One-sided love stories are brutal. At some point in our lives, we’ve all gone through the terrible feeling of unrequited love. And let’s be honest, it hurts. It pains inconsolably to realize that the person you love the most doesn’t love you back. Movies like 500 Days of Summer (which has now become some kind of cult phenomenon) are a perfect example of that feeling laid out right in front of us. This film, in particular, helps you overcome the feeling of losing the person you imagined your life with. Although the movie came almost a decade ago, it still holds up, and almost every person relates to the character Tom Hansen played by Joseph Gordon-Levitt. With that, most also cannot stand the character Summer (played by Zooey Deschanel), though time has told us that she wasn’t all that bad for breaking poor Tom’s heart.
So, what really makes the film special? Firstly, 500 Days of Summer is relatable to the tee. The struggle of asking out and being able to spend the day with the person you have a crush on just hits home for many of us. Living and reliving the moments where you realize that she is the one for you and shares a similar vibe about things in life becomes your only reality.
You can easily sympathize with Tom’s character. And although as clear as she is with her intentions, Summer looks at Tom in a way that only melts his heart in a manner we may/would have experienced in our lives. So, it is quite natural to be attracted to someone who also kind of reciprocates the feeling you have for them. Director Marc Webb understands that and does his best to replicate all of it in 500 Days of Summer.
To add to that, the movie also has music that makes up for every emotion you feel while watching it. From Belle & Sebastian to the Smiths, the soundtrack leads you to the moments of entering/living in a relationship that you know will only bring out the best (or worst in you.)
So, if you dig romantic comedies with cheesy-sappy moments, then here are 10 movies with the same vibe as 500 Days of Summer.
1. Annie Hall (1977)
The characters in Annie Hall are fairly reasonable, and the film effortlessly goes beyond the usual romantic story formula. Set in New York, Alvy is trying to understand why his relationship didn’t work with Annie. Woody Allen and Dianne Keaton play Alvy and Annie in the film, offering you moments of their time together from the first meeting to the last goodbye.
Even though it is touted as a classic, we do not give Annie Hall enough credit for birthing the rom-com genre. Like 500 days of Summer, the film beams sophistication and spits philosophies with laughs aplenty. The in-depth understanding of the two individuals who are entirely aware and unaware of what works for them, and most importantly, feel like believable characters, makes Annie Hall stand out from other films of that era.
Related to 500 Days of Summer – Annie Hall [1977]: A Wisdom Tooth for all Ages
2. High Fidelity (2000)
Here is another excellent example of an indie film like 500 days of Summer. It is hard to not recommend High Fidelity as far as romantic comedies about ‘love that was meant to be, but never happened’ are concerned. Released in 2000, when a lot of rom-coms came to light, this film, in particular, became a guilty pleasure for many romantic nerds. Adapted from Nick Hornby’s book by the same name, the John Cusack starrer is considered to be one of his most successful films to date.
Recently dumped by his girlfriend (which we get to know from the horse’s mouth; as he breaks the fourth wall throughout the film), Rob Gordon goes down memory lane to tell us about the top five breakups of all time. He plays an audiophile record store owner who is unlucky when it comes to falling in love. The film also stars Jack Black and Todd Louiso playing the perfect partners in the crime; helping Cusack’s character determine the various reasons behind his consistent failure to find true love.
3. Eternal Sunshine of the Spotless Mind (2004)
During their meet-cute moment, Joel (Jim Carrey) and Clementine are irrecoverably attracted to each other. Joel is a warm, introverted person, whereas Clementine (played by Kate Winslet) is free-spirited and jovial. Their conflicting personalities eventually lead to a bad breakup. When Joel gets to know his girlfriend underwent a procedure to erase him from her memory, he decides to do the same. Only to realize midway in the process – he wants to keep her memories because he still loves her. As his memory starts to fade away, he goes through all the tormenting and unforgettable experiences of being in love with Clementine.
Written by the legendary Charlie Kaufman and directed by Michel Gondry, the film instantly developed a cult following. Shaped purely based on the relationship between two individuals who have conflicting emotions of love and suffering, the movie’s creators downplayed the aspects of science-fiction to investigate the core of its psychological drama, making it a must-watch movie that also serves as a perfect double-bill with 500 days of summer.
Related to 500 Days of Summer – Of Love, Grief and Rediscovery: A Love Letter to Clementine
4. Two Lovers (2008)
Now here is an underrated recommendation to add to your watchlist if you were intrigued by 500 Days of Summer. Two Lovers, directed by James Gray explores a similar theme. In the film, Joaquin Phoenix plays a freelance photographer who moves back to his parent’s house after a breakup. He tries to battle his heartbreak and depression while figuring out his life and helping his parents with the dry-cleaning business. Leonard’s mother (Isabella Rossellini) arranges a meet-up with her (potential) business partner’s daughter Sandra (Vinessa Shaw), in the hope that her son will find love all over again.
On the other hand, Leonard accidentally meets Michelle (Gwyneth Paltrow.) He falls for her blond, sophisticated, intriguing personality. And starts to believe she likes him too. The film has an unusual approach to the whole idea of romance and traditional family melodrama. Those who love watching heartbreaking romantic movies with well-written, intense characters portraying the nuance of human emotions, should certainly give Two Lovers a shot.
5. Blue Valentine (2010)
Blue Valentine is considered to be one of the best romantic drama films of the last decade. Directed by Derek Cianfrance, the film explores the birth of a marital relationship as it slowly leads to a heartbreaking decay of two individuals who were once madly in love. After an irresistible meet-cute and accidental pregnancy, Dean and Cindy get married young in their life. Over time, every mundane morning, their life begins with frustrating and unresolved confrontations as they attend to the daily needs of their six-year-old daughter.
Extremely frustrated to see how their relationship is slowly collapsing, Dean suggests that Cindy join him for a one-night getaway to a honeymoon motel. He hopes this will help them get things back to life if they try to reconnect for old times’ sake. For people who want to cry while watching two misfits in a crumbling marriage; screaming in pain and agony – Blue Valentine is a must for you! While much darker and mature in tone when compared to 500 Days of Summer, the characters developed here are unbelievably real; showing their boredom, exhaustion, frustration, bitterness, and confusion at not being able to be in love, even when it felt like the most perfect things in the world.
Related to 500 Days of Summer – 6 Films to watch if you like The Gray Man on Netflix
6. Submarine (2010)
Submarine offers dark humor and self-aware ramblings about life, love, and fate; seen through the eyes of a 15-year-old Oliver Tate. Adapted from the coming-of-age novel with the same name, the film is the directorial debut of Richard Ayoade (you would know him from pop-culture memes catering to the IT Crowd).
Interestingly, the film begins with an introductory note that Submarine is an important film, and one must watch it with immense respect. Oliver has a lot of things he wants to achieve in his life. To begin with, losing his virginity before his 16th birthday tops the list. The second is to woo his moody ladylove Jordana and then fix the marital issues that his parents are currently going through.
From mentioning The Catcher in the Rye, a drawing of a young Woody Allen hung on the bedroom wall, to picking The Passion of Joan of Arc as a perfect date movie, this indie film uses Ayoade’s straight-faced comic observations to look at the futile nature of first love. Alex Turner (frontman of the rock band – Arctic Monkeys) provided an original soundtrack that blends seamlessly with the definition of the film, catering to people that go through heartbreak and understand the need to grow up at the same time.
7. Ruby Sparks (2012)
Ruby Sparks is essentially a rom-com with fantasy elements sprinkled all over. Directed by Little Miss Sunshine co-creators Johnathon Dayton and Valerie Faris, the film stars Paul Dano and Zoe Kazan (who wrote the film). It follows the life of Calvin – a young novelist wrapped in loneliness and isolation because of his inability to recreate his first book’s success.
His therapist suggests that he should write a few pages about someone who might like his dog. Although, soon, he happens to meet a strange woman in his dream; inspiring him to write again. However, the following night he finds the woman from his dream materializing and using his typewriter.
Slowly, as the story unfolds, he soon finds out that he is in love with the lead character (the woman) of this story that he is writing. Like Tom in 500 Days of Summer, the protagonist in Ruby Spark would daydream about his expectation for a better half, except actually going the extra mile to find it. Calvin is a lot like Tom because he cannot face his reality and is too eager to accept and live his fantasy pertaining to it as his actual reality.
Related to 500 Days of Summer – RUBY SPARKS [2012]: THE DECONSTRUCTION OF THE MANIC PIXIE DREAM GIRL PERSONA
8. What If (2013)
“I just want to be friends.” It is probably the only frightening sentence in a movie that one can hear as a possible red flag, after, of course, “I will find you, and I will kill you.” What If, circles around two charming individuals who meet at a party. Medical school dropout Wallace (the wizard boy, Danielle Radcliff) is still trying to overcome his heartbreak. Chantry is an animation artist who charms Wallace with her uber cuteness. Both of them are completely smitten with each other. Just like the characters in 500 days of Summer, these two also share likable interests and engage in conversation about different aspects of one’s life.
But here is the heartbreaker – Chantry has been happily involved with a long-distance boyfriend for five years. The film, adaptated from T.J.Dawe and Michael Rinaldi’s Toothpaste and Cigars, questions one of the most explored theories – whether people of the opposite gender be ‘just friends?
Remember When Harry Met Sally? Yes, pretty much that but with an even more complicated central conflict that definitely cannot have a happy ending. Like 500 Days of Summer, it is about confused people who don’t understand what they want when it comes to love. To add to that, there is also a cool sidekick in the form of Adam Driver.
If you are someone who loves effortless romantic conversations, discussing random life issues on long night strolls, and it’s easier for you to witness people battling their emotions of falling in love to avoid consequences, then What if is for you.
9. Comet (2014)
Sam Esmail’s Comet explores a kind of metaphysical, love-at-first-sight kind of romance that for some reason feels highly relatable. Justin Long who stars as Dell and Emmy Rossum who plays Kimberly are two different personalities. Dell is a highly philosophical, lost soul with a pessimistic mindset towards life, while Kimberly lives in the present, embracing life with all that it has in store for her.
The film offers a beautiful cinematic experience with its comet-striking theory of falling in love and trying to figure out how to make it work. It intercuts sequences from multiple dimensions to highlight the familiar moments of a newly forged relationship – including the meet-cute, break up, patch up and then break up again.
With a narrative that keeps you thoroughly engaged, Comet takes you through the phases of being in a relationship, with a constant sense of doubt about the future. Like 500 Days of Summer Dell feels like an extension of a person who lives more in his head than he does in the real-life scenario. Comet is a must-watch for people who dig heartfelt romantic movies with a sense of otherworldliness.
Related to 500 Days of Summer – 9 Films to Watch if you like Don’t Look Up on Netflix
10. Before We Go (2014)
The directorial debut of actor Chris Evans, Before We Go feels like a typical rom-com. Taking place over a span of a single night, the film follows a boy who meets a girl at Manhattan’s Grand Central Station around 1.30 am. It is cold outside and walking in the city engaged in long conversations about life and dreams, makes people who were strangers a few hours ago, fall in love.
The characters in the film are no different than usual romantic movies – a boy lost in love, uncertain about his life, and a girl going through a marital crisis stuck at crossroads. However, the on-screen chemistry of Chris Evans and Alice Eve (playing Nick and Brooke) is remarkable and makes you believe that their issues in life are as true-to-life as anyone else’s. Almost giving you a Before Sunrise vibe (brief encounter and falling in love with the right person at the wrong time), this one is worth the watch if you are someone who loves movies like 500 Days of Summer.
500 Days of Summer (2009) Movie Links – IMDb, Rotten Tomatoes
500 Days of Summer (2009) Movie Cast – Joseph Gordon-Levitt, Zooey Deschanel, Geoffrey Arend, Matthew Gray Gubler, Chloë Grace Moretz
