The 10 Saddest Films of the Last 10 Years

Given how skewed the list is towards films from before 2020, I’ve either gotten more cynical in my old age or the films being made have gotten less heart-wrenching. Whatever the case, 2016 offered three very different films that each left me in a puddle of tears.

The first is Barry Jenkins’ Moonlight, a genuine modern classic (one that fans of early A24 like Room and American Honey will adore) and the first openly queer love story to win Best Picture at the Academy Awards. The story takes place in three acts, each from a pivotal time in the protagonist’s life: his formative adolescence with an unlikely father figure, a teenage moment that suggests a queer awakening, and a later acceptance of that pent-up longing. I’m already welling up just thinking about it. 

The next great 2016 tearjerker that comes immediately to mind is Kelly Reichardt’s portmanteau film Certain Women, and specifically the middle third, which features another story of unrealised love (I’m already starting to see a pattern). This one boasts a wonderful performance from Kristen Stewart as an anxious night class teacher, but it’s Lily Gladstone (playing a student with an evident crush) who steals the show.

This was Gladstone's breakout performance and is still (IMHO) her finest work, so if you loved her in films like The Wedding Banquet and Killers of the Flower Moon, you owe it to yourself to check this out. 

You probably don’t need reminding about this one, but Kenneth Lonnergan’s Manchester by the Sea is still one of the most devastating films of the Century—and if you like Lonnergan’s You Can Count on Margaret, you’ll certainly like (if that’s even the word) this one too. Just be warned, this isn’t the easy-going what might have been? kind of weepy; this is a full-on, pull-your-heart-out tragedy, so make sure to steady yourself beforehand and maybe have a drink poured for after. 

That said, for this specific genre of film, it’s surprisingly rewatchable. The story takes place in the titular New England enclave and, somewhat like Hamnet, follows a woman (Michelle Williams) and a man (Casey Affleck) as they attempt to process the death of a child.

If you are a film-lover between the ages of 20-35, I can pretty much assume that Luca Guadagnino’s Call Me By Your Name has claimed at least a few drops from your lacrimal glands—and in case you’ve yet to see it, it’s an endlessly stylish and deeply felt queer coming-of-age film that fans of Carol and Moonlight will adore. 

The film stars Timothée Chalamet (in what was basically his breakout role) as a 17-year-old with an all-consuming crush on a slightly inappropriately older man. It takes place in Northern Italy in 1983, and yes, a peach is involved.

Of all the films on this list, I’d say I’ve probably watched Lady Bird the most times. Greta Gerwig’s debut (an instant classic that fans of Little Women will particularly love, not to mention a work that only grows in reputation as the years pass by), really has a bit of everything—humour, sincerity, great performances, nice tunes, relatable heartbreak and a genuinely deep well of sadness. 

Saoirse Ronan stars as the director’s eponymous stand-in, a charismatic and extroverted but refreshingly flawed teenager attempting to navigate the last year of high school—prom, boys, college, virginity, and a mother (a wonderful Laurie Metcalf) who loves her but—and here come the tears—might not actually like her all that much.

When you look back at it, A24 really had a monopoly on these kinds of movies for a while, there at the end of the 2010s. Bo Burnham’s beautiful debut Eighth Grade, a film I’ve watched at least four times, is a case in point—a movie that (like Lady Bird) never forgets to be funny, even when it's tearing your heart out.

Elsie Fisher stars as Kayla, a cool kid who hasn’t quite found her confidence yet. In her spare time, she offers musings to almost no one on her YouTube channel, but the film never mocks her for the effort and remains touchingly on her side throughout. The killer blow comes during a fireside chat, when we get to see her for a moment through her father’s loving eyes.

One of the biggest developments in how we watch movies in the last decade has been the rise and influence of meme culture. This has been something of a double-edged sword—some filmmakers seem to invite it with certain compositions (in the end of the day, free publicity is free publicity), but a particularly potent meme can sometimes overshadow a scene’s emotional power.

Case in point is Noah Baumbach’s relentlessly sad Marriage Story, which is now probably best known for the moment when Adam Driver punches a hole through the wall. If you can get past that familiarity, however, this is a movie on par with the director's early breakout, The Squid and the Whale and up there with the likes of Kramer vs Kramer in the pantheon of sad dad divorce stories. 

I feel guilty for only including one non-English language film on this list. Hirokazu Koreeda, in particular, has left me in bits on a few occasions over the last ten years, most notably with After the Storm, but Ryusuke Hamaguchi’s Drive My Car is the one that did the most damage. 

This is Hamaguchi’s follow-up to Wheel of Fortune and Fantasy, a movie I love even more, but when it comes to tears, you can’t do much better than this Oscar winner. The film follows a playwright as he works on a production of Uncle Vanya in the Japanese city of Hiroshima. Between rehearsals, while driving around town in the reddest Saab 900 you’ll ever see, he strikes up an unlikely and beautiful bond with his driver. If you’ve yet to see it, seek it out.

I was tempted to also add All of Us Strangers to this list, but given Paul Mescal’s presence in Hamnet (not to mention his devastating performance in Normal People), three mentions on one list just feels like overkill—even for an actor of his generational talent.

Whatever the case, Charlotte Welles’ exquisite semi-autobiographical debut feature, Aftersun (a film so famously heartbreaking that I’m pretty certain it influenced this year’s John Lewis advert), remains the actor’s finest moment—it was at least enough to secure him a shock nomination at the Academy Awards. He didn’t quite nick that, but he certainly took his fair share of tears.

We’ll end this list with a film that makes me cry just thinking about it—both for what it does and says, and also for the fact that it seems it will go down as Ken Loach’s final project. The Old Oak, like so many Loach films before, is a story about working-class solidarity—this time between TJ, a friendly publican in Durham, and Yara, a Syrian refugee. 

It’s an achingly beautiful piece of work, full of sadness and regret but not without a good dose of strength and hope to wash it down. And if you’ve ever enjoyed a Loach film (think movies like Kes, I, Daniel Blake or The Wind that Shakes the Barley), I highly recommend seeking it out. The director will hopefully celebrate his 90th birthday next year; let’s celebrate him while we can!