Ranked: All 50 Woody Allen Films From Worst to Best

American Masters

Woody Allen is my favorite filmmaker. Full stop. There are dozens tied for second place, but he's the one on top. I love his comedies, I love his dramas and I especially love when the two drift into one another.

If a clip from a lesser-loved Woody Allen movie comes on and someone rightly asks “who lives like that?” I answer, “people in Woody Allen movies do, that's who.” My emotional life remains fairly stable; I can live precariously through the tortured artists and the poisoned relationships of the higher tax-bracketed, as seen in (most of) his films. I love the Allen persona and I love the way he writes for women. I love the people with whom he collaborates – groundbreaking cinematographers like Gordon Willis and Darius Khondji, as well as his go-to production designer Santo Loquasto and costumer Jeffrey Kurland.

Then there are also the zings. While the Woody Allen screen persona has remained somewhat frozen in time for fifty years (50% neurotic Eisenhower-era enriched New York City Jew, 25% Bob Hope letch, 20% Groucho Marx wiseacre, 5% Chaplin-esque imp prone to sight-gag foibles, though my math could be a tad off) the writing still remains fresh. And the Woody persona will be one of the lasting icons of our time. (Few remember that, for eight years, King Features ran a licensed comic strip called “Inside Woody Allen.”)

Woody Allen has directed fewer than 50 films, but he's been involved with many more. To rank them all and reach a cool 50 titles, (and to figure out where this week's release “Blue Jasmine” fits in) I came up with a special game plan.


1.) Anything Woody Allen wrote or directed HAS to be on the list. (Woody didn't direct “Play It Again, Sam,” but he wrote it, starred in it and the successful Broadway production was key to cementing his persona. It qualifies.)

2.) Anything Woody Allen starred in, but did not write or direct, CAN be on the list if it merits it. (In other words, you'll be reading about Martin Ritt's “The Front,” a Rollins-Joffe production, because it is good. Not so much on Alfonso Arau's “Picking up the Pieces” (2000), Paul Mazursky's “Scenes From A Mall” (1991) or the TV production of Neil Simon's “The Sunshine Boys” (1997) opposite Peter Falk, even though one of 'em - “Mall” - is certainly better than #50 on this list.)

3 .) Cameos don't count. (Sorry Doug McGrath's “Company Man” (2001), Stanley Tucci's “The Imposters (1998) and Jean-Luc Godard's “King Lear” (1987). All three of you are more interesting that the #50 pick on this list, but let's be frank, you aren't Woody Allen films.)

If you disagree with this criteria I politely invite you to pull Marshall McLuhan out from behind a placard to tell me my whole fallacy is wrong. Here we go.

50 – "What's New Pussycat" (1965)

The movie that took Woody Allen out of the Greenwich Village nightclubs and off the Tonight Show couch is something of a milestone – but it's also absolutely awful. I hated it as a kid when I was first discovering Woody's back catalogue and I hated it last week when I revisited it for this list.

Peter O'Toole plays a British playboy who wants to be faithful to his German fiancee (Romy Schneider), but who can resist when every European sexpot keeps throwing themselves at your feet? (Ursula Andress literally falls out of the sky wearing some kind of leopardskin zip-up number.) There are some amusing moments with a badly wigged Peter Sellers as O'Toole's shrink Dr. Fritz Fassbender and Woody doing very early schtick as Victor Shakapopulis, but it doesn't cut above the cacophony of an aggressively poorly made and annoying picture. Here's the thing, though: it was a crazy success (yes, it's got the Tom Jones song and everything) but Woody hated it. It inspired him to say “never again!” to taking a mere screenwriting job. From here on in, he would direct his own work, so, in a way, we owe the rest of this list to the horridness of this film.

49 - "You Will Meet a Tall Dark Stranger" (2010)

There are a lot of people who want to tell you that Woody has been on autopilot since “Deconstructing Harry.” These people are cretins. It is true, however, that Woody's style of directing is a little. . .unusual. He trusts his casting instincts and will really only give any guidance to performers if they ask for it or if he feels they are doing something wrong. He shoots in long, wide takes and there are times when a little conventional coverage may, yes, help tighten the scene. The fact that Woody has publicized that he likes to shoot quickly so he can be home for dinner or to catch a Knicks game doesn't do him any favors.

Nevertheless, I refuse to call Woody, even the later Woody, a sloppy filmmaker. Except for this one. It has no life. And it really feels like a retread. Another story of frustrated artists and wealthy people making one another miserable, set in England only because that's where the money happened to come from. I came out of this one almost convinced that maybe Woody should retire. Of course, he followed this up with “Midnight in Paris,” so what do I know?

48 - "Alice" (1990)

Okay, from here on in, every movie on this list is worth checking out. Though we're still in a zone where I'm hesitant to jump up and down and call these titles superb.

In “Alice,” Mia Farrow plays a sheltered, rich Park Avenue wife. A trip “down the rabbit hole” of extra marital flirting leads to her reevaluate her life and her goals. The tone is light and the scenes all feel a little worn. Quite frankly, the lazy qualities some ascribe to Woody's later films first presented themselves with this one. There's a “magical realism” element in this one that's a bit half-baked, and I don't quite buy Joe Mantegna as a jazz-bo. Still, some fun moments and the location photography of “Woody's New York” is still in its prime.

47 - "Cassandra's Dream" (2007)

Perhaps my medium-low opinion of “Cassandra's Dream” comes as a result of its timing. Woody had recently come off of “Match Point,” a sharp morality tale set in London. “Cassandra's Dream” is, to a large extent, a reprise of similar themes. Is it right to kill a random person to get yourself out of a jam? No, of course not, but could you do it? Well, some yes and some no. Is there any sort of justice? Well, it depends on if you consider bad luck justice. And so on. It's big fat Russian novel stuff and it's just been done better. While the Philip Glass original score is moving (and the British dialogue feels sincere,) you are better off sticking with Scarlett Johansson in “Match Point.”

46 - "The Curse of the Jade Scorpion" (2001)

This list's first point of controversy! How could I possible place this dud above the somewhat-similar magic-rich “Alice?” Well there are two things I really like about this lesser-Woody picture. One, the 1940s design and overall look is top notch (this was one of three films shot by Chinese DP Zhao Fei.) Two, David Ogden Stiers plays the heavy, a criminal mastermind / hypnotist named Voltan. How can you not love that?

Third and most importantly, it's wonderful to see Woody play with genre. Granted, this movie is something of a tossed-together enterprise, but when you have a CV like Allen has you can allow yourself such indulgences. To see him cast himself as a screwball private eye (and with Helen Hunt as his Rosalind Russell sidekick) is to see a guy having a good time. Inasmuch as anyone who plays the eternal schlemiel can have good time.

45 - "Scoop" (2006)

More magicians, more murder, more England. But, this time, Scarlett Johansson in a red bathing suit!

There are some solid zings in “Scoop” but this is light as meringue and there are some who don't really buy the beautiful Johansson as a clumsy doofus. (I'm on board with whatever she brings. Did I mention the bathing suit?) It's also funny that this entire movie is, in a way, based off of a throwaway gag from “Broadway Danny Rose.” Still, Woody Allen as “The Great Splendini,” a low-rate prestidigitator living in the UK for some reason (and having to sleuth around stately manners) is, indeed, funny.

44 - "Melinda and Melinda" (2004)

This one makes me feel a little guilty, because I want to like it more. It's a solid idea, but doesn't quite crystalize, a little ironic as it is about the craft of storytelling.

Wallace Shawn and, as it happens, two of his costars from Louis Malle's “Vanya on 42nd Street” are having a late dinner at Pastis in the Meatpacking District. (2004 on film!) They are discussing an event that happened to a friend of a friend and soon dueling versions of the story are created. One is a comedy, the other tragedy. We now shift between the two, which rhyme with one another in clever ways, but what we're ultimately left with are two halfway interesting stories.

One has to wonder if Woody himself had a flash of an opening scene, didn't know whether to go smiles or tears and said “eh, let's try both.” Despite some funny moments (Will Ferrell does well as the Woody persona stand-in) and decent performances (Radha Mitchell in the double role, plus a very agreeable Chiwetel Ejiofor) “Melinda and Melinda” is, unfortunately, more “interesting” than good.

43 - "To Rome with Love" (2012)

Coming off of the success that was “Midnight in Paris,” Woody kept that grand European tour going and went to Rome. The results, unfortunately, are mixed.

Four short films that, really, have absolutely have nothing to do with one another are scrambled together with a epilogue consisting of a crane shot and somebody saying “Roma!”

The section of Alec Baldwin advising his younger self (kinda) in the matters of love has the most heart, but Ellen Page doesn't quite work as the voracious cauldron of seduction the screenplay calls for. Roberto Begnini (remember that guy?) is amusing as the common man suddenly thrust into celebrity. Woody himself shows up as a failed opera impresario who happens upon his diamond in the rough (or, in the shower.) There's a fourth section not even worth discussing. The whole thing is amusing, but certainly a letdown after “Paris.”

42 - "September" (1987)

From 1983 to 1987 Woody Allen pumped out five masterpieces in a row. This didn't exactly come to a screeching halt with “September,” but it definitely hit a minor speed bump.

Steeped in Anton Chekov, this end-of-summer drama set at a country house is somewhat reminiscent of Woody's earlier (and very misunderstood) "Interiors." Partially, because it is all shot in interiors! Mia Farrow is recovering from a suicide attempt and this "filmed play" is a heavy final weekend with her best friend (Dianne Wiest) and mother (Elaine Stritch). Neighbors Sam Waterston (a struggling writer, naturally) and Denholm Elliot (a disillusioned intellectual) pop by, as does stepdad Jack Warden, a physicist with the film's best monologue. Everyone is in love with everyone else, they all have secrets and the whole thing is a real quiet bummer.

The most noteworthy thing about this film is something that happened off-screen. Somewhere out there is an ashcan version of "September." Woody shot the whole thing with other actors - Sam Shepherd, Charles Durning and, most interestingly, Maureen O'Sullivan, Mia Farrow's actual mother, in the mother role. (Interestingly, O'Sullivan had just played Farrow's mother in "Hannah and Her Sisters" quite to great acclaim.)

Well, Woody didn't like what he saw and and re-did it soup-to-nuts. I can't think of another example of this happening in film history. Andrei Tarkovsky had to reshoot "Stalker" because of a film lab screwup, but this was by choice. And those tortured artists in Woody's films are make believe, huh?

41 - "Everything You Always Wanted to Know About Sex * But Were Afraid to Ask" (1972)

We've left the slightly wobbly zone and now we're airborne. Everything from here on in is essential to some degree. "Everything You Always Wanted to Know About Sex * But Were Afraid to Ask" is a great sample set of the "early, funny ones," a collection of dopey sketches that promise perversion and bring laughs.

The best bit is the last one, in which Woody Allen plays a sperm and Tony Randall is mission control in a man's brain. As soon as he hears his date is a graduate of NYU he shouts "we're in!" There's also a section that's a wonderful parody of Antonioni-esque Italian cinema. If you've ever seen a pic of Woody in hip shades smoking a cigarette, it is from that segment.

40 – "Antz" (1998)

Remember "Antz?" Maybe you do. It was the "Olympus Has Fallen" to "A Bugs' Life"'s "White House Down." Also: a hundred times better.

Written by Paul and Chris Weitz and playwright/performance artist/blogger Todd Alcott, "Antz" is an adorable story in which a Woody Allen ant has to face his fears with the help of his best pal, Sylvester Stallone ant. Christopher Walken ant is the bad guy. Bad ant.

Anyway, there are a lot of zings that are fun for the whole family and what's best is that it 100% utilizes the Woody Allen persona. This is a great gateway drug for little kids to get into the neurotic, self-deprecating humor of the world's greatest filmmaker!

39 - "What's Up, Tiger Lily?" (1966)

Something of a deep cut, this post-"What's New Pussycat" project is one of the stranger entries on the list. Woody took the none-too-spectacular chop-socky import "International Secret Police: Key of Keys" and dubbed in his own ridiculous dialogue. As such a spy picture was transformed into quest to find the secret recipe for the world's greatest egg salad. As a bombshell dame disrobes she seductively demands "name three presidents!" It's wall-to-wall absurdism with some non-sequitir musical numbers from period band The Lovin' Spoonful (one of the few interactions between Woody, a jazz and standards connoisseur, and the less-refined world of rock.) Lovers of "Mystery Science Theater 3000" have an obligation to seek out this gem.

For crazy 60s Woody, this is also a better bet than trudging through the original 1967 "Casino Royale." While Woody's few scenes are funny (as are the bits Terry Southern contributed) that Frankenfilm with six different directors is best approached in its own context.

38 - "A Midsummer Night's Sex Comedy" (1982)

"We can't have intercourse where we eat our oatmeal!"

It's one of hundreds of thrown-away Woody Allen lines but this one, for whatever reason, is one of my favorites. It's another story of wealthy, fascinating people having romantic misunderstandings in a charming location, but the hook here is the early 20th century setting. Woody plays a wacky inventor and Jose Ferrer is a noted philosopher. Mia Farrow is once again the center of attention and Julie Hagerty - yes, the woman from "Airplane!" - gives a solid performance, too. God knows why she never caught on, she's pretty good in this. Despite the Shakespearean title, there's more in common here with Bergmans “Smiles of a Summer Night.”

37 - "Anything Else" (2003)

When this came out I saw it and shrugged it off as another decent-enough late-era Woody film. Then Quentin Tarantino bafflingly included it on his list of the twenty best films of modern times. I'll admit, his voucher got me to reevaluate this one, and while I still think he's a little nuts, I do see that there's some interesting stuff going on here.

Jason Biggs (!) is a young nudnick-y comedy writer at an emotional and professional crossroads. Woody's character Dobel is a possible older version of himself - angry, paranoid and not particularly accomplished. "Anything Else" is one of Woody's few films to directly address a post-9/11 state-of-mind, and there are interjections from Biggs' in-progress book that have a Godard-ian effect. You, too, should see this one again.

36 - "Small Time Crooks" (2000)

Clumsy, low-rent Woody Allen as a safecracker, shrill Tracy Ullman as his wife and "dumb as a horse" Elaine May for added punchlines. Listen, anything with Elaine May in it should be treasured like gold, but her flummoxed, speech-impeded cluelessness really makes this picture. The mid-story twist is when this strictly walk-up apartment gang strike it rich not through crime but by the success of their baked-goods front operation. The perennially dissatisfied Woody character is miserable as an uptown swell - all he ever wanted was to retire somewhere warm enough to go swimming.

35 - "Celebrity" (1998)

Next time you hear Beethoven's Fifth you can say, "Oh, that's the theme from Woody Allen's 'Celebrity!'"

Kenneth Branagh stars as the disaffected writer stuck taking cheap assignments, and the only actor who decided that playing the Woody surrogate role meant he should do a Rich Little-style impression. Shot in Black and White and featuring small roles from Leonardo DiCaprio, Melanie Griffith, Bebe Neuwirth, Isaac Mizrahi, Donald Trump, basketball star Anthony Mason and film director Greg Motolla, "Celebrity" isn't quite the bile-informed takedown of paparazzi and tabloid culture you'd expect from a guy who was a constant salacious headline for a year. It's another riff on the woes and aspirations of New York's elite, but set in a slightly different context.

34 - "Don't Drink the Water" (1994)

First a play, then a so-so film starring Jackie Mason and then, finally, a forgotten made-for-TV picture from the mid-90s. Here's the thing: it's hilarious.

Michael J. Fox is a frazzled US ambassador of “Vulgaria” and Woody is the patriarch of a trapped Jewish family on vacation. Julie Kavner (yes, Marge Simpson) is his always right but always nagging wife and Mayim Bialik is the daughter/love interest. Dom DeLuise shows up as a priest. Yeah, I know - you are wondering how the hell you've never seen this.

The zings are nonstop, especially when an Arab sheik and his harem of wives enter the mix. "How does he ever get time in the bathroom?" is the question only Woody Allen would think to ask.

33 - "The Front" (1976)

The first and, for many years, only acting gig Woody took after he'd been firmly established as a filmmaker. This was the first major movie to discuss the Hollywood blacklist, featuring many actors whose fellow traveler status cost them their livelihoods during the McCarthy period.

"The Front" plays off the side of Woody's streetwise everyman persona, not the melancholy intellectual. He's a cashier at a diner (and occasional numbers runner) who happens to know a bunch of comedy writers who need a fresh face that can present their work. In addition to exposing this odd chapter of American political history there's some wonderful firsthand insight into the production process of live TV during its "golden age" and a heartbreaking performance by Zero Mostel.

32 - "Whatever Works" (2009)

Part of loving Woody Allen is loving that he can be a little clueless about modern times. He's a classicist, an old soul and a genius, so he has a right to think that freewheelin' bohemianism is still par for the course down in Greenwich Village in 2009. (It is, in reality, a section of town thoroughly overrun by corporate NYU and million dollar apartments.) "Whatever Works" was an old script Woody had laying around, originally intended for Zero Mostel, that barely had the cobwebs blown off of it before handed to Larry David to star.

Still, David makes a solid Woody proxy, griping about life's indignities and wandering around Central Park in a pair of brown shorts. David's own persona bleeds into the character a bit and it is a welcome addition. Here is a man whose sole desire is just to be left the hell alone, but can't help meddling in the affairs of a Southern Belle who literally steps off the bus and into his life.

31 - "Wild Man Blues" (1997)

Horrible working conditions in an Appalachian coal mine. Protracted labor struggles in the American heartland. Woody Allen's dilettantish Dixieland jazz band on a concert tour? One of these things is not like the other, but all are remarkable documentaries by Barbara Kopple.

Everyone knows that Woody is a good-but-not-great clarinetist, but few can make it to his semi-regular uptown club engagement. In a wise marketing move after years of tabloid coverage, Woody allowed (hired?) Kopple to shoot as he marched through the great nations of Europe with his rather plain wife Soon-Yi Previn and protective sister/producing partner Letty Aronson. This is the closest we'll ever get to seeing what Woody is really like, and the answer is: not that dazzling. But interesting and still funny. The reward at the end is a trip to his none-too-impressed parents. Amidst the discarded Oscars in the nonagenarians' apartment Woody's Dad misreads an Italian plaque reading "Grazie, Woody" as "Crazy Woody," and Mom shuts down the film with an all-too-perfect "enough!"

30 - "Vicky Cristina Barcelona" (2008)

If you are going to kick back and enjoy the lives of tortured romantic souls, it doesn't hurt that they look like Scarlett Johansson, Javier Bardem, Rebecca Hall and Penelope Cruz. And it also doesn't hurt to set the movie in Barcelona. There's passion and arguing and big, beautiful paintings and lots of drinking wine outdoors. This among the better examples of Woody's knack of taking what would be pure soap opera - a "chick flick," if I may use that ludicrous phrase - and elevating it to something else. There's no Allen persona proxy here - this a romantic drama whose gorgeous setting, nuanced characters with relatable aspirations and crisp dialogue make it palatable for those of us who'd twitch at the mere thought of watching the Lifetime Network.

29 - "Match Point" (2005)

Among the most nihilistic film on this list, "Match Point" is a "Crime and Punishment" riff set in London high society which proved that Woody's trademark style was something of a movable feast. It was his first London film - a business concession - but the verdict was clear. Despite Woody's love and devotion to New York, the spark was in him and not the locations.

As for the story, Jonathan Rhys Meyers is a rampaging id - a conniving, murderous social climber that somehow remains sympathetic. With the lights dimmed we are confronted with the fact that inside of us all is a wretched creature who will do any horrible act to capture and retain what we desire - especially if we don't get caught. Luckily, most of us don't act on the impulse.

Also, if I may: Scarlett Johansson, blue jeans, the rain. Thanks for that one, "Match Point."

28 - "Sweet and Lowdown" (1999)

"You love jazz!" said one of the idiot producers in "Stardust Memories." He wasn't just whistlin' dixieland. While we twiddle our thumbs in anticipation of a Django Reinhardt biopic (dude lived a crazy life) we'll have to settle on this film in which the noted gypsy guitar player is merely idolized by its talented-but-flawed lead character.

Sean Penn's Emmet Ray is presented as a tall tale with fake interviews sprinkled in (can I get a what-what for Nat Hentoff? Nat Hentoff in the hizzouse!) and his career is romanticized in loving fashion. His romance with mute Samantha Morton is something of a nod to Fellini's "La Strada," but Ray isn't a strong man with a heart of gold - he's an egoist with a heart of fragile glass. Woody's longtime collaboration with composer Dick Hyman reaches its natural apogee here.

27 - "Midnight in Paris" (2011)

Tourism bureaus in every nation got the message - invite Woody Allen shoot there. (Alas, "To Rome With Love" wasn't quite the follow up Italy was expecting, but points for trying.)

Woody's love letter to Paris, romance and day dreams is ridiculously watchable, and this became the biggest financial success of Woody's career. It's roots are the simple fantasy experiments found in his New Yorker short stories like "The Kugelmass Episode." The Allen proxy (Owen Wilson) is a frustrated writer who is transported back to the parties and company of the Lost Generation. While there he meets the love of his life (Marion Cotillard) who, naturally, is equally disaffected and longs for La Belle Époque. Well, wherever you go, there you are. Bonus points for a joke that means nothing if you aren't up on your Bunuel.

26 - "Hollywood Ending" (2002)

Leave your scathing comments below. No, this isn't a formatting error. Yes, I am purposely placing this much maligned film this high on the list. It's funny. It's really funny. The scene where Woody flips out at Tea Leoni in the restaurant is fantastic. Every dopey moment when Woody, secretly suffering from hysterical blindness on a movie set, makes some dumbass and predictable joke kills me. Woody's revelatory punchline of "it looks like a blind man made this!" knocked me out of my chair with laughter and the added cherry of him becoming a hit in France destroyed me. Maybe I'm the only one but I love this idiotic movie.


25 - "Bullets Over Broadway" (1994)

Years before "Analyze This" Woody turned in this sharp mob comedy that is among the funniest on this list in which he does not appear. John Cusack wants to be a pure artist, but to get his plays funded he needs to make concessions. It means letting Jennifer Tilly, a backer's girlfriend, in the cast. It also means taking script notes from her bodyguard (Chazz Palminteri) who actually has a knack for storytelling. Dianne Wiest is at her finest as the histrionic grand dame and Rob Reiner (yay for onscreen Meathead!) is fantastic as the allegedly conscientious intellectual.

To young people reading this: there was once a time, a pre-Sarah Silverman time, as recently as 1994 when the word "vagina" was something that you rarely heard outside of a science class. Wiest's use of it as a punchline in this was . . .well, not quite shocking, but certainly sharply original. I was lucky enough to see this in theaters more than once and you should have heard the reaction.

24 - "Interiors" (1978)

People were not ready for this movie. There were even jokes in MAD Magazine about this movie, presenting it as a misstep. Everyone was wrong - this movie, albeit an Ingmar Bergman "homage" to a near-litigious point - is fantastic.

Marvelously shot by Gordon Willis (at "Klute"/"The Parallax View" levels of sublime framing), this intense story of a miserable, wealthy family is as psychologically profound as it is soap opera juicy. Patriarch E.G. Marshall decides that, with the three daughters grown, he's leaving his emotionally unstable wife. This sets off a major chain reaction that culminates in fireworks at his marriage to his new wife, a never better Maureen Stapleton (the only one in the movie not wearing drab earth tones.)

Steeped in hardcore 70s tropes (the eyeglasses! the politics! the pedantic discussion!) this movie somehow retains the uncanny knack of making the lives of these extremely unhappy people seem enviable. Though maybe it's just me.

23- "Blue Jasmine" (2013)

"Blue Jasmine" is a shocking break from tradition. In it, New York City is the bad guy.

In another world the scenes set in San Francisco might have just been "downtown" or Queens, so I won't read too much into this. Besides, there's a lot else to focus on, primarily the remarkable lead performance by Cate Blanchett.

As a slightly more subtle (or less comic) variation of a Judy Davis neurotic, Blanchett's Jasmine is fallout from headline's footnote - a suddenly impoverished Park Avenue adult baby trying to figure out how to survive among normal people. Clutching her Hermes purse like a security blanket (and flashing back to her life with Bernie Madoff-esque Alec Baldwin) Blanchett's fall from grace is a remarkable mix of sympathy and schadenfreude. The next time you see someone talking to themselves at the park you'll think of her.

Read our full review here.

22 - "Take the Money and Run" (1969)

Woody Allen's first real movie. A hilarious mock-documentary about an alleged criminal mastermind that features one of Woody's all-time classic bits, trying to hold up a bank but having such bad penmanship no one can read his threatening note. ("It doesn't say 'gub' it says 'gun!') Once captured, Woody sings work songs on a southern chain gang and his parents, as interview subjects, wear Groucho glasses to hide their identity. Additional insanity comes when he tries to break out of prison by creating a fake gun out of soap and shoe polish, which doesn't go so well when it turns to bubbles in the rain. Also - "Take The Money And Run" finally answers the question "how does one play the cello in a marching band?" Funny, dare I say zany stuff.

21 - "Manhattan Murder Mystery" (1993)

After Woody's tabloid drama of 1992 he decided to go back to the well of his old co-writer Marshall Brickman and best on-screen comedy partner Diane Keaton. Fleshing out a chunk of the original, discarded script of "Annie Hall," the result is wall-to-wall laughs, a feel-good romp like he hadn't done in years.

It's really just a framework for non-stop zings and even some physical comedy, but this paranoid caper (with nods to Orson Welles' "The Lady From Shanghai") offers a view at a specific New York peculiarity - how you can live inches away from someone in an apartment building but have absolutely no idea what they are actually like. Bonus points for casting Anjelica Huston and Alan Alda as the friend couple.

20 - "Play It Again, Sam" (1972)

Woody Allen did not direct this one (Herbert Ross of "The Sunshine Boys" and "Footloose" did) but "Play It Again, Sam," based on Woody's successful play, was a key block in building the "intellectual Woody" persona. As Allan Felix, he plays a dreamer film critic (!) that's a loser to some, but an enlightened romantic to others.

While Ross does a good job opening the script up (the film was moved to San Francisco due to a strike in New York) the dialogue is the star. Woody's banter with Diane Keaton (and an imaginary Humphrey Bogart) are rock solid and the "Casablanca"-esque ending suggests many of the magical realism moments in films yet to come.

19 - "New York Stories" (segment "Oedipus Wrecks") (1989)

A short film? Wait, does that count? When it's as hilarious as this one, for God's sake, YES!

For all of the "Jewish humor" in Woody's films there isn't that much dealing with the typical overbearing mother. So he goes all-in on this one. A trip to a magic show goes wrong (reminiscent of "Scoop" and "Broadway Danny Rose") and Woody's nurturer/torturer somehow ends up hovering over Manhattan, humiliating her son in front of the entire city.

It's a wonderfully funny piece and it ends with a loving dollop of schmaltz dripping from Julie Kavner's boiled chicken as the physical representation of happiness. “Oedipus Wrecks” comes bundled with Martin Scorsese's outstanding SoHo artists' time capsule “Life Lessons” written by Richard Price and Francis Ford Coppola's frequently maligned but not wholly without virtue “Life Without Zoe” written by a still green Sofia.

18 - "Another Woman" (1988)

"I accept your condemnation."

Ian Holm's cold and supercilious catchphrase is one of the most brilliant moments of passive-aggressive behavior ever caught on film.

Gena Rowlands plays the uptown woman of means whose voyage of self-discovery begins when she discovers a new apartment allows her to eavesdrop on the therapy sessions of (aha!) another woman. Mia Farrow's frustrations and self-doubt starts to bleed into her own life, leading to some shocking revelations. Is ignorance bliss? Is there any point in wondering about the road not taken? When looked at this way it isn't too dissimilar from “Alice,” but with a much more serious tone.

Like "Interiors," "Another Woman" has a strong Ingmar Bergman vibe, in this case a gender-swapped riff on "Wild Strawberries." This is also the only Woody Allen movie I can think of that uses dream sequences in a serious context, not as a goof (e.g. parallel parking crucifixes from "Bananas.")

17 - "Everyone Says I Love You" (1996)

We're now in the zone where each of these films are more than great, they are fantastic. Seeing every one of these is non-negotiable in my book.

In “Everyone Says I Love You” Woody's love of the Great American Songbook comes to its logical conclusion. This is an effervescent musical-comedy in the grand 1930s tradition. An enormous (and enormously wealthy) family put the affairs of the heart to tunes from old movies. "Hooray For Captain Spaulding" is sung by a room full of French people in Groucho glasses. Why are you not watching this right now?

Of the many charming moments, highlights include Alan Alda as the limousine liberal head of the household, young Natalie Portman giggling on Manhattan's Upper East Side, Julia Roberts succumbing to Woody's sexual technique and one of the greatest/dumbest jokes ever: when Woody's daughter (Natasha Lyonne) says she's in love with a gondolier, Woody retorts "you know what rhymes with 'gondolier?' No Lire!"

Okay, it's a lot funnier when you hear him say it. Anyway, if you don't get the chills when Woody and Goldie Hawn dance along the banks of the Seine you are not human.

16 - "Mighty Aphrodite" (1995)

At night when it is just me and my thoughts I fantasize about a world wherein F. Murray Abraham leads a (literal) Greek chorus commenting on my life.

Woody Allen and Helena Bonham Carter adopt a child and, perhaps reasonably, Woody recognizes that some day the boy will try and seek out his biological mother. After some snooping he discovers Mira Sorvino, a foul-mouthed prostitute, but luckily one with a heart of gold. Woody's attempts to try and set her life on the “right” path is one comic scenario after another. Sorvino rightly won the Oscar for this. A lesser actress could have said the shocking jokes just as well, but her lurid talk comes couched in an ineffable purity. It's a touching, odd duck performance.

15 - "Husbands and Wives" (1992)

I remember reading a review – I wish I could remember from whom – that said we'd need a great deal of time to process “Husbands and Wives” outside of the very public scandal that broke just as the film was released. I guess that means now.

A movie in which Woody Allen and Mia Farrow suffer a painful breakup (and in which he is drawn to a barely legal girl) was bound to get the People Magazine set's heads to explode. But gossip aside, this is a mesmerizing film with outstanding performances and an unusually muscular, hand-held and mobile shooting style.

With a foot in mock-documentary, Woody, Mia, Liam Neeson, Sydney Pollack, Juliette Lewis and especially Judy Davis offer up some of their best work as crisis-prone lovers caught up in unhappiness and deceit. Reminiscent of Bergman's “Scenes From A Marriage” (but definitely a little more droll) “Husbands and Wives” is uncomfortable and unsettling, but only the extremely lucky will find themselves unable to identify with one of the warring parties at some point. The movie does end with a full-blown condemnation of Mia Farrow's character – perhaps a little unfair at the time, but now, with time, we can read it strictly as fiction.

14 - "Crimes and Misdemeanors" (1989)

For a movie with a lot of laughs, this one is really depressing.

Multiple storylines converge to prove that there is no such thing as justice, rightful guilt can be assuaged by time and nice guys finish last (or, in Sam Waterston's case, blind.) “God is a luxury I can't afford,” states Martin Landau, a patrician philanderer who'd rather have his ready-to-squeal mistress murdered rather than rattle the cage of his comfortable life. Somehow, through the miracle of cinema, he is (somewhat) sympathetic. Woody's character leads a B-story of a struggling documentarian whose life's work about a professor and Holocaust survivor kills himself, thus negating his humanist philosophy and spoiling Woody's film. He takes a paycheck job profiling a hack TV producer played by Alan Alda, but spikes the gig by splicing in footage of Mussolini.

The Landau story, however, is almost the most nihilistic thing put to film. A last-minute bit of dialogue from Waterston saves it, or else they would have had to've served cyanide at theater concession stands. Bonus snobbery points, as this is the only movie that makes a Schubert vs. Schumann joke.

13 - "Shadows and Fog" (1991)

Another controversial pick! Now, perhaps this one is getting a boost from the setting in which I saw it. I was young, I knew I would soon be off to study film in college. I saw it at the “artsy” movie theater (in Red Bank, New Jersey) with one of my first real girlfriends. (And my parents, because I didn't drive. But we at least sat in a different row.)

Add to this that I was self-educating myself on the classics of early cinema, which included German Expressionism, and I was reading Kafka and I was enough of a Woody freak that I'd read the one-act play “Death” from which this film was developed. “Shadows and Fog” was also something of a financial flop, proving even more so that it was brilliant!

Anyway, this dreamlike pastiche of European dread and carnival tropes can stand on its own feet, not just my personal nostalgia. Also, if you wanted to link Madonna and Wallace Shawn in the Kevin Bacon game, this is the one that does it.

12 - "Bananas" (1971)

When the phrase “the early, funny ones” comes up, this is arguably the most popular of that group. “Bananas”' wafer thin plot about a products tester (Fielding Mellish, the greatest of the Woody persona names) who somehow ends up leading a Latin American revolution. The film opens with Howard Cosell hosting a live telecast of a political assassination, a pretty out-there concept for 1971. The film nicely bookends with Cosell giving the play by play of Allen and Louise Lasser on their honeymoon night.

In between are some of Woody's most famous and goofy bits, like being harassed by a young Sylvester Stallone on the subway and being publicly humiliated for buying pornography. (“How much for a copy of Orgasm Magazine?!? This man wants like to buy a copy!!!”) Woody's love for the Marx Brothers isn't just felt in the title (“The Coconuts” anyone?) but in a drawn out courtroom scene that tries to rival the one in “Duck Soup.” Tries, but fails. Woody would agree with me there.

11 - "Deconstructing Harry" (1997)

To be a truly successful writer, many believe, you have to be a bit of an asshole. Woody's Harry Block is a darker version of himself – an author who plunders the private moments of his life and all those around him for his books. Anyone caught up in his life will eventually be exploited, but, as is ultimately revealed, it is worth it because only art is controllable. Life is too messy.

This may sound a little heavy, but it's hysterical. The film jumps between reality and fiction (including a number of short sketches – no doubt half-baked ideas in Woody's famous writing desk drawer that could never be developed into larger pieces.) In addition to a really strong performance by Woody himself there are some outstanding moments from Judy Davis, Eric Bogosian, Bob Balaban, Richard Benjamin and even Billy Crystal. Kirstie Alley has a histrionic moment that is, without question, the best thing she ever did in her career.

Anecdote: I saw “Deconstructing Harry” in the theater multiple times. During one mostly empty matinee at the Loews on 19th Street and Broadway there was a man sitting alone in the back row howling with laughter. Not just howling, screaming. Literally bellowing at full voice “ahhhhhhhhhh!” at the screen. It wasn't a put-on, he was someone in the throes of absolute bliss, just overwhelmed by comedy and the physical effects of pure, fiery laughter. During the aforementioned Kirstie Alley bit I honestly thought he was going to have a heart attack. At one point I just had to turn around and look at him. Imagine my surprise when I saw that it was Buck Henry.

10 - "Zelig" (1983)

The greatest mock-documentary of all time - including “This Is Spinal Tap,” let's be honest here.

Leonard Zelig is something of a sci-fi conceit. A man so fraught with insecurity that he assumes the personality and physical characteristics of whomever he is next to; a human chameleon. Set in the roaring twenties, “the Changing Man” is presented as a forgotten blip of American history, through fake archival footage that, for 1983, was absolutely groundbreaking.

“Zelig” is a little bit sad and has few laugh-out-loud moments, but it is still rather funny. More unlikely, it manages to be a quite involving love story between Zelig and his caretaker/psychiatrist, played by Mia Farrow. In addition to manipulated newsreels, “Zelig” also splices in footage from a fake Hollywood biopic, offering film theorists multiple ways in which to freak out.

The term “Zelig” is sometimes used to represent a hollow personality, ready to blend in with the crowd. Those who like to ruminate on the Jewish diaspora can sink their teeth into it, too. Personally, I find myself bringing up “Zelig” when extolling the virtues of brevity. This masterpiece is a mere 79 minutes long.

9 - "The Purple Rose of Cairo" (1985)

Of the films on this list sprung from a fantastical “what if?” this is probably the most fully realized. Set during the depression, Mia Farrow is a working class dreamer stuck in a lousy marriage. Her only solace is the movies and she is particularly fond of an average-looking period adventure/romance filled with champagne, art deco apartments and far-flung adventure. After watching the movie countless times, one of the stars (Jeff Daniels) walks down from the screen and into her life.

What follows is a fish out of water tale that is touching and romantic and ultimately heartbreaking. It also gets a tad sci-fi nerdy when the actor that “created” the role (also played by Jeff Daniels) confronts him.

Woody's in full swing here, with great costumes, original music by Dick Hyman and Edward Herrmann perfectly cast as an Edward Everett Horton figure. This was also Dianne Wiest's big break, playing a prostitute who approaches the clueless Daniels.

8 - "Sleeper" (1973)

Woody Allen goes full sci-fi in this antic, joke-heavy bit of inexhaustible silliness. The Woody of the early 1970s wakes up in a dystopian future replete with a fascist leader, robot servants, giant telescreens and, of course, the Orgasmatron.

He enlists Diane Keaton for help in running from the authorities and the two end up trying to topple the government. A climactic scene in an operating theater is among Woody's best Marx Brothers-inspired set pieces ever. I've watched it 400,000 times and I still laugh. The bit where Myron Cohen and Jackie Mason play Jewish robo-tailors isn't too shabby either. Also, Diane Keaton's greatest ad-lib, quite possibly the greatest ad-lib of all time. Instead of saying “shut up” she says “shut up, shut up, just shhhhut up.” Mere print can't do it justice.

7 - "Radio Days" (1987)

Woody Allen has mined the interests of his youth plenty, but was never one to just bask in nostalgia. Until this absolutely captivating look at a childhood in Brooklyn during the 1940s.

This is Woody's “Amarcord” and it is just marvelous. There are universal truths in here that have nothing to do with the setting – and yet the framework provides so much character that it is one of the best films ever made about every day life during the period. The hook of the film – stories triggered by memories tied to radio programs or popular songs – offer a cornucopia of characters and stray anecdotes. There are even leaps into the tall tales concerning the radio stars themselves.

At its center, however, a loving extended family led by Michael Tucker and Julie Kavner, fleshed out by Dianne Wiest and Josh Mostel. Look for a young Larry David and Seth Green and, of course, Woody Allen narrating it all from the melancholy perch of the present.

6 - "Love and Death" (1975)

Pound for pound “Love and Death” has more quality jokes in it than any other movie ever. More than “Monty Python and the Holy Grail” more than “Airplane!” More than Billy Wilder's “One, Two, Three” more than “Raising Arizona.” This movie is brutal, it's non-stop. It's completely absurd and even if you watch it when you are thirteen and don't get all the Dostoyevsky references it is a full-frontal assault of sight gags, wordplay and mania. It's also fairly heavy, loaded with philosophy and some striking location cinematography. But, like, for a second – it's all back seat to the insanity. The bit where he and Harold Gould engage in a duel rocked my young world. And just imagine my surprise when, later in life, I watched Eisenstein's “Alexander Nevsky” and discovered the same soundtrack!

This isn't my favorite Woody Allen movie, but it is probably my favorite pure comedy of all time.

5 - "Manhattan" (1979)

To those who don't know and love Woody, this may be the one that feels the most typical. Shot in black and white and set to Gershwin symphonies, this is aspirational New York lifestyle fetishism to the nth degree. Hyper-intellectuals chatter at art galleries and Bella Abzug rallies and purposely complicate their lives with difficult romantic entanglements. They all have artistic goals, but it's also nice to go out to dinner or fool around with a high school girl (Mariel Hemingway, the only sane one of the bunch.)

Woody Allen and Diane Keaton's rained-out date in Central Park that takes sanctuary in the Planetarium is, probably, the most visually arresting sequence on Woody's entire resumé (thanks in no small part to Gordon Willis' radical lighting scheme.)

I've lived in New York City since the age of 17 and I'm still convinced that this is the way grown-ups live.

4 - "Broadway Danny Rose" (1984)

Woody Allen got into show business at a very early age. This is him giving back to all the old timers he knew coming up.

Framed as a bunch of comics kibitzing at the Carnegie Deli (which does, indeed, offer a Woody Allen sandwich) they start to trade stories about the legendary, lovable loser Danny Rose - the worst, yet most dedicated personal manager. Corbett Monica (who I saw perform once in the mountains as a kid) halts everything when he claims to have “the greatest Danny Rose story.” What follows is an amazing yarn involving the Mob, an lounge crooner and Mia Farrow in her most outside-her-comfort-zone role ever. The comedy is great, as is the intentionally tacky set design and, at times, surreal use of short lenses during trips to the Vitale family compound. This movie even has something resembling a chase scene!

3 - "Stardust Memories" (1980)

Another black and white Gordon Willis collaboration, and this time they pull out all the stops. Riffing on Fellini's “8 1/2” this is by far Woody's most “artistic” picture, his most visually stylized and, while the edit isn't quite as much of a collage as “Annie Hall,” the fact that this is less reliant on jokes makes it feel more surreal.

Woody plays a filmmaker unlucky in love and stuck reminiscing about his life at a weekend retreat dedicated to a retrospective of his films. We see clips of his version of “early, funny ones” and his doomed current film, plus fantasies inspired by observations mixed-in with flashbacks to previous relationships. It's a little jumbled at first, but there is great beauty right beside the humor. Charlotte Rampling is terrific as the “dark woman” in his past, and the concluding gathering of UFO enthusiasts is a tremendous, haunting sequence. Many fans took offense at this film, as if it were a rebuke, but I think it was ahead of its time for discussing the traps of celebrity. Also, one of Allen's most darkly comic lines: “If I had been born in Europe I'd be a lampshade right now.”

2 - "Hannah and Her Sisters" (1986)

Everything that is great about the “Manhattan” is, in my opinion, a little bit better here. This is his most literate film – the one that most reminds me of the work of Philip Roth.

It's fabulous New Yorkers and their troubles, again, but for whatever reason it all gels here. For all the flash and filigree of these characters this is a film that sticks close to basic issues: fear of death, anxiety concerning procreation, desire for love, hesitation making risky moves. Michael Caine and Dianne Wiest both won Academy Awards and Woody won one for best screenplay (one of the fifteen times he's been nominated for that category – a record.)

Of the film's myriad highlights are the title card chapter breaks, the long 360 degree take of the three sisters at a testy lunch and Woody's search for meaning via a short-lived conversion to Catholicism. The framework of Thanksgiving dinners is a remarkably effective way to keep the characters, even with their fancy problems, familiar to us. And the thesis of the film – an epiphany that life might actually be worth living – presenting itself during a revival of “Duck Soup” is just too terrific to deny.

1 - "Annie Hall" (1977)

He had to go with this one in the top spot, huh? Well, Woody Allen's most famous, most respected and most celebrated film is, still, his best film. (Though the last five or so are all basically tied.) This is Woody's only film to win the best picture Oscar, and while some psychopaths think it should have gone to “Star Wars,” the best argument against that are the 93 minutes of “Annie Hall” itself.

Mixing every possible film technique (including animation) and not just breaking but pummeling the fourth wall, this is Woody's best because it comes at the perfect juncture between his “early, funny” work and his more mature, later style. While this is basically a melancholy love story that everyone can identify with, some may forget that there is some really wild, bizarre comedy in here. Characters dip in and out of their own reminiscences (sometimes bringing guests!) and you never quite know when a scene is about to veer into surrealism. Woody talks to a horse, for God's sake.

But at its heart there's Annie Hall and Alvy Singer, two individuals who are meant to be together but also doomed to drive one another crazy. We're lucky enough to join them for the good moments (those lobsters!) and perhaps we grow a bit by watching them break apart. Diane Keaton didn't just change fashion in “Annie Hall,” she changed what a leading lady in a romantic comedy could be. She's spectacular in the film, so when the relationship ends up a dead shark it's all the more heartbreaking.

Also: a Ben Shahn joke.