You can keep your roses and chocolates. For the truly miserable, there’s only one thing for it on Valentine’s day – sit down (alone) in the dark and watch a classic breakup movie to remind yourself of all the strife and pain you’ve avoided thanks to your (definitely voluntary) singledom. One of these might just do the trick – welcome to ORWAV’s seasonal list of the Top 10 breakup films of all time! At a time when restaurants are packed to the rafters with smug loving couples, and you have to brace yourself for the yearly questioning from your nan about why you’ve not found someone nice to settle down with, ORWAV are more than happy to provide this valuable public service – don’t say we never do anything for you. So sit back, get your hankies ready, and prepare for some emotional turmoil.

10. (500) Days of Summer (2009)

Courtesy of: Fox Searchlight Pictures

Let’s get this one out of the way early – loved by many, loathed by some, 500 Days‘ occasionally overbearing tweeness is more often than not overpowered by its deceptively dark heart. On the surface, Zooey Deschanel’s Summer is perhaps the culmination of every “Manic-Pixie-Dream-Girl” cliché to come out of the male wish-fulfilment relationship fantasy subgenre – however this convention is flipped on its head in smart fashion by Neustadter and Weber’s perceptive script. For every moment where Summer appears to be everything protagonist Tom (a gratingly idealistic yet relatably flawed Gordon-Levitt) wants in a woman, there are many more when she is stubborn, indecisive and vague – i.e. a real person, instead of the perfect woman he has unfairly made her out to be. Anyone who sees Tom as a heroic and wronged white knight needs to give 500 Days another watch, as it questions notions of what we should realistically expect out of a partner and the existence of the concept of soulmates. It’s not all heartbreak and misery, though – JGL’s dance scene to Hall and Oates’ ‘You Make My Dreams Come True’ remains an absolute treat to this day.

9. Swingers (1996)

Courtesy of: Miramax

Don’t be fooled by the presence of Vince “Dodgeball” Vaughn – this is no frat-pack comedy. Written by and starring the now very successful Jon Favreau (Iron Man, Elf) and shot on a shoestring budget by Doug Liman (Edge of Tomorrow), Swingers is an ode to the power of loyalty and friendship to dig people out of their often self-dug pits of despair after a breakup. Favreau is Mike, a struggling actor freshly out of a six-year relationship in NYC and into an unsuccessful acting career in Hollywood. Whilst Mike is determined to wallow in self pity, his douchey but sincere pal Trent (a charismatic young Vince Vaughn) attempts to drag him out of it by giving him some warped but heartfelt advice and showing him the glorious, seedy benefits of being single in Tinseltown. As much a comedy as a genuine look at heartbreak, the laughs come thick and fast in Swingers as we see the initially inept Mike gradually learn to enjoy his life again in the company of his awful but hilarious friends. More than most, the power of Swingers as a drama derives from its ability to show us that hope for the future is possible no matter how bereft we may feel in the moment.

8. High Fidelity (2000)

Courtesy of: Buena Vista Pictures

Featuring the “King of Indie Heartache” John Cusack and a star-making turn from an unhinged Jack BlackHigh Fidelity is the story of a bitter breakup as filtered through melancholy music and its miserable lyrics. Having relocated Nick Hornby’s 1995 novel from London to Chicago, High Fidelity details the post breakup malaise and self re-evaluation of Cusack’s Rob, an emotionally stunted manchild more at home among his mixtapes and “Top Five” musical lists than with interacting with real people (not at all like this writer, then). As much a love letter to the power of music to create and support relationships as it is a damning portrait of its ability to arrest emotional development and growth, High Fidelity is unafraid of making its hero look like a self-pitying asshole as he lurches from one poorly thought-out interaction to the next. As one might expect from a film so centred around music, the carefully curated soundtrack is wonderfully eclectic and (for the most part) morose as hell – The Velvet Underground, Bob Dylan and Elvis Costello feature heavily as we are asked whether people listen to pop music because they’re miserable, or if they’re miserable because they listen to pop music.

7. The Way We Were (1973)

Courtesy of: Columbia Pictures

Perhaps the most epic and sweeping of the films on this list, the double Oscar-winning, Sirkian romance The Way We Were loses absolutely none of its emotional potency through its grand, historic and political scale. Centring as it does on the Hollywood Blacklist and the paranoid, unjust censorship from the House “Un-American Activities” Committee, to watch The Way We Were now is strangely timely – what with similarly-themed fare like Trumbo and Hail, Caesar! currently hitting cinemas. With a pair of terrific and honest performances from Barbra Streisand and Robert Redford, The Way We Were is about the undeniable attraction that can open up between two people despite some seemingly insurmountable differences – and then the tacit acknowledgement that these differences, despite the love between the pair, simply make things too difficult to be worth fighting past. Its perfect ending as the pair maturely recognise the impossibility of their partnership remains one of the most bittersweet and mutually understanding breakups in cinematic history.

6. Forgetting Sarah Marshall (2008)


Courtesy of: Universal Pictures

There’s a reason Forgetting Sarah Marshall has retained such a strong fanbase nearly eight years after its release, where so many other Apatow-stable comedies have been Forgotten (whey!) – it’s a damn fine film and a valuable take on the post breakup healing process. Equal parts funny, poignant and warm, Sarah Marshall takes a comedically-focused but never less than heartfelt look at Peter’s (Segel, also the film’s writer) attempts to get over a particularly damaging breakup – by accidentally stalking his titular ex to a paradisical Hawaiian getaway (“What are you doing here?” “I came here to murder you! Hahaha…”). The ace up Sarah Marshall‘s sleeve is its rewatchability – the beautiful island setting, perfect cast and the sheer volume of quotable lines make it a tremendously pleasurable piece of emotional escapism. Despite the consistent hilarity (mainly through the deft writing and line delivery rather than any obvious gags), Peter’s broken heart is never far from the forefront, as his heart-to-heart discussions with the resort’s cast of eccentric guests give him the opportunity to alternately vent about and attempt to forget Sarah. Highlights include the brilliantly demented semi-improv balladry from Segel, a surprisingly good Russell Brand and Paul Rudd’s lovably dense surf instructor.

5. Kramer vs. Kramer (1979)

Courtesy of: Columbia Pictures

Often breakups, particularly those between divorcing parents, harm those other than the warring couple – it is with the collateral emotional damage caused in the son of a divorced couple that Kramer vs. Kramer finds much of its societal commentary and power. The winner of five Oscars, Kramer concerns itself with the messy divorce between Ted and Joanna (an obviously top-form Hoffman and Streep) and the subsequent battle between them for the custody of their son Billy. Not one to watch on a date night, Kramer is unflinching in its portrayal of the damage caused to a relationship in turmoil as two of the all time acting greats, both at their peak, trade barbs and threats. However despite the near-constant simmering level of conflict, the screen almost aches with the time they’ve spent together and what could (and possibly should) have been between the pair, as we truly get a sense of what Ted and Joanna once saw in each other. To top it off, Kramer ends with what is surely one of the most iconic final lines ever delivered, in a scene laden with emotional duality.

4. Blue is the Warmest Colour (2013)

Courtesy of: Sundance Selects

Abdellatif Kechiche’s Palme d’Or-winning romance fits the structural pattern of your basic relationship drama – they meet, they fall in love, then A) they live happily ever after or B) it all goes horribly wrong. BITWC falls in the latter camp, but it’s about there that any comparisons with conventionalism end. At three hours long, viewers are put through the emotional wringer as the fiesty, inexperienced Adèle (Exarchopoulos) has her heart slowly built up then inexorably torn down by her new lover Emma (Léa Seydoux). One of the more exhausting and gut-wrenching cinematic experiences available as far as human relationships go, the fact that the pair actually split on fairly amicable terms is of little consolation as we see just how distraught Adèle is throughout the devastating initial breakup scene. Emma’s kind departing words – “I have infinite tenderness for you. I always will. All my life long” – serve only to make Adèle feel all the more wretched. The central pair give towering performances, and BITWC‘s staying power makes it one of the finest and most naturalistic portrayals of a relationship breaking down – lesbian or otherwise – ever committed to screen.

3. Blue Valentine (2010)

Courtesy of: The Weinstein Company

Whilst we’re on a roll with emotionally draining tear-jerkers with Blue in the title, what better time to revisit Derek Cianfrance’s dark, grim and intense story of a marriage in decay? (N.B. Things get a bit cheerier with the next entry, we promise). Michelle Williams (deservedly Oscar-nominated for the role) and Ryan Gosling (criminally not) star as Cindy and Dean, a couple who know that their days of marital bliss are over, but are at a crossroads where they must decide what they should do to give the best chance in life for their infant daughter. Bleak throughout, Blue Valentine‘s audience will cringe as they see both characters make horrendous errors and terrible lapses in judgement as we see that these people simply shouldn’t be together – responsible, giving and caring people apart, when together they become utterly destructive of both themselves and each other. The up and down story of their relationship, marriage and eventual breakup is told in a series of flashbacks and forwards, in which the sweetness of their early days is horribly juxtaposed with the crushing desperation and misery of the final ones. A final, mostly improvised scene as the pair are finally worn down to their very cores sees some powerhouse acting from Williams and Gosling, and is absolutely brutal viewing. It’s got a lovely, Grizzly Bear-led soundtrack, though.

2. Annie Hall (1977)

Courtesy of: United Artists

We told you there would be a bit of levity. Winner of four Oscars and arguably Woody Allen’s finest work, Annie Hall is considered an all-time classic by most and is a rare example of a (mostly) comedy that was able to break through various awards bodies’ long-held and inherent bias against the genre. Allen himself and Diane Keaton play the central couple, with Allen’s Alvy Singer (the most chemically pure example of a Woody Allen hero) meeting, falling in – and subsequently out of – love with Keaton’s titular Annie, in a relationship whose realism remains the standard against which all other film relationships must be compared. It’s the capturing of the little things that makes Annie Hall such a true depiction of cohabitation – the lobsters, the arguments over nothing, the spider killing, the alternately subtle and obvious overtures of pre-relationship flirtation – the list goes on. Undoubtedly just Allen’s views filtered though various characters (one of whom is essentially himself), Alvy and Annie’s dialogues on the nature of love and relationships remain absolutely perceptive and true, and their influence can be seen in romantic comedies – hell, most romances or comedies full stop – right up to the present day.

1. Eternal Sunshine of the Spotless Mind (2004)

Courtesy of: Focus Features

If you could totally erase the painful memories of a former loved one entirely from your life, would you do it? Here it is: Charlie Kaufman and Michel Gondry’s cerebrally challenging, morally intriguing and emotionally rich masterpiece is ORWAV’s number one break-up movie of all time. Fusing sci-fi, romance, and a career-peak Jim Carrey with a twisting, nonlinear narrative and some fascinating philosophical quandaries, the infinitely re-watchable Eternal Sunshine is considered amongst the finest films of any genre since the turn of the millennium – and with good reason. Kaufman’s typically strange, daring and immensely imaginative writing is matched blow-for-blow by Gondry’s equally bold and visionary direction in a perfect marriage of script, ideas and pure visual invention. Clementine (Kate Winslet, terrific) and Joel (Carrey; not even slightly annoying) meet on a beach in Montauk – a place they both feel inexplicably drawn to – and immediately hit it off. What follows, as we soon realise that they have met (and even loved each other) before, poses questions to us about fate vs. determinism, the nature of both love and memory, and whether having emotionally devastating memories of someone we once loved is better than having no memories of them whatsoever. Is it really better to have loved and lost than never to have loved at all? Happy Valentine’s everybody!

And there we have it, ORWAV’s special Valentine’s list of breakup films. What did we miss? 45 Years barely missed out by virtue of the need to give it a year or two to see where it figures in the break-up canon. Multiple other John Cusack films were considered. William Wyler’s Wuthering Heights deserves a mention, though sadly misses out due to our (very scientific) qualifications as to what constitutes a break-up film – ditto Jerry Maguire. Let us know what should have been here in the comments, or on Facebook or Twitter.