Movies by Woody Allen: Ranking His Filmography from Worst to Best (Including Blue Jasmine)

10. Radio Days (1987)

I sort of feel like I’m punishing it for being a breezy, I.V. drip of nostalgia, a bag of kaleidoscopic cotton candy. It’s like sitting around listening to stories at a nursing home full of the greatest storytellers of the radio generation. It reminds me of Amarcord and the Royal Tenenbaums; a rich, colorful and inspired ensemble that weaves together perfectly. Very uncommon. This should be higher. But where?

9. Midnight in Paris (2011)

Instant classic or not, it’s only been two years. That’s why I can’t rank this recent release any higher. Perhaps I am plagued by what Paul — yes, the pedantic pseudo-intellectual — called golden-age thinking. To me, the golden age of Woody Allen is 1977-1992. When it comes to fantasy Woody Allen movies, however, only The Purple Rose of Cairo is superior. Is the movie a tad bit sugary? Yes. Does it tread on familiar terrain? Yes. Who cares? This whimsical joyride about longing to live in a previous, presumably better, era never gets old. It’s Groundhog Day-ish in that regard. Thank you, Wes Anderson, and thank you, cheesy rom-coms, for letting Woody borrow Owen Wilson. I’ve probably watched it a dozen times already. It’s one of my mother’s two favorite Woody flicks (along with The Purple Rose of Cairo). Why? People love this movie because it’s a lot of god damn fun, but also because it’s real. It’s hard to face that now might be as good as it gets. With movies like Midnight in Paris, it’s a little less difficult.

8. Match Point (2005)

Woody’s 21st century comeback film. That’s not even the most impressive part. Match Point is a departure movie. It almost feels like someone else directed it — Robert Altman, Roman Polanski or Sidney Lumet, maybe. I mean that in the most flattering way. The biggest Woody Allen criticism is that all his movies have his personality, his cinematic thumbprint if you will, carelessly smudged all over the place. That Woody Allen is always Woody Allen. In this chilling English thriller, his imprint is completely missing. If you took the Pepsi Challenge here — with a great understanding of film but no clue who made this movie — there is no way you’d guess who directed it correctly. Think about it this way: Woody Allen proved here that could direct a Polanski-like thriller, but could Polanski direct Bananas? Or Bullets Over Broadway? Or Zelig? Polanski kinda tried to do Woody with Carnage, a Woody-lite movie that he didn’t write (disclaimer: I love Polanski as a filmmaker. Chinatown is among my favorites). Allen’s versatility is dismissed as if all 43 of his movies are clones reproduced using the nose from Sleeper. Back in reality, he has one of the most exciting and versatile filmographies of all time. He’s like the Coen Bros.; except there’s only one of him and he’s made three times as many films. Anyway, if you or someone you know can’t get into Woody, try this as a gateway drug. It’s smart, sexy, slick and modern.

7. Deconstructing Harry (1997)

I probably need to write an entire column on why I think this movie is one of his finest films. Upon doing some research, I was pleased to discover that fellow Woody-lover Will Leitch, he of Deadspin fame, wonders if Allen considers this his masterpiece. It’s pre-Charlie Kaufman Charlie Kaufman. It’s 8 1/2 on crack. It’s Wild Strawberries meets John Waters. An author using personal anecdotes as inspiration, only to wind up in personal trouble when he enjoys success as a result. That is the perfect, the perfect, plot for a Woody Allen movie starring Woody Allen. I’ve deconstructed Deconstructing Harry many times. The more I watch it, the more I feel like it is misunderstood and waaaaaaay undervalued. Give it another watch.

6. Husbands and Wives (1992)

President, Judy Davis fan club. Guilty as charged. Her role in this tale of torn lovers was the second greatest performance in an Allen picture. I remember it feeling more real than anything else in the entire filmography. Except maybe September. Which was also real boring. It’s also vastly more enjoyable than his hard-to-swallow Ingmar Bergman rip-offs, Another Woman and Interiors. OK, OK, maybe September bit Bergman’s style, too. Anyway, despite how emotionally charged it is, I find this 1992 classic extremely rewatchable.

5. Hannah and Her Sisters (1986)

My mom is one of three sisters. My brother’s wife is one of three sisters. My girlfriend is one of three sisters. Perhaps that’s why this movie hits so close to home. Nevertheless, it’s a brilliant Woody release even if you don’t have a personal connection to its material. All aspiring thespians should be required to watch this before they appear on stage or screen. It’s an acting clinic. Dianne Wiest (who’s a bit of a lucky rabbit’s foot for Allen) and Michael Caine in Academy Award-winning roles.  Barbara Hershey (yes, the wonderfully creepy mom in Black Swan). Max von Sydow (yes, the creepy knight from The Seventh Seal). Former muse Mia Farrow. Carrie Fisher. John Turturro. Julia Louis-Dreyfus. It’s an amazing cast and amazing movie. Not quite Woody’s finest effort, but damn, damn close. These top five are neck and neck, undoubtedly some of the finest American films ever made.

4, 3. Annie Hall (1977), Manhattan (1979)

I’m probably going to catch some serious flak for ranking these two classics third and fourth instead of first and second. Annie Hall and Manhattan are certainly his most celebrated films. This late-70s dynamic duo is the starter kit for non-fans, and the one-two go-to punch for critics when discussing his filmography. Whatever. Doesn’t matter. Popular consensus isn’t always right. Actually, in modern-day America it’s almost never right (a popular Allen topic).  In my opinion, he’s created two better motion pictures. Movie-going is about the most subjective experience on the planet. And this is just my opinion… but I’m sure many of my fellow Woody die-hards (or blowhards, depending on who you ask) feel like these films are a tad overrated. I’m not saying Annie Hall didn’t deserve to win Best Picture. I’m saying other Woody Allen pictures should’ve won Best Picture, too. I’m not saying Manhattan isn’t one of the best films ever made. I’m saying it isn’t the best film Woody ever made . Those of us who have dug deeper, re-watching all of his films multiple times, know that there is much more to the man then these two masterpieces. Hell, perhaps I don’t have them ranked first and second out of spite. I just feel like if Annie Hall and Manhattan are your two favorite Woody Allen movies, then you need to watch more Woody Allen movies. But I still love me some Annie Hall. And Manhattan.

2. The Purple Rose of Cairo (1985)

Much like Network, this prescient movie is even more relevant now than it was back in 1985. Allen has always been obsessed with, well, our obsession with fame and celebrity. How Americans in particular live vicariously through their stars, soaps and now Reality TV. That’s the foundation this country was built on — that we can all truly have it all. Problem is, we can’t have it all, especially by escaping into entertainment (Hypocrite alert: As I notice I am writing a 3,500-word article about 43 movies I’ve watched multiple times). Whether we’re watching American Idol or some old black-and-white film we imagine ourselves literally getting pulled into, the entertainment eventually stops. Then we must return to real life, even if our life sucks. That isn’t always fun, or fair, and this fantastical story underscores that. That’s the ugly side of this film. The beautiful side is that movies can offer us a two-hour refuge, like they did for Mia Farrow’s Cecilia. For me, when I’m sad, bored, anxious, angry, confused, stagnant, stuck, uncomfortable, too comfortable, heartbroken or in love, the movies give me just the right medicine. Sometimes it’s pure escapist fare. It can help us get through life’s struggles. Sometimes it challenges my mind, gets the creative juices flowing, kickstarts the brainstorming process (Although Woody is right — the shower is the best place for this). Other times it’s a wake-up call, a cold, hard cinematic slap. Occasionally, I walk away wiser, or more appreciative. After viewing The Purple Rose of Cairo, I certainly did. I even chuckled three dozen times in the process. I call that movie magic. It deserves this slot.

1. Crimes and Misdemeanors (1989)

Maybe I have seen too many movies, especially Woody Allen movies? Even if I do need to get a life, I’m telling you this is the best of the bunch. Martin Landau put forth the finest acting performance out of the entire 4,897 minutes* of Woody Allen celluloid (* – I have no clue how long all his movies are when added together. It’s 4 AM and I’m already 3,500-plus words deep. Gimme a break here.). Not only that, but also the best performance of Landau’s entire career. Screw Tucker: The Man and His Dream. Screw North by Northwest. Screw Ed Wood. Screw Entourage. This. Is. It. It’s also the finest acting performance of Woody Allen’s career. He was flawless in this New York morality tale. Alan Alda and Anjelica Huston both shine in supporting roles again (told you I’d get back to that). If you enjoy dramatic rise-and-fall crime sagas like Breaking Bad and The Godfather, rent this one immediately. Eff that. Jump on Amazon and buy it for four bucks used. Even if you have seen it, you should own it. This is Woody starting us off with a great man and leaving us with a monster. Allen has specialized in being both hilarious and heartbreaking, his entire career, but he’s never done both things at once so masterfully. This one makes me glad I see too many movies. It also makes me glad that I don’t always want a “happy ending.” Woody Allen is all about celebrating life’s horrible, hysterical and heartwarming moments for the little while they last. No Allen movie embodies all of that better than Crimes and Misdemeanors.