10 best movies like ‘500 Days of Summer’

It’s hard for a romcom to toe the line between providing something fresh while also giving the audience the story beats they’ve grown to know and love. But when the indie film 500 Days of Summer was released in 2009, it executed a new twist on the genre while still making viewers feel that same feeling they get from classics like When Harry Met Sally — even with the fact the film’s two protagonists don’t end up together.

500 Days of Summer fast became a sleeper hit and was on tons of “best-of” lists for that year, and its critical and commercial success reminded audiences why its stars (Zooey Deschenel and Joseph Gordon-Levitt) were such hot properties. If you vibed with the film back in the day and want to watch something similar, or have only just seen it and are desperate for more content like it, then check out our list of the 10 best movies like 500 Days of Summer.

Crazy Stupid Love

A charming little flick with a stellar cast, Crazy Stupid Love is full of laughs and heart, and much like 500 Days of Summer shows romantic relationships at every stage, from their most gloriously intoxicating to the heartwrenchingly painful. Cal (Steve Carrrell) is shocked when his wife Emily (Julianne Moore) hands him divorce papers. He wallows in a bar, and begins loudly complaining about his life, only for Jacob (Ryan Gosling), a playboy, to overhear him and begin coaching him how to pick up women. Jacob reveals he’s just been rejected by a woman named Hannah (Emma Stone), and the two men soon form an unlikely friendship. Jacob eventually manages to enter a relationship with Hannah (in no small thanks to a tip from Dirty Dancing) only for the new couple to realize Hannah is Cal and Emily’s eldest child, leaving Cal upset at his daughter’s choice of partner. From there, everyone’s relationships are tested, leading to an earned and somewhat ambiguous ending, as we’re left wondering if Cal and Emily reconcile.

Only You

Part of the reason 500 Days of Summer felt so real was the believability of the initial attraction between the two leads, and this British romcom has that in spades. Only You charts the relationship of cynical about love Elena (Laia Costa) and hopeless romantic Jake (Josh O’Connor), two strangers who meet by chance and soon become totally infatuated with each other. The pair’s chemistry is undeniable, and as the thread that needles through their relationship tightens and frays thanks to their insecurities and issues, you’re always rooting for them. Unlike 500 Days of Summer this one is a better ending for the romantics, but it really gets to the heart of how much love can bear, and what can eventually sever a tie.

Annie Hall

Whatever you think about Woody Allen (and there’s a lot of not great things to think about him), there’s no denying Annie Hall is an all-time classic. Allen, like in almost all of his films, basically plays himself in this smart satire of a romcom, in which he chronicles his failed relationship with the titular character (Diane Keaton) and tries to figure out just how he managed to mess it all up. Like 500 Days of Summer, there’s a huge slice of self awareness in the movie, and both characters (despite their absurdity) are wholly believable. Nearly five decades on it still feels fresh and funny, despite the outdated references, and it’s definitely Allen’s most relatable work (and most would argue his best). Great for fans who want the sweetness without too much sacharine.

High Fidelity

This 2000s adaptation of Nick Hornby’s novel of the same name is a truly brilliant bit of film that, like 500 Days of Summer, revolves around the main character trying to figure out why his partner left him via recounting his most painful breakups to the audience. John Cusack stars as Rob, a record store owner and pop culture obsessive who loves listing his top-five favorite things of everything from records to chocolate bars. We see Rob grow slowly throughout the narrative, and by the end he seems to have become something like a real life adult, although his little quirks continue. Widely praised for its realism and relatable characters, the film is a great study in what makes love tick, and what can suffocate it.

Blue Valentine

Blue Valentine is another film that follows a failed relationship via a non-linear narrative, and like 500 Days of Summer a smart script is elevated by brilliant performances, this time from Ryan Gosling and Michelle Williams. However, unlike the film that inspired this list, it covers a period of multiple years, from the beginnings of their relationship right until their marriage explodes in a fiery argument. The movie was number one of a huge amount of critical top-ten lists for the year (2010) and earned Williams an Oscar nomination. An engrossing watch, even as we see love falter, stall, and eventually die.

Punch Drunk Love

For all the jokes made about his seemingly superhuman ability to get millions of dollars to make mediocre films, when Adam Sandler shines he really sparkles (see also: Uncut Gems, Big Daddy, Happy Gilmore, etc.), and he’s excellent in this raw but sweet romcom. He stars as Barry, an unbearably anxious and slightly unstable salesman who falls in love with one of his sister’s co-workers (Emily Watson). A bit of a weird film marked by quirky yet intense characters, this touching portrait of a strange man who just wants to be loved really is as gripping as it is sweet, and like 500 Days of Summer really delves into what love is, and how we have to make it work ourselves. A fun, intriguing watch with a mostly happy ending, this is a great film for when you want to feel that love really can conquer all.

Silver Linings Playbook

With themes of finding yourself, and a similar blend of sad and sweet, Silver Linings Playbook is an ideal watch for people who loved 500 Days of Summer. It stars Bradley Cooper as Pat, a bipolar man who’s just been released from a psych ward and has to move back into his parents’ home (Robert De Niro and Jacki Weaver). Pat makes winning back his estranged wife (Brea Bee) his sole aim, but instead, he ends up connecting with a young widow (Jennifer Lawrence), who tells him she’ll help him to win his wife back if he enters a dancing competition with her. As they get closer, the pair re-examine how they relate to each other, and eventually realize they have feelings for each other. Silver Linings Playbook was nominated for eight Oscars, and when you watch it’s easy to see why.

Juno

Not quite a love story that doesn’t work out, but a story about making hard choices about things you might love, Juno gave Elliot Page their breakout role. Their standout performance as a pregnant teen helped to give the film that same quirky charm blended with devastating emotional scenes that makes 500 Days of Summer such an engrossing watch. Michael Cera is brilliant alongside Page, adding to the offbeat humor in the way that he makes seems so natural (or unnatural, such is his supreme ability to display awkwardness on screen). Cute, a little sad, but mostly sweet, a movie well worth spending an afternoon watching.

Eternal Sunshine of the Spotless Mind

Whereas 500 Days of Summer is about a relationship that seems perfect but ends in nothing, this romantic sci-fi film delves more into how we are sometimes drawn to certain people, whether we like it or not. Jim Carey plays Joel, a man who runs into his ex Clementine (Kate Winslet) and discovers she’s had a new procedure that allows people to have memories with certain people removed from their consciousness. Hurt, Joel tries to get the same procedure, only for him to realize he isn’t ready to give up on love just yet. Both leads were magnetic in this brilliant film, which earned a lot of deserved praise from critics and audiences alike.