29 Depressing Romantic Films That Will Always Make You Cry

You know those depressing, sappy movies that make you cry every time? The ones that left you completely certain that you understood what love's most devastating depths felt like at the age of 12, having never been on a single date? And the heartbreaking movies that still leave me in such pain even after perhaps having tasted love and loss myself?

Indeed, those. Honestly, we can't get enough of the tragic, romantic movies that make you cry. We fully understand that the majority of the characters are imaginary in the back of our thoughts (or, at the very least, are fictionalised adaptations of real people). However, the feelings and heartbreaks, successes and failures of love still feel completely genuine. Isn't that what really matters? We believed it.

We've compiled a list of the 29 most heartfelt films that are certain to bring you to tears every time since love's highs and all of its beyond-anguishing lows are handled in so many various ways in modern films. Even those of you who claim to lack tear ducts are welcome to participate!

Prepare to enjoy a sad love story (or several) and pass the Kleenex while you're at it.

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From the moment Ally (Lady Gaga) and Jackson (Bradley Cooper) cross paths at a gay nightclub when she is singing Edith Piaf's "La Vie En Rose," we were cheering for them. A star is born with Jackson's assistance, but so is an epic romance. Even when things start to turn, we're left believing (against all hope) that everything would work out for the best. It starts off with so much promise.

Have you already watched the Gaga and Cooper remake and cried? The 1937 version, starring Janet Gaynor and Fredric March, the 1954 version, featuring Judy Garland and James Mason, and the 1976 remake, starring Barbra Streisand and Kris Kristofferson, are all worthwhile watching. In conclusion, there have been many stars born!

Where to watch: Amazon.
Love, Simon (2018)
In the course of the movie, Simon looks for the elusive "Blue," and if Nick Robinson's portrayal of Simon doesn't make you smile at all of his potential loves, you are surely a monster. The scene where Simon's mother (played by Jennifer Garner) sits down and confronts Simon about being gay is the one that will have you crying (and inhaling along with you).

Where to watch: Amazon and Disney+
Romeo + Juliet (1996)

This is somewhat of a no-brainer considering the Shakespeare play is one of the saddest love stories of all time. But in our opinion, Baz Luhrmann's exquisite handling of the movie is what actually wins. You'll recite every speech in iambic pentameter, just like you learned in English class, thanks to the beach backdrop, the costume party, and, yep, Leonardo DiCaprio from the '90s.

Where to watch: Amazon.
Moonlight (2016)
The movie Moonlight will wrench, not just pull, your heartstrings. It depicts the tale of one young, gay Black man's journey to adulthood and was written and directed by Barry Jenkins. We follow Chiron as he comes to grips with his identity — and with the nature of his affections toward a close buddy, Kevin — in three pivotal life chapters. Chiron grew up poor in Miami with a mother who battles substance abuse and addiction. It's a must-see because it won Best Picture and was the first all-Black film and the first LGBTQ film to do so.

Where to watch: Hulu.
Portrait of a Lady on Fire (2019)
A truly beautiful film. Marianne (Noémie Merlant), a painter, is hired to covertly create Hélose's (Adèle Haenel) engagement portrait in this period drama set in France around 1770. Hélose, who isn't quite thrilled with the prospect of this union, spends five idyllic days with Marianne experiencing love, female-driven mysticism, and beach filmscapes. After watching, you might feel moved to continue your sobbing by turning on Vivaldi and despondently turning to page 28 of any book. (Please rely on us.)

Where to watch: Hulu and Amazon.
La La Land (2016)
Woof, that montage at the end. Although the Hollywood fairytale conclusion we were looking for was not presented in this film, it did allow us to cry in a cathartic way (and plenty of Ryan Gosling).