Woody Allen’s Classic Leading Ladies and Their Contemporary Counterparts

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.

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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.