7. Tracy – Mariel Hemingway in ‘Manhattan’
As the first love interest in a Woody Allen film of startling age difference, and the most affecting in a tradition that would grow increasingly uncomfortable for audiences as the years went on, Tracy is one of the most underrated characters Allen has ever written.
A student far more mature than her years, and infinitely more mature than Woody’s character Isaac, she stands out in the film as the only one with a genuine self-less love, and it’s a heartbreaking thing to witness as she falls upon that sword in this world of shallow neurotics and self-serving adults acting like children.
The breakup scene between her and Isaac in a soda shop, where she gives him the gift of a harmonica, is one of the most painfully accurate moments of romantic divide ever captured, as Isaac, unaware of how much he’s throwing away, leaves Tracy in total emotional meltdown, tears streaming down her face.
6. Pearl – Maureen Stapleton in ‘Interiors’
All at once she is a shrewd device, a breath of life into a dying garden and a character you want to take home with you. In a family of almost suffocating taste and restraint, of homes and decorum strenuously maneuvered to depict cool, upper-class austerity, comes this splash of red paint on a grey surface.
As the new relationship for Arthur (E.G. Marshall) after many years of, his own words, dedication and responsibility, he rather brazenly casts off the shackles of his previous marriage to all-too-perfect Eve and brings this zesty woman to the table.
Gleefully coarse and unapologetic, with tales of prior husbands and card tricks to boot, she gives a sense of what this family has been lacking, and we can see the walls of cold feeling and suppressed emotions starting to come down with her arrival. She is the thawing out so badly needed by this emotionally frozen family.
5. Eve – Geraldine Page in ‘Interiors’
With his next film, Woody focused on a mentally fragile matriarch facing abandonment and total psychological collapse. Although ‘Interiors’ contains other fantastic performances by Diane Keaton, Mary Beth Hurt (especially poignant) and Kristen Griffiths as three sisters, Eve stands as one of Allen’s most uncompromising and disturbing women.
An interior decorator, ironically obsessed with the surfaces and adornments of her surroundings as her inner life withers, Page’s performance is a persuasive depiction of a person on the precipice of sanity. Her face crumples with involuntary tics and her eyes dart in moments of denial. Her voice maintains a hollow, passive-aggressive whine, only allowing it to burst forth in moments of anger and pain, where it is then retracted and locked back into a place of near-ghostly inexpression.
Even as she readies herself for a suicidal gassing in her own home, or marches determinedly towards the churning ocean in a charcoal grey suit, she moves with an ethereal grace, her body being the only thing she can control in her world turned upside down.
4. Annie Hall – Diane Keaton in ‘Annie Hall’
Basically a celebration of Diane Keaton, Annie was a thinly veiled concoction of everything Woody admired about this unique actress, with whom he shared a brief romance and subsequent lifelong friendship.
With a wardrobe of Keaton’s own clothes (a lot of men’s shirts and ties) that became a trend setting style in the wake of the film, this naïve, open-minded, eager to please singer from Chippewa Falls, Wisconsin gets an education in love with Allen’s Alvy Singer, a deeply neurotic, self-obsessed comedian.
In an act of great humility, Allen essentially gives the film to Keaton, allowing his character to be seen as increasingly stifling and hard to live with, as opposed to Annie, whom he urges to expand intellectually and creatively throughout the film.
In the film’s bittersweet conclusion she has eventually outgrown Alvy, seeking more out of life than he can ever provide from his dark, insular viewpoint of the world. This tender and honest approach to romantic comedy (looking at how, sometimes, opposites do not attract in the long run) was revolutionary at the time and paved the way for Allen’s continuous searching for love and meaning in contemporary relationships.
Annie and Alvy are ill-matched from the get-go, but the film captures their isolated moments of true connection with a breathtaking nostalgia (lobsters anyone?) ‘Annie Hall’ struck a chord of realism that people could immediately identify with in their own lives. She remains one of Woody’s most memorable creations, an ode to a spectacular, imminently lovable woman.
3. Holly – Dianne Wiest in ‘Hannah and Her Sisters’
In a filmography ripe with neurotics and self-obsessives, few are painted with such affection and continuous peril as this cocaine-addled black sheep. Whether taking a shot at acting and going through the audition mill, or toiling as one half of the Stanislavsky Catering Company, Holly is on her own path of discovery and desperate to find her true calling.
Dianne Wiest’s Oscar-winning performance is a memorable addition to, and most winning example of, Woody Allen’s female doppelgängers: a panic-stricken soul whose low self-esteem threatens to dash their every attempt but with a saving grace of tenacity, a spark inside, that keeps them going in the face of self-imposed adversity.
In one of Allen’s most hilarious sequences, his Mickey Sachs goes out on an ill-advised date with Holly. They begin at a brash rock concert where Mickey can barely hear their conversation (and which probably hints at the ‘ringing and buzzing’ that leads his character to worry over a possible brain tumor).
They end up at a more laid back piano bar listening to Bobby Short, where coke-fueled Holly can barely keep still at the table, fidgeting like mad amongst the discreet crowd. Their meeting up again a couple years later, and eventual warming to one another, makes for one of Woody’s sweetest story arcs, fueled by Wiest’s klutzy embodiment of a truly imperfect person, written and performed with keen fondness, empathy and intelligence.
2. Sally – Judy Davis in ‘Husbands and Wives’
Enough has been written about the behind the scenes turmoil that fueled ‘Husbands and Wives’ to distract from how truly insightful, if bleak, and momentous a film it is in Woody’s filmography (it’s like Woody Allen’s ‘Rumours’ album), so enough about all that.
The character played by Judy Davis…well, Vincent Canby put it best in his original New York Times review, and he will be quoted here: “Sally must be one of the most endearingly impossible characters Mr. Allen has ever written, and Ms. Davis nearly purloins the film.” So very true. Rarely has there been such a quotable, hilarious, ice-cold and maddening character in Allen’s work, and Davis makes her so watchable and even empathetic (at times).
As a woman who begins the film with the utmost confidence, cavalierly declaring a mutual divorce between her and her husband Jack (Sydney Pollack), we almost immediately begin to see the cracks, her contradictions and her almost savage inability to express warmth.
After a date with Liam Neeson she comments on every single aspect from dinner down to the car ride home with a light passivity and then immediate cutting criticism. In the midst of sex, we hear her running commentary as she tries to relax, eventually turning into an inventory of how her friends and acquaintances are either hedgehogs or foxes.
And in one of Allen’s most painfully hilarious scenes, she ends up screaming down a seemingly pleasant new beau over alleged sexism ‘Don’t defend your sex! You’re great ‘till you start to show your age, then they want a newer model!’
The character of Sally digs deep down into that fine line that separates men from women, and makes women sometimes impossible for men to understand. Davis’ Oscar nominated performance is a wonder to behold, somehow imbuing this sporadically aloof woman with an underlying helplessness. Sally is a terror and a beauty all at once.
1. Jasmine – Cate Blanchett in ‘Blue Jasmine’
Sweeping into San Francisco from New York with Louis Vuitton bags in tow, thirsty for a Stoli martini and ready to tell her tale to anyone within ear shot, Jasmine is memorable from the word go and her ability to fascinate audiences diminishes not one moment after we meet her.
Even though fallen on hard times, she holds onto her style with a stranglehold, her accoutrements now a buoy in an ever rising tide of desperation and mediocrity.
Allen has depicted more than his fair share of women in crackup (and those characters have become a primal embodiment of his own neurotic tics and obsessions) but Jasmine stands apart from them and is somehow their reigning queen, rubbed raw and driven to the edges of hysteria not because of passion, jealousy or existential nihilism, but out of sheer terror for a very real, impending future – one which she may have had a hand in creating herself.
She’s one of Woody’s sharpest critiques yet, a specimen of a division of society unable to exist without the amniotic bubble of abundant currency or stultifying creature comforts. Out of his many women Allen has created, in Jasmine, one who walks a perilously fine line between victim and villain, unwilling to make it easy for us to assign blame or fully sympathize.