List Film

Five of the best cinematic unhappy endings

This Valentine's Day, enjoy some movies where the two leads don't live happily ever after

Five of the best cinematic unhappy endings

1. The Way We Were (1973)

Directed by Sydney Pollack
Politically active and opinionated Katie (Barbra Streisand) falls in love with the most popular boy of the whole college, Hubbell (Robert Redford). They part ways, meeting again once they’ve started their adult lives, and begin a relationship in which Katie feels inappropriate and out of place as her beliefs and ideals are sidelined. Regardless of their problems, it’s heart-warming to see how the pair manage to meet half way for years – which is why it’s so unexpected when Hubbell suddenly decides they are too different and tells Katie he wants to end it (a little unfair, considering she’s pregnant with his child). Watching Katie beg for Hubbell to stay is heartbreaking, as she negates the image of a strong, independent woman we felt admiration for throughout the film. It’s an unhappy ending, but it’s also terribly true that, just because two people are in love with each other, it doesn’t mean things will work out.

2. Annie Hall (1977)

Directed by Woody Allen
93 minutes of delightfully expressed neurosis, in which Alvy (Woody Allen) tries to analyse the flows of his relationship with Annie (Diane Keaton). Hours of therapy for both of them with New York’s finest psychiatrists and a few break ups and make ups count for nothing when Alvy realises Annie just doesn’t want to be with him anymore. The film ends with Alvy’s thoughts on love and relationships, which are very well put and worryingly realistic – in other words, not the happy ending we were all cheering for. In all fairness though, it is Woody Allen and it would be foolish to expect any other ending to this film.

3. My Best Friend’s Wedding (1997)

Directed by PJ Hogan
A romcom in which we find Julienne (Julia Roberts) desperately in love with her best friend – and ex-lover – Michael (Dermot Mulroney), who's about to marry the easily enviable Kim (Cameron Diaz). The audience is encouraged to take Julienne’s side throughout, which makes it extremely disappointing when Michael confounds romcom expectations and marries Kim anyway. Julienne attends the wedding and accepts Kim’s request for her to be a bridesmaid, a detail that makes it all the more unbearable to watch. Luckily, her (maybe) gay best friend, George, played by an irresistible Rupert Everett, surprises Julienne at the wedding reception and softens the ending by bringing an optimistic breeze into the last few minutes.

4. Closer (2004)

Directed by Patrick Marber
The film starts with a very typically romantic encounter between Dan (Jude Law) and Alice (Natalie Portman), to then skip a year of their life which they spend as a couple, and present us with Dan’s first meeting with Anna (Julia Roberts again - what is it with this woman and heartbreak?). The story is a parallel between two relationships made of lies and adultery, in which none of the four characters can be trusted and there is no space for a happy ending. As Anna moves on and marries Larry (Clive Owen) she still keeps seeing Dan, up to the point where they decide to be together and break up with their respective partners. Even then, Anna ends up breaking it off with Dan once again. When Dan goes back to Alice she forgives him, and for a moment the possibility of the two of them working it out seems almost possible – but something is broken and it can’t be fixed. A realistic plot, combined with fantastic acting, but definitely an unhappy ending to a generally unhappy film.

5. One Day (2011)

Directed by Lone Scherfig
The film adaptation of David Nicholls’ novel begins with the unusual first meeting between Emma (Anne Hathaway) and Dexter (Jim Sturgess): a couple who spend the last night of university together without having sex. Throughout their adult lives, they fall in and out of love with other people – Dexter even gets married – but soon after that it becomes obvious to all involved that Emma’s the girl for him. Then, just as it seems like everyone will get what they wanted, Emma is run over by a car and dies, leaving Dexter unable to fully recover, and the viewer in a very similar state of mind. The film ends with Dexter’s flashback on the day they met, as he wonders what could have happened if he had started a relationship with Emma since that very first moment, instead of seeing her as a friend for all those year. It’s a call to live your life according to your passions and savour every detail, or at least look both ways before crossing the road.


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