An Education

Photograph: Allstar/BBC Films/Sportsphoto Ltd

I watched An Education right as I was entering college while also developing an interest in cinema, and I found it to be such a beautiful, disturbing and devastating film that spoke to a lot of what I was feeling at the time. It tells the story of 16-year-old Jenny being dazzled by the 30-something David, who deftly tricks Jenny into believing he’s a single and honorable man through increasingly lavish gifts. The director Lone Scherfig and the writer Nick Hornby delicately explore many of the issues in play, from David’s predatory actions, to issues of class, to the changing roles and expectations of women during the 1960s.

An Education is well done because it’s a breakup film on several levels: between Jenny and her family, Jenny and David, and then Jenny and the person she believes she wants to be. College is difficult and frustrating, and coming from suburbia, Jenny sees her future as uncertain and dark. David, with his trips to Paris and sophisticated friends, embodies an easy out for Jenny, so she abandons all other relationships and drops out of school for him. As a child, she doesn’t notice until it’s almost too late that David is an emotionally stunted manchild, a negligent father, and a con artist to boot. It’s such a heartbreaking discovery to watch, and was all the more painful to see as a teen still trying to figure out what I wanted to do with my life.

Many tears are shed, but ultimately I love An Education because it’s an uplifting film: Jenny redoes her last year, goes to Oxford and ultimately is able to look back on her time with that creepy man as educational rather than traumatizing. GS

(500) Days of Summer

The relationship comedy-drama (500) Days of Summer, starring Zooey Deschanel and Joseph Gordon-Levitt, is a breakup story with something of Nick Hornby or Woody Allen, told out of narrative order by the lovelorn Tom (Levitt), as he obsessively recounts the various 500 days of his failed, unhappy relationship with a beautiful young woman called Summer (Deschanel). It was an original script by Scott Neustadter and Michael Weber, who went on to adapt The Fault In Our Stars. Looking back, I see that I didn’t like it too much at the time.

But I’ve found myself semi-accidentally and then deliberately catching it on TV over the years, and I’ve seen how ungenerous I was. It is a really fervent, and even devastating story of male heartbreak, encapsulated by the now legendary “split-screen” sequence showing Tom’s Expectations versus Reality, as he shows up to a post-breakup party thrown by Summer. On the left side of the screen, we see his fantasies that their old magic will somehow kick in and they will get back together, on the right, we see the agonising reality of her distant, polite greetings to someone who is now in the friend zone. These scenes unfold in parallel and then gradually diverge in a way which is excruciating. I can’t believe there is anyone who hasn’t hopefully, pathetically shown up to a party to which they have been diplomatically invited by someone who’s dumped them – invited, in fact, with the specific purpose of subsuming them back into the platonic category of “friendship”. But the rejectee will always agonisingly hope-against-hope that something might still happen. 500 Days Of Summer isn’t a masterpiece but it’s got the authentic vinegar taste of male romantic sadness. My one quarrel is that the woman with whom Tom then finds happiness is called Autumn. Surely that should be Spring? PB

Happy Together

Photograph: Moviestore Collection Ltd/Alamy

The films of Wong Kar-wai are made out of sighs; the contented swoon of a new infatuation, the panting gasp of overheating pleasure, the defeated exhalation that’s all one can manage when an emotional weight is pressing down on their chest. His cinema understands all expressions of passion, whether filtered through love or lust or pain, to come from the same naked need for human connection. My favorite work from the Chinese master focuses on a corollary idea, that the vulnerability required of that connection can make us guarded, which in turn perverts affection into vindictiveness and trust into self-destructive obsession. Wong makes the daring suggestion, a conclusion far too uncommon in western romance films, that breaking up can be its own gesture of devotion.

A gay couple (Leslie Cheung and Tony Leung Chiu-wai, the latter delivering what is in this writer’s opinion one of the greatest performances ever committed to celluloid) go to Buenos Aires to break up their toxic on-again-off-again routine, only to split without enough money to return to Asia. Their ensuing attempts to build lives separate of one another, many of them failed, clarify the unique terms of a relationship that thrives on dysfunction and recreational cruelty. The same things keeping them together – a codependency bridging the gap between neediness and the need to be needed – make it impossible for them to last. And with ravishing colors courtesy of the cinematographer Christopher Doyle, the lush Argentinian scenery refracts their overgrown, untamed feelings back at them. CB

Brokeback Mountain

I didn’t watch Brokeback Mountain as an emerging-from-the-closet teenager, even though it felt like required viewing. I was interested in “edgier” stuff at the time (like Maurice and Y Tu Mamá También) and thought the film would be overly sentimental. Thank God I held off. Because Brokeback Mountain is a film best appreciated by those familiar with heartbreak.

I watched it for the first time last year, in my mid-twenties, and found myself deeply moved by the star-crossed-lovers and their poignant breakup because, even while hurling curse words and threats at each other, the two men are still in love. “We could’ve had a real good life together,” Jack shouts at the top of his lungs, his lips quivering. “Had a place of our own.”

I love the grounded specificity of Jack’s “happily-ever-after.” How – in the midst of calling it quits – Jack paints a world where he and Ennis have a ranch and live in domestic bliss. As a queer person, I can easily connect with this kind of fantasy-building. Imagining how easier life would be if the pressures of society weren’t so great.

Brokeback Mountain is a product of its time. Hollywood’s queer representation skewed towards melancholy back then – a reflection of the scant rights and protections the LGBTQ community had in America. Today, queer cinema is finally beginning to provide some happy endings (think: Love, Simon and God’s Own Country). Which is important for a slew of reasons. But I like to watch Brokeback Mountain every now and then when I need a reminder that, not too long ago, our love stories too often ended in heartbreak. AW

The War of the Roses

Photograph: Moviestore/REX Shutterstock

At the tail end of 1989, mere weeks away from a new decade, audiences were gifted with an unusual Christmas present: the violent, foul-mouthed destruction of a much-loved movie couple. In hit screwball adventures Romancing the Stone and Jewel of the Nile, Kathleen Turner and Michael Douglas quipped and kissed their way in and and out of PG-level jeopardy but in The War of the Roses, the danger wasn’t in the jungle or the desert but it was in the home and, most disturbingly, in each other.

It’s a relentlessly, audaciously nasty little film wrapped up in glossy packaging with a deceptively sprightly score, fooling you into briefly forgetting just how mean-spirited the whole thing is. We’re shown how an annoyingly perfect, somewhat smug, married couple is torn apart, not by infidelity or abuse, but by growing, seething resentment which finally boils to the surface in the most hysterically, horribly funny manner. After Douglas’ preening lawyer survives what he thinks is a heart attack, Turner’s exhausted housewife tells him the whole debacle made her imagine what life would be like with him dead and, to his disgust, it made her feel happy and free. She tells him: “When I watch you eat. When I see you asleep. When I look at you lately, I just want to smash your face in.” He dares her to do it. She does. And then the gloves are really off.

He destroys her shoes, she locks him in the sauna, he pisses on her food, she ruins his car and they continue to verbally and physically abuse each other until a final brutal showdown ending with them both dead after falling from a chandelier mid-fight. For a moment, we’re fooled into thinking the film is softening as a dying husband lays a hand on his dying wife but as the music swells and we think she’s reaching to hold him back, instead she pushes it off. It remains one of the most staggeringly sour endings to a studio comedy I’ve ever seen and one that I can’t even imagine making it to the big screen now.

For me, the single, never-married product of divorced parents, there’s always been something grimly compelling about watching a marriage fall apart on such a grandiose and grotesque stage, no holds barred, played for sadistic laughs. Maybe it’s the savage, if exaggerated, honesty of it I always admired, that underneath the civility of married life, there are two people quietly waiting to piss all over the other one’s dinner. BL

Like Crazy

Photograph: Moviestore/REX/Shutterstock

Like Crazy documents the mostly long-distance love between Anna (Felicity Jones) and Jacob (Anton Yelchin) that withers under the pressures of time and 6,000 miles (Jacob based in LA, Anna confined by an overstayed visa to the UK). While doing press for the film, the director Drake Doremus said the actors were given an emotional outline of the characters, and the actors filled the rest in, improvising how they’d imagine their characters would fall in love, then fall apart. I can count on my fingers the number of movies that have made me actually cry, and perhaps this is why Like Crazy is one of them: it captures exactly the spontaneity of a relationship’s growth and decay – in particular, the magnetic pull of phone as a portal both treasured and loathed, the gap between where your mind is and where you are, the realization that someone’s life has gone on without you. (It did not help that I watched it in light of Yelchin’s devastating accidental death at age 27).

At the end, Anna and Jacob stand together in the shower, embracing, finally getting what they wanted only to doubt that want in the first place. They look at each other and say nothing, but I heard: you don’t know this person anymore. Maybe you never really did. It’s not a breakup scene, per se, but their unguardedness is broken. The last shot lingers on Jacob’s face in the shower, haunted not by Anna’s absence but her presence, and processing one of the most unsettling experiences I know – the feeling of your old certainty about someone crumbling into doubt, and realizing your own sparks can fade. AH

Le Chat

The breakups that break my heart are the ones that don’t involve a break at all. No dramatic exits, just the misery of a relationship’s long-drawn-out demise. That’s the painful case in Pierre Granier-Deferre’s melancholic 1971 movie Le Chat. It stars two magnificent actors: Simone Signoret and Jean Gabin, who would have made a sizzling on-screen couple once, smouldering across the age-gap. Here, in a film made towards the end of both their careers, they give electric performances as people trapped in a relationship that has run out of love. Married for more than 25 years and now retired, they live separately but together, sharing a house in a city district that is being razed for redevelopment. Nothing stands around here but their funny little home, just as nothing exists of their marriage but their shared address.

Perhaps they were always an unlikely pair, a typesetter and a circus star, but once upon a time in a flashback Julien and Clémence loved each other. And then one day he didn’t any more, so now Clémence is miserable. They’re cruel to each other, in petty ways, and sometimes she drinks too much and flies into a rage, but otherwise they pass their days eating, reading and sleeping in each other’s stifling presence, in a bitter silence made up of all the sentences left unsaid – words of recrimination or regret, or “I’m leaving” and “Don’t go”. The only messages that get through are notes on scraps of paper, like the one passed day after day from Julien to Clémence that reads: “Le chat?”. Because if it’s awful enough to watch these two people suffering, it’s nothing to what happens to Julien’s poor cat. PH

Starship Troopers

Photograph: Alamy

I can’t say I’m a particular fan of movie breakups: they’re miserable enough to endure in real life without having to see them projected on the big screen. But I always admired the way Denise Richards dumped Casper Van Dien in Starship Troopers – via interplanetary video message, the sci-fi equivalent of Daniel Day Lewis’ fax to Isabelle Adjani.

Recollect the scene, if you will. Casper – or Johnny Rico, as this blond alpha male is called – receives a much anticipated missive from the lovely Carmen; she, being a thousand times smarter than him, is on her way to becoming a military pilot, while he is stuck with the grunts in the infantry. So, while all Rico’s squadmates are leering over his shoulder, Carmen gives him the old dagger in the heart: “I’m gonna go career”. Her job comes first. That’s one in the eye for the perfectly-chiselled schlub.

But this breakup is a bit more than simple teen-movie trauma. Starship Troopers is one of the all time great satires, and this is just part of it. Johnny Rico, the Buenos Aires-dwelling ubermensch, might be a superman on the football field but outside school he’s the opposite of a high flyer. Getting dumped by Carmen is just the start: he messes up his command, gets mercilessly flogged and is reported dead after a disastrous mission against the alien Bugs. Carmen’s progress is equally questionable: she makes the grade professionally, but the man she dumped Rico for gets his brains sucked out by a revolting giant insect in front of her. You win some, you lose some. AP

Blue is the Warmest Color

Photograph: Publicity image from film company

Have there ever been quite so many tears in an on-screen breakup before? “Tears” is putting it delicately, in fact. Really, it’s the streams of snot running down the blotchy, swollen face of then-19-year-old actor Adele Exarchopoulos that give the climactic separation in Abdellatif Kechiche’s three-hour lesbian coming-of-age romance a particular kind of brutal, wrenching authenticity.

Nobody cries prettily in a breakup; rare is the film that admits as much. Still, the stakes in this breakup are higher than most. Radiant blue-haired artist Emma (Lea Seydoux) hasn’t just been Adele’s first girlfriend, but her guide into a new sexuality and a new self, from teenage uncertainty into assured womanhood: her memories of life before Emma are memories of another life entirely, one she never wants back. That kind of severance more than merits a bit of snot.

But it gets better, as these things tend to do. Kechiche lingers on his film’s exquisite post-breakup coda, showing how lives are rebuilt around the scar of an ended relationship, even if the pain never entirely goes away. We see Adele and Emma meet again twice, amicably but awkwardly. In a cafe, hopes for a reunion are dashed by Emma’s announcement of her new, less sexually fulfilling relationship; later, at an exhibition of Emma’s paintings, Adele spots a large nude of herself and leaves, as if finally assured that she’s left something of herself behind. Emma will always have “infinite tenderness for her”, she says, but Kechiche’s intimate epic understands that recovering from a breakup is mostly about mending the split within yourself. GL

Casablanca

Much like when the kids say “bad” they mean “good,” when Humphrey Bogart says “I’m no good at being noble” what he means is “stand back, world, I’m about to be extremely good at being noble.”

Hollywood lore tells us that Casablanca was well into production before the last scene was written. A “happy” ending where Rick Blaine (Humphrey Bogart) and Ilsa Lund (Ingrid Bergman) end up together was considered, but that would also mean Victor Laszlo (Paul Henreid) ended up dead or at least without “the thing that keeps him going” (eg Ilsa) and, thus, unable to lead the fight against Nazism. No, Rick and Ilsa can’t stay together, because “the problems of three little people don’t amount to a hill of beans in this crazy world”.

What’s strange, though, is no matter how many times I’ve seen the film (and it’s got to be over 30 by now) I still weirdly hope that one of those longing glances between Bogart and Bergman will break them out of their fate. Maybe this go round Louis Renault (Claude Raines) will come up with some kind of solution that gets Major Strasser (Conrad Veidt) off everyone’s back, allowing for a moment to think this through like adults. Victor Lazslo isn’t a bad guy; once he sees that being with Rick is what Ilsa wants (what Ilsa needs) he’ll loosen his grip. And yet, every time, she acquiesces to Rick’s martyrdom (“you said I was to do the thinking for us”) and gets on that plane to Lisbon. Luckily, joining a Free French garrison in Brazzaville with Louie ought to keep Rick occupied as he mends his broken heart. JH

Hannah and Her Sisters

Annie Hall is Woody Allen’s great breakup movie. Manhattan his prickliest; Crimes and Misdemeanors the one in which the dumping has the direst fallout. It would have been apt to choose that film for this feature, as Noah Baumbach riffs off it in While We’re Young – plus its fabulously crass turn from Alan Alda, who’s also in Marriage Story.

But I’m going for the Allen film I most frequently revisit, one which is really a series of breakups and hookups, bookended – and sandwich-filled – by three Thanksgiving parties, with plenty of flashbacks for added narrative zip.

The biggest split is the one in which the viewer would assume they’d have the least investment, because you’ve been encouraged to eyeroll at its casualty. Lee (Barbara Hershey, incredibly raw and luminous throughout) has spent her first hotel room afternoon with Elliot, the besotted accountant played by Michael Caine and – unhappily, he says – still married to her sister, Hannah (Mia Farrow). Lee returns to the loft she shares with Frederick (Max von Sydow), an intolerant and intellectually superior artist many years her elder.

He tells her about a Holocaust documentary he’s been watching, in a long monologue von Sydow wholly inhabits, despite it being pure Allen at his most miserablist. Suffocated, Lee says she needs to move out, that that was always inevitable. Frederick guesses the truth – or part of it, at least. And he’s wracked: with grief, with anger at her, and most of all frustration at himself.

It’s two long takes, with one discreet edit. And it’s just virtuosic. The odious snob becomes a sympathetic victim. Lee’s reasons, even without Elliot, are completely sound, yet for the first time, you sense her decision might not be right. Even the most ploddingly obvious breakups can come suddenly; the viewer is slapped with this truth almost as hard as Frederick.

Hannah and Her Sisters is a movie of extraordinarily acute emotional intelligence, especially about female feelings. It’s also one of Allen’s warmest and funniest. This scene is sober, perfect and unshakable. CS