The best and worst Woody Allen films

So originally I was going to open this article by making a dark oke about how Woody Allen and I are kinda similar because we both like old movies, are sarcastic and date girls born in the early 2000s, but after watching twenty two of his forty eight films, I found myself unable to continue on this project, and I feel the need to explain why. I started this project by watching the films that were commonly regarded as the best, so films like Annie Hall, Midnight in Paris, and other such films which aren’t on either list.

But then those got kind of bland and weren’t breaking into the top five anymore, so I decided to reverse the plan and pad the worst films list by watching the least liked Woody Allen films like Curse of the Jade Scorpion or Scoop. Those got even more bland and dull!

So twenty two films in, I called it quits, as I couldn’t bring myself to watch another movie about a man who hates himself and everyone else, cheat on/be friends with someone who cheats on their wife, with themes about how great New York City is, even though they admit that city still kinda sucks. I also knew that nothing would be better than the films I had already watched, and that any additions to the worst films list would have made me question my love of movies altogether. So, let’s get into the best and the worst Woody Allen films.

Fifth Best – Bullets Over Broadway

Bullets over Broadway is a film that I tried to find to watch for months before finally finding a copy. It’s not available on any streaming service, and most on demand services don’t believe it exists, so when I finally got to watch it, I was cautiously optimistic. If it’s unable to be seen anywhere, would that mean it’s atrocious? Nope. In fact, it’s a great comedy with some great performances.

One of the Woody Allen films which benefits from him not playing the lead, John Cusack is great as the adultering writer, but the real stars of the film are the supporting characters. Chazz Palminteri as the brilliant writer Cheech, Jennifer Tilly as the high voiced talent void Olive, Dianne Wiest as the alcoholic star Helen Sinclair, and even the minor roles like Harvey Fierstein and Rob Reiner are all fantastic.

The film does take a bit to really break into the comedy, but as soon as the second half starts, it’s a laugh a minute film. Overall, a solid yet flawed Allen adventure, that I definitely don’t love, because as we learn in the film, love has to go deep. Still, it’s a solid enough film that if you can manage to find a copy, you should definitely watch it.

Fifth Worst – Magic in the Moonlight

Magic in the Moonlight is a perfectly fine film, but it suffers from being extremely predictable. The moment any story beat happens, you know exactly where it’s going from there. I won’t spoil anything, but if you’ve seen any film like Magic in the Moonlight before- Wait Daulton, what other movies feature a magician trying to defraud another magic user while slowly falling in love with them in 1800s Europe? Um, The Prestige. Anyway, the numerous plot twists hinder what could have been an alright movie, as Emma Stone and Colin Firth do try very hard to make the movie watchable. And that’s what it is, totally watchable.

The cinematography and set design, along with the performances make it good enough to watch one time if you enjoy some Woody Allen films, but it’s predictability weighs it down heavily compared to his earlier work.

Fourth Best – Hannah & Her Sisters

And returning to an Oscar Winning performance from Dianne Wiest, Hannah and Her Sisters has only one thing in common with Bullets over Broadway, and that’s the fact the performances are amazing. Besides that, the strengths and weaknesses are very different. To start, the better half is flipped, as the film definitely goes a little downhill in the second half compared to the heights of the first hour.

Also, the film isn’t very funny at all, but the dialogue is still great. Littered with great monologues, you always know what the characters are thinking and why. Another strength, as mentioned before is the performances. Barabra Hershey, Carrie Fisher, and Max Von Syndow all appear in the film and give great performances. The best performance though belongs to Michael Caine who also won an Oscar for the film as… sigh, an adulterous husband to Mia Farrow. Woody Allen must have really taken it to heart when someone told him to stick to what he knew after the fourth worst film on the list…

Fourth Worst – Zelig

Zelig is actually a well liked movie for… reasons? I mean, it’s definitely different from the average Allen film. It’s a mockumentary about a man who has the ability to transform his physical appearance to that which is similar to the people who surround him, which makes for some very awkward scenes of Woody Allen in… you can tell where I’m going with this, so I’ll move on. My main problem with Zelig is the storytelling.

It wears out its welcome faster than most Allen films. The story feels like it’s over with over half of the movie left to go. It’s remarkably boring, as the mockumentary format makes the film feel very slow. The production and costume design are nice enough, but the plot and acting leave a ton to be desired.

Third Best – The Purple Rose of Cairo

The Purple Rose of Cairo is a magical romcom that gives me hope for humanity, for the first seventy seven minutes. Then the last five minutes happen and it’s the most depressing movie in the world. Jeff Daniels is great in a dual role as both Tom Baxter and Gil Shepard, along with everyone else in the cast. It’s a film of subplots which feel like they could be kind of interesting on their own, all combined to make one great film.

Those subplots include the characters stuck in the screen who have to wait for Tom to come back onto the screen, the executives who are stuck trying to solve the Tom Baxter problem happening all over the country, and the love between Cecilia, Tom, and Gil, which makes for some great comedy. My one gripe with the film is the character of Cecilia’s husband, Monk, played by Danny Aiello.

This one plot thread is so worn and tired that it drags the entire movie down a level or two. One thing that surprised me was that a lot of people don’t like the ending, but I would put it in a similar category to La La Land. A depressing ending which is perfect for the movie that it’s in. The Purple Rose of Cairo is a great film that I really recommend. 

Third Worst – Hollywood Ending

I’ll give it to Allen. He does manage to think of some really interesting plots. Small Time Crooks has a great plot, but is a meh film. The same goes for Hollywood Ending. It’s a pretty interesting idea, someone having to hide their random blindness to keep their job. Mixed with a romance subplot, this could have been a great idea.

What a shame that it had to be attached to such an inconsequential movie! It’s very forgettable, as the way the plot unfolds you keep thinking “Just tell the A.D!” They make a big point about how they can’t trust anyone, but by the end of the film, it feels like everyone on the set knows he’s blind. It’s also a little too drawn out, and the characters are unlikable.

So as a whole, Hollywood Ending is a pretty boring movie that takes a great idea for a movie, but ultimately squanders it with an overlong drawn runtime and characters that are impossible to like.

Second Best – Crimes & Misdemeanours

It was with the second best Woody Allen film, Crimes and Misdemeanors, that I realized a pattern with Allen’s films. A lot of his work from the 80s and 90s, with a few exceptions, are two very loosely related stories. Husbands and Wives aside from a couple scenes are two short films with no relation. Hannah and her Sisters is on a similar wavelength, but with much more connective tissue between plots.

Crimes and Misdemeanors is just two short films that are both really interesting. On one end, we have the standard Woody Allen plot. Affairs, Mia Farrow, and depressed filmmakers. If we just focused on that part of the film, this wouldn’t even crack the top ten. However, it’s the Martin Landau plot, the crime part of the title, that pushes the film over the edge to the Number Two spot. With Landau giving an amazing performance as an ophthalmologist who resorts to murder to save his personal life, this is truly Landau’s movie.

Both plots all come together in the final scene with a great conversation between Allen and Landau, which makes this one of Allen’s best.

Second Worst – A Midsummer Night’s Sex Comedy

Similar with Crimes and Misdeameanors, it was with A Midsummer Night’s Sex Comedy that I noticed a pattern. So much so that I finally coined what I like to call the Woody Allen Drinking Game. While this one does miss out on the “New York” bit, it does hit on every other trope.

Affairs, check. A slightly odd premise, check. Characters who don’t deserve it getting a good ending? Mia Farrow again? Check. That’s my biggest problem with A Midsummer Night’s Sex Comedy, it’s just a Woody Allen mad lib. Character A is married to Character B, but really loves Character C who is married to Character D, who is in love with Character B. The nicest things I can say about the movie is that it’s mercifully short and looks nice. So overall, this embodies the “Seen one, you’ve seen them all” more than most movies.

The Best – Mighty Aphrodite

I debated for a while on whether this or Crimes and Misdemeanors deserved the best spot, but because of a great framing device and Mira Sorvino’s Oscar winning performance, Mighty Aphrodite takes the top spot. The Greek Choir led by F. Murray Abraham is a great way to tell us what the characters are feeling and give one of my favorite musical moments in a film, when they sing the end credits song of “When You’re Smiling”.

With a great cast including Helena Bonham Carter, David Ogden Stiers, Olympia Dukas, and Robocop himself Peter Weller, the cast is one of the best in an Allen film. But the star of the movie is Sorvino, who is wonderful in the role of Linda Ash. Her comedic timing is fantastic, and she manages to switch to the emotional moments really well. I do have one or two problems. Woody Allen as usual plays himself in a role which can be described with about five words “Alvy Singer as a Sportswriter”.

I also think that Sorvino may have watched a bit too many old Mickey Mouse cartoons before filming as the moment someone says she sounds like Mickey Mouse, you can’t unhear it. And I don’t mean that as a bad thing, it’s just a bit distracting once you realize that. But sometimes it does work to make certain lines hilarious, you know exactly which ones I mean if you’ve seen the film. So overall, Mighty Aphrodite is a hilarious film with some great performances. A must see movie.

The Worst – Celebrity

It takes a lot to make me give up on a movie marathon. I’ve made it through all of the seven (at the time) Leprechaun movies, every Friday the 13th film, and every Twilight- well I don’t want to call those movies because that’s being mean to movies, so let’s just say “things”.

Celebrity was the film that made me give up on the Woody Allen marathon. It goes back to the Manhattan model of story as we have a great cast including Kenneth Bragnah, Charlize Theron, Winona Ryder, and Leonardo DiCaprio, all being used in small parts in a black and white New York. The only difference is that Kenneth Bragnah cheats with a twenty seven year old compared to Woody Allen cheating with a seventeen year old. Manhattan truly was ahead of its time. It’s also hugely pretentious in the way only Allen can be.

As one of his longest films, clocking in at 113 minutes (which I know isn’t a lot, but keep in mind Manhattan for all its flaws kept it at a brisk 97 minutes), Celebrity is dreadfully boring. That last bit isn’t helped by the fact that this is such an unfunny film for something which is classifying itself as a comedy. If there was some kind of a child protective service for when movies are incorrectly genred, I’d be dialing right now. So combining bad comedy, a bloated runtime, and so many Woody Allen cliches that Husbands and Wives looks like Eyes Wide Shut, that’s how you get the worst film from an alright director.

So those were my thoughts on ten of the best and worst Woody Allen films. If you’d like to know any others, I can give you a one word description for the ones I didn’t mention “fine”. With the exception of Manhattan, because it’s impossible to watch that film today without being more uncomfortable than one would be watching a deathtrap scene in Saw VI.

I’m sure that the ones I didn’t mention are fine too like Match Point or A Rainy Day in New York. Wait, that last one just came out last year. It had Timothee Chalamet? Oh my gosh, he’s making a movie right now with Christoph Waltz. How is he still making movies even though most of his movies are major financial failures… Unless, Woody Allen made a deal with the devil to write and direct his own movies on the stipulation that most of them would be box office flops. No, that’s impossible.

He would have made a movie about it.

For more Features, be sure to check out our archive and you can read more about Woody Allen on Wikipedia.

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