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4. Vicky Cristina Barcelona (2008)

Off the top of my head, I cannot think of a filmmaker who has directed more women to Oscars than Woody Allen. We’ve discussed Wiest and Keaton, but who can forget the memorable, over-the-top performance that yielded Penelope Cruz her Oscar for Vicky Cristina Barcelona? Vicky (a then-unknown Rebecca Hall) and her friend Cristina (who else but ScarJo?) decide to travel to Barcelona for the summer. The two of them are hoping to find inspiration (or, for Cristina only, at first, even love). Vicky is down-to-earth, straight-edged, and engaged. Cristina is the opposite: a free-roaming spirit with few cares other than to get in touch with her emotions. What follows is a hysterical, touching, and, frankly, realistic portrayal of what can happen to American women as they encounter and are immersed in cultures that have a different approach to love and sex than our own.

Presaging what would later become his love affair for foreign cities like in Midnight in Paris, in Vicky Cristina Barcelona, Allen romanticizes (without being trite) the intense passionate way of love that characterizes (without being too stereotypical) Iberian culture. In their travels, Vicky and Cristina encounter the tumultuous, tortured love life of two Barcelona denizens, a sentimental Javier Bardem, and his unhinged ex-wife, played by a stunning Penelope Cruz. What follows is a lesson of self-discovery for both women that will mark them forever. Both are taken out of their comfort zone. Both are left with battle scars that will grow to define them. And Allen is very clear in his lack of endorsement of either woman’s approach to life: Vicky was too uptight, but Cristina was too selfish. In the end, neither model works. And Maria Elena (Cruz’s character) is crazy, but also irresistible. Thus, brilliantly with that triumvirate, Allen once more explores the different ways in which women love and attract love. The men, particularly in this movie, are just along for the ride. On top of all that, he makes witty, on-the-mark observations about the silliness of some Americans’ interaction with foreign cultures.

But what stands out is how different and modern this movie feels compared to some of his others. While in movies like Annie Hall, Allen explores old-school love, the grown-up love of the artistic communities of the time, in Vicky Cristina he reinvents and rediscovers the formula to adapt it to modern times, modern anxieties and desires, and modern approaches to love. All the while, he keeps the same underlying point: love is hard, it’s insanity-inducing, but it is simply too hard to resist.

3. Hannah and her Sisters (1986)

Perhaps his most-critically acclaimed movie after Annie Hall, and the one that netted his second writing Oscar, Hannah and her Sisters is the grown-up version, to me, of Annie Hall. While in Annie Hall the characters are silly, sometimes infuriating, but mostly lovable and irresistible, the characters in Hannah may start out as such, but then are revealed to be at times impossible to sympathize with. The story revolves around Hannah (played by Mia Farrow, in one of her last collaborations with Woody), her husband Elliott (the Oscar-winner Michael Caine), and, obviously, her two sisters. Allen himself is Hannah’s ex-husband, a hypochondriac television writer in yet another true-to-life portrayal of the director.

The story centers on two years in the lives of these complex characters - alcoholics, adulterers, depressives, and self-involved maniacs are the people that inhabit this film. When all is told, however, and for all the pain and suffering that they inflict on each other, many of them end up exactly where they began the film, reconciled, or with no greater answers then when they began. Life rolls along with its punches, Woody is telling us, and every crisis may seem life-or-death, but in the end we are all simply in it together, rolling towards a great unknown, a great nothing that is at the same time everything.

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