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Peak Decades: Woody Allen

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As every decade has its own flavor, its own vibe, I thought it would be interesting to see when some prominent directors/actors were doing their best work. Sometimes its easy- while Francis Ford Coppola has been making movies since the late 60’s, it is clear that the 1970’s were his peak decade (and possibly the best run that any director will ever have-Godfather 1 and 2The ConversationApocalypse Now). There can’t even be an argument there, right?

But what about other artists who have been working for a while?  Was there a particular decade in which they were doing their best work?

The criteria is as follows:

  1. The artist had to have been active in their field for at least three full decades.
  2. Artistic merit only, and by that I mean my opinion of artistic merit.  Not gonna worry about the decade they were most financially successful.  This will change which decade Nicolas Cage did his best work, for instance.
  3. While I will list everything the person has done in each decade, I will compare what I think are the best three.  There will probably be a few I haven’t seen, and will note those as well.
  4. I will only look at complete decades- no “Decades in Progress.”


So, Woody Allen.  Obviously, there are a number of approaches to take here when considering in which decade he did his best work; do you look at him solely as a writer?  Actor?  What about his beginnings as a stand-up comedian in New York?

I decided that the best lens in which to look at Woody is through his directorial efforts, specifically his major films (of which he has been averaging one a year for 40 years!).  Even though he has directed a number of plays and TV movies in that time, they will for now be ignored.  Besides, I don’t think “Men of Crisis: The Harvey Wallinger Story” from 1971 will make much of an impact in his 1970s output, especially when put up against an Annie Hall or Manhattan.

Additionally, he only directed two movies in the 1960s:  What’s Up Tiger Lily? In 1966 and Take the Money and Run in 1969.  I want to start looking at his stuff in the 1970s, when he had a full decade to lay down the Woody flava.  That said, I prefer Take the Money and Run to Tiger Lily, if only for the botched hold-up scene.

The 1970s:

 Directed:  Bananas, Everything You Wanted to Know About Sex *But Were Afraid to Ask, Sleeper, Love and Death, Annie Hall, Interiors, Manhattan

Best Three:  Love and Death, Annie Hall, Manhattan

Worst:  None are terrible, although I’m not a huge fan of Sleeper.


Of Woody’s early “silly” comedies, I like Love and Death the best. But I’m one of those people who weren’t all that sad to see him leave the wackiness behind, so I guess Stardust Memories was superfluous for me. Woody’s take on Tolstoy and Dostoevsky doesn’t seem like it would translate to comedy, but the guy has always infused darkness and despair into his laughs. In fact, the two concepts of comedy and death are so intertwined in his work that it is impossible to separate them. A lot of people say that Annie Hall was the perfect bridge between his early comedies and his later, drama-infused smilers. But I dunno- I think that Love and Death works as that transition movie just as well.  Think of it this way:  if Annie Hall is Woody’s Revolver, then Love and Death is his Rubber Soul.


The big one, right?  To this day, this is the movie that Woody is most associated with (rather than the story with which he is most associated which is when he married his stepdaughter.  But we’ll look at that when we talk about Husbands & Wives). But Annie Hall deserves every accolade it gets, even beating Star Wars for Best Picture. Here’s why:  with this movie, Allen rewrote the rules of romantic comedies.  Every single romcom from this point forward share a little of Annie Hall’s DNA, but most forget the innovation Woody employed. Oft mentioned is the breaking of the 4th Wall throughout, most famously when he produces Marshall McLuhan in line for The Sorrow and the Pity. But how about the disjointed narrative that jumps back and forth in time? The use of subtitles to highlight the differences between what we say vs. what we think? The fact that this most romantic of romantic comedies ends with the couple split apart?  An animated sequence?   Annie Hall is not my favorite Woody Allen movie, but it belongs in the discussion of most important films in the Allen canon.


Manhattan is my favorite Woody Allen movie. It is a much more straightforward movie than Annie Hall, sacrificing much of the experimentation for what is now the absolute prototype for the romantic comedy done right. From the Gordon Willis B & W cinematography (has NY ever looked better on film?) to the atypical opening credits (eschewing his typical white Windsor font against black for the movie’s title represented by a blinking billboard). The cinematography makes the movie feel more “arty” than it actually is; in fact, this is one of the basest versions of the “Woody” persona that he’s ever shown us. Isaac Davis is self-absorbed, delusional, and fairly immoral in his relationship with a high school student, but Woody sells it with the ending, which has Isaac doing all the right rom-com grand gestures and still not getting the girl.  Perfect.

Runner Up:  Bananas

The 1980s:

Directed:  Stardust Memories, A Midsummer Night’s Sex Comedy, Zelig , Broadway Danny Rose,  The Purple Rose of Cairo, Hannah & Her Sisters, Radio Days, September, Another Woman, New York Stories (Oedipus Wrecks), Crimes & Misdemeanors

Best Three:  Zelig, Hannah & Her Sisters, Crimes & Misdemeanors

Haven’t Seen:  September, Another Woman

Worst:  New York Stories (Oedipus Wrecks)


Zelig deserves a lot more credit for creating the mockumentary craze that continues unabated to this day, not to mention the debt Forrest Gump owes to it. Yeah, This is Spinal Tap came along the next year and really set the template for the Christopher Guest/The Office/Modern Family talking head style that is so prevalent today, but Zelig did it first and with much more verisimilitude. In fact, you could show Zelig to someone and sell it to them as an honest-to-God documentary, at least until Woody morphs into an obsese man or a black jazz musician.  Working again with Gordon Willis, Woody was as hungry and innovative a filmmaker that was working in the early 1980s, using vintage cameras and physically damaging the film to create the aged look he needed for the movie. Beyond it being an astounding technical exercise, it has a lot to say about a person’s identity and how we change to fit our audience.  All that, and it doesn’t overstay its welcome at 79 minutes. I don’t hear a lot about Zelig these days, and that’s a shame.


Woody certainly trucks in existential questioning, but never more entertainingly or profoundly than in Hannah and Her Sisters. This isn’t even the “main” story of the movie, but the character Woody plays (Mickey) uses his hypochondria as a springboard to question first religion and then the very meaning of life. These aren’t easy topics to incorporate into a comedy (unless, apparently, you are Woody Allen), but he does it in such a funny and relatable way here that his emotional journey remains the most memorable thing about the movie for me. Who hasn’t found a weird bump or mole or pain in or on their bodies that caused their minds to run rampant until cancer is the only reasonable cause? The moment when Mickey receives the good news that he is healthy only to stop mid-jubilance to realize that his demise has only been put off, not prevented, is one of the most truthful things I have ever seen in a movie.  The fact that this subplot is only one part of a larger tapestry of connected plots, of which all work superbly, by the way, make Hannah a contender for Woody’s best.


A movie split in two but united by a common theme: is God watching us or is everything that happens just a matter of chance? That is some heavy-duty material to wrestle with, even by late 1980s Woody Allen standards. But pull it off he does, courtesy of a never-better Martin Landau coupled with a dream-team pairing of Allen with Alan Alda. The Landau stuff first: as an optometrist who has an affair that turns into threat to his way of life, Landau shows both the moral wrestling match of having to deal with his situation or use his mob-tied brother to “take care” of the woman. His decision, and how he lives with it, is dark of the jet-black crayon variety. Allen juxtaposes this plot with a much lighter one but no less demonstrative of his theme.  Allen, as Cliff, is a documentary filmmaker who is in love with the producer of his latest film, a puff piece about a successful television mogul. He hopes that he can woo her with his integrity and intelligence; she instead falls in love with the charming and powerful TV mogul, played by Alda. “This is my worst fears realized!” Cliff cries when he discovers the truth. He hoped that some cosmic justice would prevail and the girl would end up with the “right” guy. But is there anyone truly looking out for the little guy?  Is God watching?

Runners Up:  Midsummer Night’s Sex Comedy, Broadway Danny Rose, Radio Days

The 1990s:

Directed:  Alice, Shadows and Fog, Husbands and Wives, Manhattan Murder Mystery, Bullets Over Broadway, Mighty Aphrodite, Everyone Says I Love You, Deconstructing Harry, Celebrity, Sweet and Lowdown

Best Three:  Husbands and Wives, Bullets Over Broadway, Deconstructing Harry

Haven’t Seen:  Shadows and Fog

Worst:  Celebrity


Husbands and Wives was the last of Woody’s movies made before The Scandal. Of course, it was released after it came to light that he was carrying on a relationship with Mia Farrow’s adopted daughter, but the public (and Farrow) had no idea while this movie was being made. I’m sure Farrow thought she’d be making Woody Allen movies for the rest of her life; ah, fate. To be fair, Woody has been outing himself as a cradle-robbing letch for some time now, as early as Manhattan. And he’d keep on doing it after Husbands and Wives as well, but never has that side of him seemed more pronounced than in this movie. The affair between Gabe (Allen) and one of his students played by Juliette Lewis became the main talking point in the film, but to only focus on that does not do this movie justice. First, Mia Farrow has to be given credit for playing one of the more manipulative and complicated women in the Allen canon; she plays her character of Judy as meek and passive at the outset, only to be revealed at the end as controlling and dominant. One has to wonder if this is how Allen saw her in those last few years…. But top drawer performances abound in Husbands and Wives, with special mention going to Judy Davis and Sydney Pollack as a separated couple who act as the catalyst for Judy and Gabe’s split. The direction of this movie is interesting as well; scenes and dialogue are cut off before they finish, characters drift in and out of frame… I suppose you could accuse Allen of utilizing the dreaded “Shaky Cam” here. But it is used here to represent the shaky ground these characters inhabit, and by the end it is Gabe himself who ends up alone. Again, I doubt Allen would ever write something that he would identify as “autobiographical,” but of all his movies, Husbands and Wives has to come as close as we’ll maybe ever see.


Bullets Over Broadway represents the first of my favorite Allen movies that doesn’t actually contain a performance by Woody himself. After this movie, it seems to me that he had a more difficult time knowing when to step aside for a role; maybe because it is so difficult for actors to step into the “Woody persona.”  That said, it was absolutely the right choice here, as Woody the actor would not have worked as a struggling young playwright. John Cusack works just fine in the part; in fact, I’m not sure anyone did it better than him except for Michael Caine in Hannah and her Sisters and later, Owen Wilson in Midnight in Paris. The story, which focuses on how far an artist will compromise his art (and who is really the “artist” at work), is as funny as anything Woody has ever done, with two of the best characters he has ever written. The first is Helen Sinclair, played by Dianne Wiest in the second Woody Allen role for which she won an Oscar. She nails the dramatic pomposity of this aging actress, constantly insisting on “silence” with John Cusack’s David. The other character is Jennifer Tilly’s mob moll, Olive. It takes a very smart actress to play someone so dumb so well, and Tilly nails it (and earned herself an Oscar nomination as well).


I think Deconstructing Harry would make a good double feature with Husbands and Wives in the sense that it seems as if Woody Allen is throwing down a mea culpa about himself in both. I could be wrong there, and as I said before, Woody doesn’t seem like the type of guy who is going to every admit to anything being autobiographical. Still, the idea of a writer who uses the people in his life as inspiration for his nasty stories has to be based on something Allen himself lives, or has lived, through. The “Woody” character that has been present in so many of his movies has never seemed this sad, nasty and poisonous. Many of the themes he has revisited time and time again are present here: what constitutes art and you have to sacrifice in your daily life and relationships to achieve that art (he revisited some of these ideas again in Sean Penn’s character in Sweet and Lowdown). I think Deconstructing Harry is one of his most underrated movies; it isn’t easy to like and it’s a bit disturbing to see him move beyond simple neuroses into flat-out self-loathing. Still, the 90s saw Allen at perhaps his most honest in terms of the stories he was telling.

Runners Up:  Everybody Says I Love You, Sweet and Lowdown

The 2000s:

Directed:  Small Time Crooks, The Curse of the Jade Scorpion, Hollywood Ending, Anything Else, Melinda & Melinda, Match Point, Scoop, Cassandra’s Dream, Vicky Cristina Barcelona, Whatever Works

Best: Vicky Cristina Barcelona

Worst: I guess Whatever Works


The 2000s haven’t been my favorite decade for Woody Allen movies. Up until The Curse of the Jade Scorpion, I made it a point to see each of his films in the theater. Jade Scorpion cured me of that, and I never regretted waiting for, say, Hollywood Ending or Anything Else, to see at home. A lot of people feel that Match Point was the highlight of this decade, and while I liked it well enough, it seemed like it was drafting off Crimes and Misdemeanors a bit too much for me to take it all that seriously. If I had to pick one movie that I thought was great… well, there would be none, I’m sorry to say. But Vicky Cristina Barcelona came the closest, I suppose. It seemed smaller in terms of themes and benefited from him not swinging for the fences. Javier Bardem and especially Penelope Cruz (who won the Oscar for her role) were a good fit for Woody’s dialogue, and Rebecca Hall did a nice job covering for Scarlett Johannson’s deficits. I think the best thing about it was the locale, as Barcelona looked unbelievably beautiful. It has been said that nobody shoots New York better than Woody Allen, and he brings that same loving eye to this movie as well.

So there it is.  Are the 1970s, in which Woody made the transition from straight comedy into something deeper, creating two all-time classics with Annie Hall and Manhattan?  Or is it the 1980s, where we saw Woody experiment with the form, innovating and recreating with each new film?  The 1990s, in which Woody got much more personal with his movies, and what they sometimes lacked in consistency, they more than made up for with a new honesty that audiences had not seen before?

Three decades of movies, each of which makes a strong case for being Woody Allen’s peak decade. For me, it is the 1980s. Yes, my favorite movie of his is from the 1970s, but in a decade that he gives us not only Zelig, Hannah and her Sisters and Crimes & Misdemeanors, but also Broadway Danny Rose, Radio Days, The Purple Rose of Cairo, and A Midsummer Night’s Sex Comedy… well, that streak has to be respected.  Even Stardust Memories, a movie I still can’t find a way into, was audacious in a way that makes later films like Small Time Crooks or Manhattan Murder Mystery look very small indeed.

If there were a second place, I’d go with the 1990s over the 1970s. It was spotty for sure, but Allen was doing some stuff there that felt so much more personal than at any other point in his career.

Woody Allen’s Peak Decade:  The 1980s


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