my favorite Woody Allen movies

it was about time i wrote this

i doubt there are many examples of filmmakers making more than fifty films. that’s the first thing. the sheer number is already an achievement of sorts, and rare. but to have so many good ones, and great ones, and absolute masterpieces among them, is even more rare. so rare that i think really only one man can even come close to claim the prize. it’s Woody Allen.

of course it’s true his scope is very limited. his movies are, in a sense, always the same. but that alone does not make them good or bad. they are what they are, and can be both good and bad. he does have (at most) a handful of terrible movies. but more often than not, he has perfectly enjoyable ones, even when they are nothing special. it’s quality entertainment that does not insult our intelligence, in fact, usually it piques it. at the very least. and then he has absolute masterpieces. at least ten. yes ten. at least.

(oh yeah, by the way, the accusations of molestation against the man are nonsensical, bordering on the absurd; essentially they are the spiteful revenge of a scorned ex wife; and while Woody’s no saint, by all rational measures he is completely innocent, and is guilty only in the court of public opinion; and actually seems to have been a good father, which is rare enough in the arts).

i’m not sure if i watched every single Woody Allen movie, but close enough. these are my favorites, and why i like them. spoilers, of course.

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Annie Hall

funny, charming, entertaining and romantic. it even has Marshall Mcluhan in a comedic cameo. a classic for a reason. and where we should start, because although there were precursors and there is an obvious slow approach in his previous movies to what Annie Hall would be, this is for me, his first truly great movie. it’s where the category ‘woody allen movie’ was really born after being in the womb. and that genre which is his own has influenced, if not created, the whole romantic comedy genre, or at least some of its favorite tropes and beats. and it will be the case for a long time. because Woody has not only created the art. he also perfected it.

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Manhattan

and he didn’t waste time in perfecting it. he’d tried it with Interiors, but it was too dark, too sullen, lacking in magic. with Manhattan we get the serious, black and white response to Annie Hall, but with plenty of magic. a magic enhanced by more tragic considerations, by moral failures which do not resolve in comedy. it also has one of the most powerful openings i’ve ever seen (perhaps only topped by the opening sequence in The Prince of Egypt). and at the end, the definition of bittersweetness, and a plea for faith, for the irresistible yearning not only of, but for faith. it has influenced me greatly.

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Zelig

i haven’t watched many mockumentaries, but this is the only one that i’ve seen that is also a work of art. it’s profound while being absurdly, screwball, belly aching funny. and it’s also somehow profoundly romantic. how the hell do you make a mockumentary be romantic. well Woody did it. it’s also a metafictional philosophical exploration, unlike any other i have ever seen. it’s probably his strangest film. and a masterpiece.

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Hannah and her Sisters

despite the comedy, this is one of the most relentlessly profound movies of his career. profound in character depth, and in themes, and in feeling. three stories, three moral arcs. two end in moral failure, the third, and until then secondary in the film, ends with moral triumph, and the bestowing of blessings. there is order in the universe. against the backdrop of failure given by the other stories, Woody Allen’s and Diane Wiest’s characters’ arcs resolves in such an endearingly satisfying way that doesn’t feel cheap, is earned, and is beautiful. easy contender for my favorite of all.

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Crimes and Misdemeanors

of course, the problem is there are so many contenders for the top. this is another one. Dostoevsky asked, what if crime, but also punishment. Woody asks, what if crime, but no punishment. what if even, no real guilt. at least not most of the time. what if we keep on living with the terrible things we do… and don’t even care. terrifying considerations ensue. but despite the gloom, Woody cannot avoid his deep romanticism. yes the moral man suffers, and the devil remains free. but the latter has already lost. the righteous rabbi, now blind, dances with his newlywed daughter, whom he loves, surrounded by friends and family, while the murderer remains alone, forever alone with his act. yet another beautiful resolution. Allen is a master of the epilogue.

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Deconstructing Harry

i remember when i first watched this movie twenty years ago. i remember being completely floored. first by the metafictional possibilities. the short stories within the movie (and subsequent finding of Woody’s short prose) made me write at least two dozen imitations which were great training for me as a writer. and this specific influence has remained alive for me until now. it’s also one of his only films where the comedy is used to heighten the moral darkness, rather than give us respite from it. but it’s not without its own sort of uplifting message, because Woody is a romantic, as i said, and i can think of only three of his movies ending in complete existential despair. here, it is fiction, imagination, man’s own creativity that comes to his aid. two scenes, both at the end (again, Woody is a master at wrapping things up in the most poignant way), became fundamental for me, from that first watch when i was sixteen years old. Woody plays an author with writer’s block. without his imagination, he has nothing. his friend who is also an author gets the girl, and tells Woody’s character that he puts his heart into his art, whereas his friend puts into his life. that’s why he got the girl, and is happy in his personal life. his friend’s unstated conclusion is that it’s either or. this scene has stuck with me, and i keep coming back to it over and over. but Woody escapes the dilemma by going beyond it in its typical magical realist romantic way. the characters the author created come to pay him an homage. they are his true friends. he has created a world that brought meaning to thousands of people, and that is meaningful. and the reassurance of meaning breaks his writer’s block. another very strong candidate for his best movie.

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Sweet and Lowdown

Woody returns with a no less wacky character study (and partial mockumentary) about a fictional jazz guitarist obsessed with being the best, but knowing there is ‘this gypsy in france’ (Django Reinhardt), who will always be, in his opinion, better than him. the title is exactly right, this movie is about sweet depression. i doubt many would include this one in their favorites, or lists of his best. but to me it must be, and is both. first, it’s funny in a different way from his typical movies. some of it is down to the main character being played by a surprisingly amusing and charming Sean Penn, and not Woody Allen. but it’s really the character, flawed but with heart, which makes the movie be so compelling. he’s a train wreck we love to watch, and feel pity for, and come to love. that, and his relationship with Hattie, a deaf mute that is, in the end, the love his life, his soulmate. something he only accepts too late, providing one of the most heartbreaking endings to any Woody Allen movie. and it really is, perhaps surprisingly, heartbreaking.

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Small Time Crooks

Woody was clearly exploring variations on his comedy and his fictional persona, since this gives yet another type of comic main character. here Woody plays the role of a small time crook, not too smart despite his apparent lack of physical prowess, therefore having nothing to recommend him except the strange charm which Woody always does have effortlessly, whatever character he is playing. the rest of the rag tag cast of small time crooks made rich by accident is also charming and funny. the villain is a high society snob taking advantage of the leading lady’s desire to use her newfound fortune to cultivate herself. this comedy of aspirations and harsh realities is one of the coziest films ever. it’s not flashy, it doesn’t call attention to itself, but it’s one of my favorites. and i return to it often.

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Hollywood Ending

another banger, and one of his best comedies. washed up director gets one last opportunity as a favor from his former wife soon to marry a big producer. Woody starts suffering from psychosomatic blindness just as he’s about to start shooting and directs the movie completely blind, with endless antics of course, all the while getting his former wife to fall back in love with him. yet the blindness remains despite the romantic success. in a twist to Woody’s typical resolution, getting the girl does not save the day. it’s his estrangement from his son that caused him to go blind, as the script he is filming tells a similar story to his own. when he reconnects with his son, his blindness goes away. and for once he sees things clearly. the movie he directed without being able to see anything is of course a complete failure. the critics are unanimous in calling it a piece of trash. except in france. as he candidly puts it: ‘over here i’m a bum, but over there… i’m a genius’. the last scene has the couple leaving for the airport, to go live in the french capital, where hollywood endings are possible. it’s one of the most relentlessly funny movies ever made. every scene is packed with jokes of all kinds, and coming from all angles. it’s just close to the perfect comedy. and it’s also beautiful and heartfelt, in the midst of the belly laughs.

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Anything Else

no one would say this is his best movie, or even a particularly good one. but there is a special charm to it. here Woody plays yet another logical variation of his typical character, in a side role. the prepper type, his neurotic nature manifesting in buying survival supplies and espousing overly paranoid conspiracy theories. yet he is the only one who is consistently proven correct in the movie. the resolution of his side arc is darker than one expects, since the rest of the movie is rather light. and it’s a little unsatisfying too, but necessary for the finale. Biggs makes the first successful stand in for Woody as he became too old for this type of role, while adding a charm of his own. in the end he doesn’t get the girl, and must accept that it’s time for a fresh start. it’s the conclusion that stays with me most. the unspectacular sentence by the cab driver (again on the way to the airport), that the character’s troubles are like ‘anything else’, all the while he is experiencing not one, but two striking cosmic coincidences, wraps it up especially sweetly for me.

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Match Point

i don’t even like to talk about this movie too much. it’s the one case in Woody’s career where there is zero romanticism. zero hope. no doubt the bleakest of his movies. at the end, nihilism seems to triumph completely. the problem is it’s such a stunning, intelligent, perfect movie. at all levels. it’s just overwhelming how perfect it is. i wish i didn’t like it so much. the scene at the start, and how it is reenacted towards the end, and how you think it means one thing but means the opposite, it’s such a strong twist, and yet so simple, so elegant, so logical even. gets me every time. another contender for one of his best movies. certainly the most serious. and the most dark. i wish it wasn’t so good, because the questions it raises can keep anyone up at night.

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Midnight in Paris

Match Point could have ended up being the last of Woody’s great movies, but the romantic in him had to have the last word. in my good days i think this is his best movie. magical realism that is more magical than realist, full of romance and yearning and nostalgia and charm and more and more. it’s almost a love letter to his own vision, again unsurprisingly set in Paris rather than New York. perhaps only in Paris he is able to believe it, like in Hollywood Ending. Paris is where he dares to dream most, and here he dreamed the perfect romantic comedy. moving, and beautiful, and sweet, and always funny. also Owen Wilson as stand in for Woody is an inspired choice. the best non-Allen Woody, no doubt.

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after this Woody has made a few more films. none of them are among my favorites. most of them are not good. some are ok. three are ok, or even good (Blue Jasmine, Café Society and A Rainy Day in New York), but only that, and i am in no rush to watch them again after the first time.

there are plenty of honorable mentions, that is, movies that are good or even great but are just not among my absolute favorites. Love and Death, Stardust Memories, Purple Rose of Cairo, Mighty Aphrodite and Scoop come to mind. the first three it could and has been argued, are also among his very best. Scoop also has a special place for me, i find it quite charming and fun, but objectively speaking it’s nothing special, except perhaps for the fact that Scarlet Johansson can be really funny, it turns out.

one thing left unmentioned is the music in his films, which is always on point, and beautiful, and also peculiar, and part of his special style.

i’ve lost count by now, because Woody has just too many good movies. it’s actually insane. and his novel, written at eighty nine years old, is actually better than his more so so movies. and he’s writing another one. the romantic lives on.