The Top 10 Films of Woody Allen

He’s been directing films since 1969 (debuting with the hysterically funny “Take the Money & Run“) — about 40 in all. Some are modern-day classics, some very good, others not so great, and then there are those handful of films that were, well, just hard to stomach. I have remained a loyal, ardent fan of his short stories, plays and films for years. When there is a new Woody Allen film, I will most surely go out and pay my $10 to see it. Here is (for better or worse) my Top 10 Woody Allen Films of All-Time; a very difficult list to put together, I assure you. I desperately tried to squeak “Deconstructing Harry” or “Take the Money…” in there, but alas, ten spots goes pretty quickly. All ten films are outstanding in their own ways. Give it a read — and please make sure to let me know what you think…where you agree, where I was led astray and anything else you might like to add. Your comments are always welcome. Enjoy!

10. SWEET AND LOWDOWN (1999)

In my opinion, the last film of Woody’s that I can actually classify as “great.” A great mix of comedy and drama in this one with Sean Penn in the lead role as Emmet Ray, the world’s second greatest guitar player behind Django Reinhardt. Unlike most actors who take on the male lead when Woody takes a backseat, Penn does his own thing; not becoming the typical Woody-archetype (the perfect example being Kenneth Branagh basically mimicking Woody throughout the dreadful “Celebrity“) – and he is nothing less than sensational, giving one of his best performances in a career filled with so much strong work. In Emmet Ray, Penn creates a despicable, immature, conceited, narcissistic, rude human being who cares about nothing but his music – and Django Reinhardt. When he meets Hattie, a mute, simple gal, his life is turned upside down. As Hattie, Samantha Morton breaks your heart. She is simply adorable here and without saying one word through the entire film, earned a well-deserved Oscar nomination. She matches Penn in each scene they share merely with her body language and facial reactions. Two great actors here and it is so enjoyable (though at times painful because of how Ray treats her) to watch.

The music used throughout the film is sensational – one of Woody’s best compilations. I never get tired of the soundtrack. Another period piece, the look and feel (from art direction to costumes) is wholly authentic. A smart, insightful script by Allen. In the end, this comedic “biography” plays out like a tragedy. One of the definitions of the tragic hero is that he/she brings about his/her own downfall. Here, we watch as Emmet Ray does just that. And as miserable as he is, we still have compassion for him throughout – a testament to the work of Sean Penn here under Woody’s subtle direction. It is tough to make a top ten list of Woody’s films without trying to make a spot for this winning film.

9. INTERIORS (1978)

Following the phenomenal success that was “Annie Hall” came this film, Woody’s first entirely dramatic film, sans any humor really at all. In fact, during a dinner scene when the characters are all laughing at a joke, we never even get to hear the actual joke. Another note: this is the first film Allen directed in which he did not act in at all.

Of all his films, this is the one that most resembles that of Ingmar Bergman – in theme, story and how it is shot (by his longtime collaborator, Gordon Willis). The entire film takes on a very somber, pragmatic aura. Arthur (E.G. Marshall) decides to leave his overbearing wife (Geraldine Page). The three daughters must now come to terms with this as they also come to terms with their own lives and their own relationships with one another. The family is an artistic one: one daughter is an actress, the other a successful writer and the third, is trying desperately to find her artistic niche. Diane Keaton, Mary Beth Hurt and Kristin Griffith play the trio of sisters. Geraldine Page as Eve sparkles in this very demanding role of the matriarch of this dysfunctional family. She is the nucleus of this film. Maureen Stapleton is great comic relief (if you can call it that) and she brings great life and color to this otherwise bland, upper-class, eastern Long Island existence.

Though nominated for 5 Oscars, the film is not for everybody. In fact, I would only recommend this one to devout fans of Woody Allen. I surely wouldn’t cite this film for someone to watch if he/she was just starting to view his films. I look at this particular work and appreciate, admire and enjoy it. After churning out those “early, funny” movies, this was quite a daring move. And the performances here are bold and strong. I admit, I need to be in a certain mood to watch this one, but it does truly stand out as one of his finest, most mature efforts.

8. LOVE AND DEATH (1975)

Classic early Woody Allen comedy and one-liners here. Filmed mostly in Hungary, the film revolves around the ultimate coward, Boris Grushenko (Woody Allen) being forced to enlist to save his country from an invasion by Napoleon himself. Most improbably, Boris becomes a war hero and he may now finally make for an ideal partner for Sonja, the woman of his dreams (Diane Keaton), who always preferred his brother Ivan to him. The film is filled with timeless banter between Keaton and Allen here – such a pleasure to watch. When Sonja finally relents to Boris’s proposals, she convinces him to help her assassinate the French dictator.

In addition to some very clear references to Ingmar Bergman’s “Persona” (the camera angles of various close-ups during the infamous “Wheat” scene) and Dostoyevsky’s works, Woody is his hilarious, incompetent, psycho-babble self. When the Countess tells him he is the greatest lover she has ever had, Boris deadpans, “Well, I practice a lot when I am alone.” Nothing cracks you up like a primo masturbation joke. The blithe music of Prokofiev works well here and the script harkens back to Allen’s earlier prose tackling such subjects as love, loyalty, fear of death, honor, and morality (“If it turns out that there IS a God, I don’t think that he’s evil. I think that the worst you can say about him is that basically he’s an underachiever”). Like his prose, Allen manages to face such profound themes by way of slapstick and comedy. A wonderful comedy and a pleasure to watch anytime.

7. THE PURPLE ROSE OF CAIRO (1985)

Woody has said on a number of occasions that this was his personal favorite of all his movies. If nothing else, it may certainly be the most original and compelling, simply for the premise alone: Set in New Jersey during the Great Depression, Cecilia (Mia Farrow) needs an escape. An escape from her tedious job as a waitress and from her abusive husband, Monk (a nasty Danny Aiello). She goes to the movies. Here she sees the handsome and enchanting Tom Baxter (Jeff Daniels) in the film “The Purple Rose of Cairo.” She goes again and again until one day…Tom just walks off the screen – and into Cecilia’s life. There is a problem though: Tom is not…you know, real! While Cecilia and Tom begin their own fascinating relationship, Hollywood execs are furious as they discover that Tom Baxters across the country are leaving their own movie screens. This is amazing stuff — what more can you ask for?!

Woody’s period pieces always feel quite authentic and this one is no exception. He has always written wonderful, 3-dimensional dialogue for women – again, this film does not disappoint. Jeff Daniels plays the 1930’s movie star with pizzazz, dignity and good humor. Things really get interesting when he begins to realize that this very real world is different than the imaginary one he just escaped from. There is also some very funny banter between the characters on screen waiting to see if Tom will return to them so they can get on with their own (movie within a) movie. An ingenious screenplay with a tremendous heart, this one goes right at #7, though I can fully understand why Woody himself places it at the apex of all his work.

6. BROADWAY DANNY ROSE (1984)

There are the films known as Woody’s old, ridiculous comedies (“Sleeper,” “Bananas,” “Everything You Always wanted to Know About Sex…” etc.). Then he began getting a bit more dramatic. And then he went back to full-out comedy with this delightful and uproarious black-and-white film. Now for many, you either love Woody’s humor or you don’t. Not much room in between. He certainly is an “acquired taste” and has his own style/brand of humor. But if you like his comedy and haven’t seen this one yet – do yourself a favor and go rent it…now!

Woody plays Danny Rose, a very unsuccessful talent agent with a heart of gold. He goes above and beyond for his bizarre list of clientele. His one big client is Lou Canova (Nick Apollo Forte), who stays with Danny more out of loyalty than anything else. Canova hasn’t been big for quite some time, but now has a chance of making a tremendous comeback that would pay off for both. He asks Danny Rose to do him a huge favor…make sure his mistress Tina (Mia Farrow) is there to see him perform at a very important concert. Canova is married, so Danny and Tina must play off like they lovers. What happens from there is great comedy from Woody – original and warm…downright hilarious stuff. This makes the final scenes between Tina and Danny so effective…it really does hit you in the gut.

Woody’s comedic acting chops shine here. And Farrow, as the Italian broad is equal to the task. Woody has made a career out of playing the “loser” type who is down on his luck. Danny Rose is the epitome of this model, but we sympathize with this character 100%. The Thanksgiving Day dinner scene is a sad, tender one. His advice to his pathetic clients is classic Woody and him trying to get them work is even more hilarious. When trying to get a booking for an unimpressive client, Danny says, “My hand to God, she’s gonna be at Carnegie Hall. But you – I’ll let you have her now at the old price, OK? Which is anything you wanna give me. Anything at all.” Great stuff.

The film though belongs to the adventure that Tina and Danny go through. The helium balloon scene by itself is classic. In a new age of comedy films (either Judd Apatow, teen comedy flicks, Tyler Perry, et al), none of them measure up to this comedic classic…not to me at least. This stands as one of Woody’s best.

5. HUSBANDS AND WIVES (1992)

In the wake of Woody’s well-publicized scandal of a break-up with longtime companion Mia Farrow came this harsh, raw and wonderful film in 1992. Woody has admitted that he wanted to break the traditional rules of filmmaking here and he does so, using hand-held cameras, breaking up scenes in the middle of dialogue and not caring one way or another if the camera was on the front, side or back of the head of a particular character on screen. It does have the style and feel of a pseudo-documentary, complete with narration given by the film’s costume designer, Jeffrey Kurland.

The film opens with Sally and Jack (Judy Davis and Sydney Pollack) announcing to their best friends Gabe and Judy (Woody and Mia Farrow) that they are separating. Jack has taken a much younger lover who may be too much too handle for Jack – and yes, perhaps a little too dumb as well. Judy is way too highbrow for this sort of thing, but she does try to get back out in the dating world once again, even if her prime years are long behind her. Gabe and Judy have the seemingly perfect marriage at the film’s onset. But Allen here delves into and analyzes the long-term effects of being with the same person for years on end. And if you are aware of his works, you know that it won’t end well. Gabe is a college professor and he is soon tempted by a young, fawning, overly-sexed student (Juliette Lewis) that threatens to break up Gabe’s stable world.

I loved this film. I loved how Allen shot it, though many have told me that the constant camera movement made them somewhat nauseous. All of the actors are at the top of their games here. I am not a Mia Farrow fan at all and never thought she made much of an ingénue for Allen (unlike the ever-stronger Diane Keaton) throughout the course of their longtime collaboration, but here she does an admirable job. The wonderful filmmaker Sydney Pollack is very strong here and is quite natural in front of the camera, at odds with his wife and opening up to his close friend, Gabe. Juliette Lewis plays Rain with a very Lolita-like air and is a natural for the role (though she was not Allen’s initial choice). Liam Neeson has a great supporting role here too – he is low-key, polite, charming and stuck in the middle of the chaos that surrounds both Sally and Judy.

This film is unlike most in Allen’s canon of films and that is part of the reason I find it such a great watch. He doesn’t stray from familiar ground very often, so when he does, I am excited for the freshness of it all. Sometimes it doesn’t work. Sometimes, as in this instance, it certainly does.

4. HANNAH AND HER SISTERS (1986)

Woody has said that he was re-reading Tolstoy’s “Anna Karenina” and was inspired to write this marvelous, enjoyable film. The film spans one full year, opening on Thanksgiving Day and closes at a dinner party on the very same day. I know Woody always manages to recruit an all-star cast, but of all his films, this one feels most like an ensemble film, with no one really taking the lead, but everyone playing an integral role in the story – and doing a damn fine job of it as well (including Michael Caine and Dianne Weist who each won a Supporting Actor Oscar for their respective roles here). Caine is amusing as the conflicted & unscrupulous Elliot, who cheats on his wife – with her sister Lee (Barabara Hershey) who he is absolutely crazy for and woos with the same gusto as a high school sophomore. Weist is out of control and steals every scene she is in – she is dangerous on the outside, but vulnerable and insecure beneath. Mia Farrow does a fine job as Hannah — the glue that holds the cast together. Max Von Sydow plays the reclusive Frederick and it is great to see him here working with Woody, who is an unabashed Ingmar Bergman fan, so that comes full circle. Von Sydow’s scene with his lover Lee is one of the films highlights. If any character is the outsider here, it is Woody himself. He plays Hannah’s (Mia Farrow) ex-husband, Mickey. They are on friendly terms. Mickey impulsively quits his job to find out what the meaning of life is after he realizes that he is not dying of a brain tumor – a theme that occurs repeatedly in the Allen oeuvre. Unlike most of Allen’s films, this one has a rather upbeat, optimistic ending that goes along with the Thanksgiving Day spirit that the film ends with. Allen explores the topics of religion/faith, love, family, and adultery (as always), but it doesn’t get very heavy as in some of his other films…this one seems more light, more airy – with great music and great one-liners (“And Nietzsche, with his theory of eternal recurrence. He said that the life we lived we’re gonna live over again the exact same way for eternity. Great. That means I’ll have to sit through the Ice Capades again.”) For someone who is not familiar with the work of Woody Allen or told me they weren’t crazy about him, this is the first film I would show him/her – it’s that much of a crowd pleaser.

3. MANHATTAN (1979)

Gorgeous to watch from the very beginning in its glorious black-and-white photography set to the music of George Gershwin. Woody is the consummate New York film director…always has been. The sights, sounds and beauty of New York City resonate in his films. This one may be the hallmark of all that. This was Woody’s first film shot using the widescreen anamorphic Panavision process and he disliked the work here so much that he offered to direct another picture for United Artists for free if they just shelved this one permanently. Thank God they didn’t listen to him, as this one ranks right up there with Woody’s best films. Made just two years after “Annie Hall,” we are again treated to the wonderful on-screen chemistry of Allen and Keaton. Isaac (Allen) is experiencing a mid-life crisis and has been dating Tracy (Mariel Hemingway), who is still in high school. He knows that the relationship can’t progress much further and he is embarrassed to take her out in the professional public. Perhaps she is the safe choice to roll around with after taking a beating from his ex-wife turned lesbian Jill (Meryl Streep) who is in the midst of writing a tell-all book about her marriage to the narcissistic Isaac (“I came here to strangle you!” Isaac barks at her). He meets Mary (Keaton) and is immediately smitten. Mary is dating Isaac’s best friend Yale (Michael Murphy). But Yale is married and is never going to leave his wife. Yale gives his Isaac permission to take his mistress out. Isaac does so and immediately falls head over heels in love with her, ditching the sweet-natured, lovable, and loyal Tracy. But – is this the right decision? Streep is terrific as the ex-wife – strong, quick-witted and bitter. Hemingway makes a perfect Tracey and we absolutely want to comfort her when Isaac gives her the bad news or when he patronizes her with her age throughout. Murphy is a great counterpart to Woody here and we can’t stand him for being such a bad friend. Diane Keaton sheds the Annie Hall aura and plays the cerebral, self-confident and urbane Mary. She does a marvelous job and as always, is a delight to watch. A classic Woody scene comes when he is sprawled out on the couch alone, speaking into his tape recorder and answering the question “Why is life worth living?” Uproariously funny, and at times, quite touching, this is a wonderful love letter to the city the filmmaker loves and a picture to relish in with each and every viewing.

2. ANNIE HALL (1977)

A staple in the annals of film history, “Annie Hall” is one of the great films in motion picture history. Period. Ironically, it is viewed as one of the greatest comedies ever made, but the film was indeed a major turning point for Allen as a filmmaker, as it instilled so much drama and serious themes that he had not yet delved into. Diane Keaton (as Annie Hall) created one of the silver screen’s most memorable and beloved characters ever here…she was without a doubt, the perfect yin to Woody’s yang. To this day, she remains one of my most favorite actresses simply because of her portrayal of Annie. What can I say? I love her! Here, she is flaky, quirky, lovable, sweet, innocent, strong and funny. The hat, the tie, that vest? Lah-di-Dah, Lah-di-Dah…She’s a dream. And I cannot get enough of Woody’s Alvy Singer. I love his reactions to things around him, his disgust at others, his paranoia, his egotism…and of course, his revulsion to any and all things on the West Coast. The chemistry between the two (dating back to “Sleeper” and “Love and Death”) is one of film’s greatest duos – not to be overlooked by other classic onscreen couples. And here, everything that happens (big and small) between the two is just so real – things every couple goes through (click on the poignant and comical “Spider in the Bathroom” scene below and you’ll understand exactly what I mean here). Again, some wonderful one-liners (“That’s ok…we can walk to the curb from here”), great characters, terrific performances (Colleen Dewhurst, a doting Carol Kane, a suicidal Christopher Walken, a pretentious Shelley Duvall)…winner of the Oscar for Best Picture of 1977, it deserves every bit of acclaim it has ever received. I can watch it anytime and have seen it more times than I care to admit. At its core, it is a typical New York love story: boy meets girl, boy and girl fall in love, boy and girl realize that they are “a dead shark” and break up. It doesn’t sound like much – but with the phenomenally woven script, the delicate direction and our two lead actors – it is one of cinema’s greatest films ever.

1. CRIMES AND MISDEMEANORS (1989)

To date, this is Woody Allen’s masterpiece. A perfect fusion of old-style Woody comedy (Woody’s plot line) and Bergman-esque calamity (Martin Landau’s story). Obviously inspired by the seminal themes of Dostoyevsky’s “Crime and Punishment,” Woody would later re-visit these same themes in his latter films with much less of an impact. Here, it is done perfectly. Martin Landau is sensational as the married man (a highly respected opthalmologist) who gives in to temptation (Angelica Huston, who plays her character with such desperation, we can’t help but empathize with her) and then wants the easy out. Alan Alda is deliciously snooty and patronizing as Woody’s brother-in-law and Sam Waterston as the blind rabbi brings a “moral structure” to the narrative. There are some classic Woody one-liners here, some profound symbolism sprinkled throughout and it all is woven together so beautifully when Woody and Landau meet one another near the very end of the film.

Woody here plays his classic loser character making documentary films that no one wants to see – and his scenes with Joanna Gleason and Alda are filled with timeless dialogue. He agrees to make a documentary of Alda’s character in order to pay for the much smaller documentary on spirituality he is trying to make. In the process, he falls in love with the TV producer (Mia Farrow), but he’s already in a marriage with a wife who can’t stand him anymore — plus, Alda’s character wants her for himself! Woody has always grappled with the heavy themes of faith in God, truth, deception, love and betrayal, redemption and forgiveness — but he has never done so in such an intense and insightful manner than he does right here. Hysterical and haunting at the same time, “Crimes and Misdemeanors” is a modern-day classic film of the highest order. Woody truly outdid himself here.

THE BOTTOM FIVE (or “Ones To Stay Away From”)

1. Anything Else (2003)
2. Celebrity (1998)
3. The Curse of the Jade Scorpion (2001)
4. Scoop (2006)
5. Shadows and Fog (1991)