancholy tune. ML

9. Radio Days (1987)

After channelling 8½ for Stardust Memories, Allen turns to Fellini’s Amarcord for his most personal film. A wistful tribute to radio in the time of his youth, Radio Days takes the form of a series of vignettes, narrated by the filmmaker and bathed in a nostalgic glow. Casting a young Seth Green as the Allen avatar allows for a welcome shift in perspective; a heartfelt evocation of childhood imbued with a bittersweet fondness for a lost era that deftly avoids sentimentality. The film dances between autobiographical reminiscence and apocryphal tall tales: from the pair of burglars who find themselves on a gameshow when they answer the phone on a job, to the unlucky-in-love persistence of the wonderful Dianne Wiest. The power of music to conjure sense-memories is stunningly evoked; nowhere else does Allen transmit his love for the great American songbook with such a genuine sense of longing, loss and affection. MT

8. The Purple Rose of Cairo (1985)

What makes cinema so fascinating is its power to plunge you in a different world, far from and better than your own in some way. Following his tendency to take expressions literally for dramatic effect, Allen imagines a movie, The Purple Rose of Cairo, coming to life. The limit between fantasy and reality used to disappear only to an extent for Cecilia (Mia Farrow), when every evening, she would find refuge in her local movie theatre to forget the Depression and her lousy husband (Danny Aiello) for a couple of hours. Now, in an avenging twist of fate, her desperate binge-watching has brought her favourite character, the courteous Tom Baxter (Jeff Daniels), off the screen and into her arms. Yet just as her fulfilled dream brings her the courage to seek a better (real) life, a reality-sourced hope appears in the shape of Gil Shepherd, the actor playing Baxter (Daniels again, but this time electrifyingly arrogant). But Cecilia’s choice between the two men is one between two impossible illusions: while Baxter still isn’t real, Shepherd is just a man (and an actor!) whose consistency of character isn’t guaranteed like Baxter’s is by a script. This may be Allen’s most profound, gratifying and affecting reflection on the double-edged nature of fantasies, at once comforting and destructive in their perfection and unreachability. ML

7. Husbands and Wives (1992)

Simultaneously one of Allen’s most mature and punishing examinations of relationships in turmoil, Husbands and Wives signals its temperament before the opening shot, as Cole Porter’s ‘What is this Thing Called Love?’ plays over the title cards: “I saw you there one wonderful day / You took my heart and threw it away.” Then comes the abrasive interrogation of Carlo Di Palma’s handheld camera; the fallout as Jack (Sydney Pollack) and Sally (Judy Davis) announce their separation to friends Gabe (Allen) and Judy (Mia) captured in its unmoored glare, sans cut. It’s difficult to separate the film from the context of its production – during which the Allen-Farrow scandal made worldwide headlines – not least given its aggressive disregard for stylistic pleasantries. It’s a formal approach that effectively conveys the emotional bruises these characters routinely inflict upon each other; even as Allen allows a capacity for emotional growth all too rarely seen elsewhere. This maturity is best exemplified by Gabe’s relationship with his young student, Rain (Juliette Lewis). The student-teacher affair is a common enough Allen trope, but Gabe’s rebuttal of the razor-sharp, infatuated girl’s advances feels refreshing. MT

6. Zelig (1983)

Allen’s nostalgic cinephilia always comes through in his films via references, parodies or plays with form. With wit and tenderness, Zelig demonstrates his passion for both documentary and the 1920s as he adopts the newsreel format to present a strange story of false identity through key historical events up to the ’30s. As psychoanalysis is burgeoning, Leonard Zelig (Allen) finds himself the subject of tests by Dr Eudora Fletcher (Mia Farrow) when she discovers that this socially troublesome character is in fact a chameleon, capable of blending in with crowds by adopting their vocabulary, physical aspect and race. Behind the slapstick of Allen turning into a proto-intellectual, an obese or a Chinese person – transformations fairly acceptable given the film’s ironic immersion in old-fashioned mores – and becoming a freak for the New York elite, a moving commentary on social anxiety appears. With Eudora’s help and talent, however, Zelig will find his balance and, in return, give her the recognition she had long been fighting for in a male-dominated field. ML

5. Annie Hall (1977)

What makes Annie Hall unique is the presence of a character who actually giggles at Allen’s wisecracks. Herein lies the secret to the film’s success. Allen’s Alvy Singer (a character so autobiographical the director actually has him be a stand-up comedian) for once isn’t making jokes at the expense of the other characters and for the viewer’s amusement. Rather, Diane Keaton’s Annie gets him, just as we do. Recalling the beginning and end of a love story with great tenderness, the film shows both partners as flawed in some ways. Yet Allen the director is deeply self-aware about Alvy’s, and supposedly his own, destructive behaviour. When in the film’s closing moments, Alvy stubbornly maintains that he does not understand what happened, his melancholy and the film’s self-reflexivity heartbreakingly imply that he understands perfectly well, but can’t seem to face what he did, and what he has lost. EL

4. Another Woman (1988)

The greatest of Allen’s homages to his idol, Ingmar Bergman, Another Woman takes the thematic skeleton of the Swedish director’s 1957 masterpiece, Wild Strawberries, as the template for an exquisite meditation on empathy, aging and regret. Gena Rowlands plays Marion Post, a successful philosophy professor and writer just turned 50. She lives a life of financial and academic privilege, oblivious to the long-held resentments of those around her. Unable – or unwilling – to face the crisis of self-awareness forced upon her through a series of recriminations and late realisations, Marion tunes in to the voice of a suicidal woman, whose therapy sessions she can hear through the ventilation duct of her rented workspace.

Like Bergman, Allen transmits Marion’s interior life through her narration; a plainly-spoken, almost diaristic accounting of events and emotional impassivity. Wild Strawberries’ famous dream sequence takes the form of a stage play recounting Marion’s failed relationships, while her cold intellectualism and incapacity for self-awareness is poignantly contrasted in the tears found on the final lines of her mother’s favourite Rainer Maria Rilke poem: “…for here there is no place that does not see you. You must change your life.” Running a mere 81 minutes, it’s Allen’s most controlled and understated work, not least thanks to Rowlands’ subtle exposure of emotional fault lines and DoP Sven Nyqvist’s steely reserve. Not a film of forceful confrontations but one of gentle realisations, delivered with the kind of melancholy sigh exemplified by Marion’s ageing father’s heartbreaking soliloquy: “Now that my life is drawing to a close, I’ve only regrets…” MT

3. Manhattan (1979)

A bittersweet romantic comedy about self-absorbed New York writer Isaac (Allen), Manhattan is beyond doubt the director’s most rapturous tribute to his city and particular social milieu. But beyond the breathtaking cinematography, witty script, beautiful acting and score, it also remains the clearest and most concise presentation of his core shtick. As Isaac leaves his doting, very young partner Tracy (Mariel Hemingway) to pursue a brief, doomed fling with the neurotic Mary (Diane Keaton), the film lays bare the fragile nature of his and others’ desire and jealousy, while somehow remaining a film that is light and funny throughout, despite its comparatively pessimistic outlook on human relations.

In one of Allen’s most tenderly written scenes, Isaac falls out spectacularly with his best friend Yale (Michael Murphy) who splutters “I saw her first” in defence of his adultery with Mary. The men find themselves actually speaking like children where before they had simply acted as such. It’s a bracingly self-aware moment, the scene’s insight into fragile, borderline ridiculous masculinity proving more progressive and revealing than much of the director’s work since. Yet Allen cannot resist concluding on a note of almost unbearably romantic optimism. It is Tracy’s sentiment, “You gotta have a little faith in people,” that expresses with a perfect clarity the core misery of the characters, as well as a possible solution, within this movie and beyond. There is no ending like it. PR

2. Crimes and Misdemeanours (1989)

One only need look at Melinda and Melinda or Cassandra’s Dream to see how easily Allen’s films borne out of an overarching philosophical or dramatic thesis can swiftly head south. Crimes and Misdemeanours is an exception to the rule – and what an exception. Taking his cue from Fyodor Dostoyevsky’s ‘Crime and Punishment’, Allen fashions his own Raskolnikov in Martin Landau’s Judah Rosenthal, an ophthalmologist plagued with guilt over the murder of his mistress. The film’s forked structure sees the drama of Judah’s story counterpointed in a parallel comic narrative that follows a filmmaker (Allen) as he unwillingly shoots a documentary on his successful, boorish brother-in-law (Alan Alda).

Allen sets up a series of dialectical oppositions as a means of exploring the film’s themes: the absence of morality in a godless world; faith versus doubt in human nature and man’s capacity for goodness; the gulf between the cathartic resolutions afforded by cinema and the mess of reality. If such existential enquiries suggest an academic exercise on paper, Allen’s extraordinary screenplay integrates and embeds them seamlessly. It’s one of the filmmaker’s darkest, most cynical pictures, but also one of his funniest. As the two narrative strands coalesce for a final scene between Allen and Landau, this amorality play pointedly disavows resolution, even as it continues to probe questions of ownership and authorship in life and art. “We define ourselves by the choices we have made. We are in fact the sum-total of our choices,” we hear in voiceover, as the film fades out on Sam Waterston’s blind rabbi dancing at his daughter’s wedding: the one figure who finds contentment – however foolishly – in the moral imperatives of a higher power. MT

1. Hannah and Her Sisters (1986)

It took a while for Woody Allen to escape from the shadow of his influences, to forge a masterpiece indebted to his love of Bergman and Chekhov, but one which stands apart as a summation of his own work to this point and beyond. While Interiors may have marked the point at which Allen made a bid for artistic maturity (whatever that might mean), Hannah and Her Sisters was the moment the director stopped seeing his comic and tragic inclinations as mutually exclusive modes, delivering a film in which the organic codependency of both reaps the richest of rewards.

In its thematic preoccupations, the film is quintessential Woody: the quest for meaning in a spiritual void; the obsession with mortality; the conflict between the intellectual and emotional realms; human fallibility and the elusive search for self-fulfilment through sex and attachment. Yet here, Allen’s nihilistic tendencies are tempered by an optimistic humanism untainted by his go-to defence mechanism of sentiment cloaked in nostalgia; it’s a romantic movie, but one that tugs at the heart strings by virtue of its realism in the way the characters and relationships are drawn, not by a romanticism afforded by form. “You’ve got to have a little faith in people,” says Mariel Hemingway’s Tracy at the end of Manhattan; Hannah and Her Sisters is that faith manifest. MT

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Published 30 Aug 2016