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Ranked: Woody Allen Films from Worst to Best

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With Midnight in Paris hitting theaters this week, we look back at everything from Annie Hall to Match Point.

Woody Allen has written and directed forty-one films in the last forty-five years, making him one of our most prolific auteurs. He's also run the gamut between great and awful more perhaps than any other director. With his latest, Midnight In Paris, out this Friday, I sized up the man's formidable body of work, listed here from worst to best.

 

41. Cassandra's Dream (2007)

Sometimes you really do wonder what goes through Woody's head when he's working on a script: "What should I recycle? A little murder from Crimes and Misdemeanors? A little guilt complex from same and Match Point?" An insipid retread of those two excellent films, Cassandra's Dream is a movie Woody had already made twice, with no room to improve. Woody on full autopilot; it's a terrible picture by any standard.

 

40. Whatever Works (2009)

Some people say there's no such thing as a bad Woody Allen movie, just weaker and stronger ones. To which I say: watch Whatever Works. Screwing up as exciting a combination as Larry David and Woody Allen is practically inconceivable, but David feels totally off (strangely) in the Woody surrogate role, and Evan Rachel Wood (otherwise a fantastic actress) plays like a caricature. It also seems criminal to waste the talents of Harris Savides — the world's greatest working director of photography — on this. The one-liners are as clunky as they've ever been.

 

39. September (1987)

Woody shot this film, edited it, and then decided he had to shoot it again with a different cast. He should've just shelved the thing entirely. Taking place in one summer house with a interconnected web of people who all have attractions to each other, it aims to be an unaffected character study, but comes across as narcissistic. That's always the danger of making the type of movies Allen makes — movies simply about the relationships of little people in an indifferent world. His filmmaking is stronger when he doesn't seem to invest those relationships with deep, undeserved meaning.

 

38. A Midsummer Night's Sex Comedy (1982)

Despite what the title might have you believe, this is not in the same realm as wacky Woody flicks like Bananas — rather, it's an uncertain, confused film that falls somewhere between a screwball comedy and a more straightforward entangled-relationships drama.

 

37. Midnight In Paris (2011)

Neither a comedy nor a drama, this fantasy-romance plays like a C-grade version of The Purple Rose of Cairo. Owen Wilson is miscast as a neurotic-yet-romantic screenwriter, and the story feels thin, with a love interest (Rachel McAdams) who has about as much characterization as an electrical appliance. The most interesting character (Michael Sheen) basically vanishes after the first act. There are occasional laughs, and Darius Khondji's photography of Paris is fantastic, but those are the few bright spots.

 

36. The Curse of the Jade Scorpion (2001)

This film was derided by many, and Allen's called it his worst. I wouldn't go that far — the screwball form always lets him at least slip in some solid one-liners — but the jokes fall flat here more often than in similar faux-noir farces like Manhattan Murder Mystery and Small Time Crooks. Jade Scorption concerns a hypnotist who exerts mind-control over Allen's insurance investigator as well as his co-worker (Helen Hunt) to make them steal jewels for him. It's about as sensible as it sounds.

 

35. Melinda and Melinda(2005)

Points to Woody for an ambitious narrative construct — he tells the same story twice, once as a comedy, once as a drama — but no points for anything else, frankly. Will Ferrell, pre-mega-fame, hews too close to the traditional Woody persona in the comedic section, and the dramatic half aches of melodrama.

 

34. What's Up, Tiger Lily? (1966)

Technically the first film Woody directed, Tiger Lily is actually a mash-up of two Japanese spy movies that he recut and overdubbed; the plot is utterly absurd, and the whole film is basically just a vehicle for Woody to play off of the bizarre image/dialogue juxtaposition. Slightly dated at this point, but the strength of the best lines — "They kill, they maim, and they call information for numbers they could easily look up in the phone book!" — ensured that he would be able to keep making films.

 

33. Alice (1990)

A more fantastical version of the stronger Another Woman, Alice is another example of Woody trying to make a film he often struggles with: the well-off-person-trying-to-gain-perspective movie. Here, the protagonist is a wealthy housewife whose dalliance with magical herbs provides her with the strength to push herself outside her comfort zone — because, Allen seems to be saying, she's not strong enough to do it herself. While the emptiness of materialism is an interesting subject, the goofy magic-herbs device undermines what Allen is trying to deal with.

32. Shadows and Fog (1992)

The Allen film you're least likely to have heard of certainly stands apart from the rest. Taking place during one night, and adapted from Allen's play Death, it revolves around a town embroiled in a search for a killer, the Strangler. Allen's character is linked to the Strangler's most recent victim, and must avoid both the mob that's after him as well as the Strangler himself. The feeling of dread is palpable but often overwrought.

 

31. You Will Meet A Tall Dark Stranger (2010)

This is a middling picture that, frankly, would be a hell of a lot better if it hadn't been made by Woody Allen. (You try to treat every film as its own entity, but with Woody's constant self-plagiarizing it's almost impossible.) Stranger has its moments of complexity, but for the most part it's a dull walkthrough of themes — infidelity, fear of commitment, fear of loneliness, career ambition — that Allen has dealt with continually, and almost always in better works.

 

30. Interiors (1978)

How do you follow up earthshaking success? After dipping into drama with Annie Hall, Allen pushed further with this film, revealing strengths (character observation, existential dread) that would fully blossom later in his career, but also limitations — Woody is not Ingmar Bergman, and after making this film about three adult sisters who all work in various arts, he would never try to be Bergman again, at least in such an audaciously obvious way.

 

29. Small Time Crooks (2000)

This tale of a bank robbery gone wrong isn't a disaster. Woody's performance as an uncultured ignoramus is a refreshing break from his usual persona. And though it does feel a bit like Allen (a wealthy and famous artist) is poking fun at "the masses" with his portrait of the working-class ensemble, there are nevertheless some laughs in good fun. Elaine May's great as the dimmest bulb of the bunch.

 

28. Mighty Aphrodite (1995)

This film marked a turning point in the '90s when Allen's work started to feel like it was straining. The tale of a writer whose adopted son's biological mother turns out to be a prostitute, it has some bright spots — the amusing usage of a Greek chorus, for one — but ultimately feels like it's going through the motions, especially in the portrayal of Woody's relationship with his wife, played by Helena Bonham Carter. Mira Sorvino won an Oscar for her performance, which is certainly the film's greatest strength.

 

27. Celebrity(1998)

One of Woody's darker pictures, and his most recent to be shot in black and white, Celebrity flopped on release, but has its moments. Kenneth Branagh is amusing, though a bit obvious, in the stand-in-for-Woody role. Bitterly satirical, the film tries to send up the superficiality of modern fame, but often comes up short. The sequence with Branagh wooing Charlize Theron is great though.

 

26. Another Woman (1988)

This ambitious drama about a middle-aged woman's depression doesn't quite work, but it still offers some interesting psychological portraiture. Gena Rowlands is solid as the protagonist, while the rest of the cast — including Ian Holm as her husband, Gene Hackman as her former lover, and Mia Farrow as a woman whose psychotherapy sessions Rowlands begins eavesdropping on — creates interesting characters who still don't feel fully fleshed out.

 

25. Take The Money And Run (1969)

A faux-documentary about an utterly inept criminal (played by Allen), this was the first film Woody truly directed (as compared to What's Up, Tiger Lily?). While his absurdist style still feels a little rough — it wouldn't truly coalesce until Everything You Wanted To Know About Sex — the film was still strong enough to indicate where this brash young filmmaker was heading. The famous holdup-typo scene is particularly hilarious.

24. Bullets Over Broadway (1994)

Few filmmakers are as preoccupied with genius and its trappings as Woody Allen. This funny, though flawed, film focuses on the behaviors that artists believe they're entitled to once they've been validated as geniuses. Chazz Palminteri's performance, as a gangster who turns out to be a brilliant playwright, is inspired.

 

23. Sweet And Lowdown (1999)

Allen strayed from his comfort zone to direct this dramatic picture about a troubled jazz musician, a somewhat bright spot in his '90s work. Allen's personal passion for jazz comes across in the film's period-perfect music, but Sweet And Lowdown's leads, Sean Penn and Samantha Morton, really carry it.

 

22. Radio Days (1987)

Similar in tone to the stronger Purple Rose of Cairo, Radio Days was another mid-'80s Allen picture that dealt romantically — critics might say sentimentally — with the escapes provided by entertainment. Its semi-autobiographical nature is obvious in the way that Allen so lovingly and confidently captures the milieu — a big Jewish family living in Rockaway Beach in the '30s.

 

21. Anything Else (2003)

This was one of Allen's most hated films of the past decade, but unjustly so. While it certainly pillages from the Allen canon (especially Annie Hall), it's not bad when viewed out of that context. Jason Biggs's performance doesn't exactly hide why his career's turned out the way it has, but Christina Ricci is bewitching, and Allen sparkles as the wack-job pseudo-mentor to Biggs. The scene where Allen takes a tire iron to a car windshield is one of the best he's ever performed in. 

 

20. Bananas (1971)

This film is often grouped alongside Love and Death and Sleeper as the best of Woody's "early, funny ones," and while it's the earliest (and weakest) of the three, it still offers up its fair share of laughs, including an absurdist turn by Howard Cosell that, sadly, has severely dated the film. The scene where Woody's guerilla leader orders lunch for his army — "500 grilled cheeses, one with tomato" — is priceless.

 

19. Vicky Cristina Barcelona(2008)

A Woody picture making money! Again! After Match Point's success a few years earlier, this picture's reception made it clear that Allen's European sojourn had resuscitated his career to a degree. Light on the one-liners and heavy on the theatrics, the film could only have worked with hot-blooded performers like Javier Bardem and Penelope Cruz — but it did. It also features a breakout performance from Rebecca Hall.

 

18. Everyone Says I Love You (1996)

Perhaps the last time Woody really pushed himself in terms of genre exploration, this film is a comedy-musical hybrid not unlike the ensemble pictures he loved as a youth. It works better than you might expect, with a surprisingly touching performance of "I'm Through With Love" from the director himself. A few roles do seem miscast — never has Edward Norton been more toothless — but the neurotic Upper West Side Jewish clan is written with zest.

 

17. Hollywood Ending (2002)

One of Allen's most underrated films, Hollywood Ending was reviled when it was released, but the concept is intrinsically funny — a director trying to make a Hollywood film while blind — and Allen runs with it nicely. Treat Williams is excellent as the sleazebag Hollywood producer.

16. Scoop (2006)

If all you want from a late Woody Allen picture is enough laughs to distract you from the void, Scoop delivers. The most recent of Woody's films to feature the master himself performing, it reminds us that no one can spit out Allen's dialogue quite like he can. ("I was raised in the Jewish persuasion," he explains to a group of British aristocrats, "but when I got older I converted to narcissism.")

 

15. Everything You Always Wanted To Know About Sex (But Were Afraid To Ask) (1972)

Anxiety about sex has provided Woody with fodder for laughs for his entire career. But he never exploited it to greater effect than in this picture. Bombastic, wild, the first of Woody' early films to truly have an explosive impact, Everything is as faux-perverse as it is hilarious. Some segments (Gene Wilder falls in love with a goat) don't resonate quite as much as others (sperm preparing to exit the body), but the film made Allen a household name.

 

14. Sleeper (1973)

If Love and Death was Woody's paean to the great screwball movies, Sleeper is his tribute to the silent-era comedies that, while important, left a less obvious influence upon his body of work. Aspects of Charlie Chaplin are clear in the physical comedy of this performance-centric film, set in a futuristic society where Allen has mistakenly wound up. The film has its share of hilarious one-liners, though it would be trumped by its follow-up, Love and Death.

 

13. Zelig (1983)

Back when Woody was ambitious, he made pictures like Zelig, a faux-documentary about a guy with a serious chameleon complex. The title character manages to insert himself into some of the most important moments of his era, often in contradictory roles. Using state-of-the-art technology, Allen was able to insert himself, as Zelig, into newsreel footage from the '20s and '30s. This well-received film is funny and impressive, with a historical flair.

 

12. Broadway Danny Rose (1984)

While it's certainly true that Allen plays the same character in every picture, give or take a bit, there's a little more to his performance as Danny Rose, a sleazebag hapless talent manager who finds himself target of a mob hit. Told in flashback form by a bunch of comedians sitting around the Carnegie Deli, the picture is warm and charming, in addition to featuring one of Woody's most lovable — and asinine — characters.

 

11. Manhattan Murder Mystery (1993)

Perhaps Woody's funniest film of the '90s, Manhattan Murder Mystery saw him reunite with Diane Keaton for the first time since Manhattan, giving her a role initially meant for Mia Farrow. It's a light, breezy picture, but the thriller plot — which involves Allen and Keaton, a married couple, investigating the disappearance of their neighbor's wife — is kept believable enough to build some tension. The film also features some of Woody's strongest lines. ("Claustrophobia and a dead body! This is a neurotic's jackpot!")

 

10. The Purple Rose Of Cairo (1985)

Allen often calls this his favorite of his works, and it's not difficult to see why: the almost fairy-tale narrative setup is married fascinatingly to an utterly cynical, bleak ending that still attempts to find some hope in a hopeless situation. Allen doesn't engage in the fantastic too often, so it's interesting to see him cut loose here with the story of a Depression-era woman whose movie-star crush simply walks off the screen and into real life.

 

9. Husbands And Wives (1992)

One of Woody's most aggressive films both aesthetically and emotionally, this painfully intimate look at the dissolution of two marriages is widely considered to be the last of Allen's golden era that began with Annie Hall. (Indeed, in the nineteen years since, the only truly spectacular films he's made have been Deconstructing Harry and Match Point.) Life soon imitated art, as Woody's relationship with Mia Farrow collapsed when his entanglement with Soon-Yi Previn was revealed.

8. Stardust Memories (1980)

A beautifully shot film that's as abstract and arty as anything Allen's done, Stardust Memories has a dreamy quality that, perhaps surprisingly, complements Woody's comedy quite nicely. With echoes of Bergman and Fellini, the film follows a director being honored at a film festival as he tries to get the various romantic relationships in his life in order.

 

7. Love and Death (1975)

This film probably wouldn't even make the top tens of most critics — too silly, too early, too loose when compared with the works of Woody's "serious" period — but it makes me laugh harder and more often than almost any other film I've ever seen. The pinnacle of Woody's early period, Love and Death is a Russian tragedy spoof that's thick with sharp one-liners. "Boris Kruschenkov, you are the greatest lover I have ever had," the beautiful Countess informs Boris (Woody) after a bout of lovemaking. "Well," Boris replies, "I practice a lot when I'm alone."

 

6. Deconstructing Harry (1997)

The major highlight in the otherwise creatively difficult period that ran from Husbands and Wives to Match Point, Deconstructing Harry is a bitter self-critique about a novelist who pillages his personal life for the sake of his work — and continually incurs his friends' ire for it. The basics of the plot recall Bergman's Wild Strawberries, with the key difference being that Bergman didn't intersperse his picture with scenes of his protagonist discussing prostitutes' blowjob skills with the devil. Comedic interludes like that one are presented as scenes from our protagonist's books, but they play out like stuff from Woody's early career, only darker. Perhaps one of Woody's most personal films, Harry certainly has a sting to it.

 

5. Hannah and Her Sisters (1986)

Allen's films often involve ensemble casts, but in no film did he work the ensemble better than here, with branches of a family intersecting and diverging like vines. It's perhaps Allen's most humanist film, reasserting the importance of perseverance in the face of adversity. Woody, as a hypochondriac who may actually have a dangerous illness, is particularly touching, and his first date with Dianne Wiest is one of the funniest scenes he's put on film. The ending, in which everything is wrapped up neatly and happily, feels a bit forced, and Allen himself acknowledged as much, saying that the ending of Crimes and Misdemeanors was his attempt to rework the end of Hannah, wherein he "let the characters off too easily."

 

4. Crimes and Misdemeanors (1989)

In a delicate balancing act, Woody weaves the tragic story of an ophthalmologist who has his mistress murdered with the comedic tale of a documentary filmmaker's battle of wits with his brother-in-law. The twist is that the filmmaker (Woody, of course) is making a documentary about a Holocaust-surviving philosopher (modeled after Primo Levi) whose insights into the human condition explain the decisions made by the aforementioned ophthalmologist. With its stance that the universe is a morally bankrupt place where we must supply our own meaning — and that even doing that doesn't grant us salvation — this is Allen's most ethically rich film.

 

3. Match Point (2005)

An improvement upon Crimes and Misdemeanors in that the murder in C&M is one of necessity, when in Match Point it's absolutely one of choice. In the earlier film, Judah risks going to jail if he defies his mistress, but our protagonist here risks only having to find a new job. Yet to Jonathan Rhys-Meyers' ambitious social climber, the lure of the good life is simply irresistible. By slightly changing the framework of his previous classic, Allen was able to even better depict the lengths we go to to preserve the realities we've constructed for ourselves.

 

2. Manhattan (1979)

The apex of Allen's eight-film collaboration with cinematographer Gordon Willis, Manhattan remains the most aesthetically ambitious work in Woody's oeuvre. Shots like the now-famous image of Woody and Diane Keaton looking at the 59th Street Bridge are a reminder of how much dialogue-heavy films like Allen's need a strong visual identity to balance them out. Beyond the superb camerawork, the film marks Allen's first (and most sincere, naïve, and endearing) engagement with personal ethics. The "you'd rather buy the Porsche" speech about integrity is as unforgettable as that moment by the bridge. It's extremely difficult to deal with such issues head-on in cinema, but the humor and cadence of Allen's dialogue makes the film's big themes quite moving.

 

1. Annie Hall (1977)

What's most incredible about Allen's greatest work — one of the greatest American films ever made — is how natural the stream-of-consciousness narrative structure feels. It takes about ten viewings before you begin to remember which scene follows which, because the cutting serves the workings of memory and characters' associations rather than any linear chronology. It's an experimental film that no one realized was experimental. Of course, structure aside, this film still remains the depiction of how relationships do — and do not — work in the modern era. Effectively the turning point in a career that was moving from zany comedy to dark existentialist drama, this film perfectly blended Allen's absurd humor with his dark take on human nature, by providing the insight that our most irrational needs are often our most strongly felt ones — as evidenced by the joke ("I would, but I need the eggs") that ends the film.