Woody Allen’s Classic Leading Ladies and Their Contemporary Counterparts

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When Freud wrote of female sexuality as “a dark continent,” he might as well have been writing about Woody Allen’s murky understanding of women. The director’s female characters invariably have abundant daddy issues, a slew of neuroses, and affairs with artists, professors, married men. They seek advice from therapists and fortune tellers, they’re tempestuous and stubborn; though they’re sometimes incredibly narrow, they’re often appealingly complex. Allen’s female characters are so obviously amalgamations of his fantasy woman – or rather women, plural – that one might contend they’re part of an ongoing, experiment in understanding women. Following this week’s news that Emma Stone is set to star in the next Allen film, we’ve conducted a little experiment of our own, looking back at the ladies of his canon, matching the women of his classic era with their contemporary counterparts.

The Crazy Ex-Wife

Then: Meryl Streep Now: Penelope Cruz

Meryl Streep’s Oscar-nominated performance as Jill, Isaac’s (Allen) lesbian ex wife in Manhattan, saw her character pen a book containing cringe-worthy details about her former husband’s sexual performance – which apparently helped her learn that she just wasn’t into men. A later Allen film which also experiments – though more playfully – with female sexuality is Vicky Cristina Barcelona, wherein another enraged ex-wife appears. This time, it’s Maria Elena, played by Penelope Cruz, inflamed over her ex-husband Juan Antonio’s (Javier Bardem) affair with American tourists Cristina (Scarlett Johansson) and Vicky (Rebecca Hall). Though playing an angrier (and certainly odder) character, Cruz reminds one fleetingly of Streep in Manhattan: the moment when Maria Elena shoots Vicky in the hand, thinking she is Cristina, perhaps equals Jill’s book stunt.

The Best Friend

Then: Dianne Wiest Now: Rebecca Hall (and Greta Gerwig)

Allen’s “best friend” archetype is the girl who is always getting overshadowed by her louder, and maybe also more attractive, friend. Though she’s whip-smart, she’s always coming up second best. Dianne Wiest played her to perfection in Hannah and Her Sisters. Always a Holly, never a Hannah, Wiest never did get the romantic lead in an Allen picture, but her razor-sharp wit and comic timing make her one of his pithiest actresses. The same applies to Rebecca Hall, who, as Vicky in Vicky Cristina Barcelona, becomes jealous of all the attention Juan Antonio’s giving Cristina. Of course, it can’t be easy being Scarlett Johansson’s best friend. Allen’s latest film, To Rome, With Love, includes a similar dichotomy: Greta Gerwig falls short in her boyfriend Jesse Eisenberg’s eyes when her more interesting (and, it turns out, horrendous) actress friend Ellen Page comes to stay.

The Betrayed Wife

Then: Mia Farrow Now: Rachel McAdams

Doe-eyed Mia Farrow wouldn’t hurt a butterfly in The Purple Rose of Cairo, in which she plays timid housewife Cecilia, living in a drab, depressing New Jersey suburb – in the Depression years, no less – and who lives to go to the movies. While her brutish husband beats her at home, Cecilia is most herself at the movie theater – and with the film character Gil, who (in a touch of magical realism) leaps off the screen and falls in love with her. Farrow went on to play another – too – good wife in Hannah and Her Sisters, in which one of her sisters betrays her by sleeping with her husband.

Much later down Allen’s cinema credits comes his excellent time-traveling film, Midnight in Paris – and with it another betrayed wife. Like Hannah’s, Inez’s (Rachel McAdams) husband is cheating on her (and yes, it still counts if your mistress is in another era), though we’re less sympathetic in this case. Inez is constantly nagging at her nostalgia-ridden husband — also, curiously, named Gil (Owen Wilson) — who wants to move to Paris. But she doesn’t even entertain the idea of her husband’s fantasy, or believe him when he tells her that he’s hung out with Hemingway and the Fitzgeralds (he has). Instead, she would rather cheat with her pretentious old crush Paul (Michael Sheen), in town to teach at the Sorbonne, and act douchey at Versailles, wine tastings, and art galleries.

The Dream Girl

Then: Mariel Hemingway Now: Marion Cotillard

In Midnight in Paris, as Gil falls in love with Adriana (Marion Cotillard) by the Seine of 1920s Paris, he discovers he’s unhappy with his wife Inez and their present-day Hollywood life. In Manhattan, it works the other way around; it’s only after Isaac has left his 17-year-old girlfriend Tracy (Mariel Hemingway) to be with Mary (Diane Keaton) – and once Mary has left him – that he realizes he’s in love with his high-schooler ex. Of course, both these relationships are impossible. But that’s not all these two characters have in common. They’re both meek and pretty, apparently malleable but actually iron-willed. When Adriana resolves to go back to La Belle Époque, retromaniac Gil is left to make do with the present. As for Isaac, besides the fact that a 40-something just shouldn’t be with a 17-year-old, Tracy shows her resolve as she leaves for London to study drama.

The Original: Diane Keaton

When it comes to the leading ladies of Woody Allen’s movies, no one compares to the indomitable Diane Keaton. Sure, Scarlett Johansson seems to crop up in many Woody Allen films, and, yes, Naomi Watts also played quite an endearing character in You Will Meet A Tall Dark Stranger — but let’s face it, they’re no Diane Keaton. To every role she played opposite Allen in his early films, Keaton brought a wit, grace, and intelligence that goes unmatched by her surrogates in the later Allen films. From romantic comedies like Annie Hall and Manhattan, in which she appears as the brainy, beautiful, difficult love interest, to the sillier, frolicsome pictures like Sleeper and Love and Death, where Keaton excels in meeting the tempo of Allen’s slapstick humor, she is the ultimate love interest.