Film
(500) Days of Summer
A breakup replayed out of order, jumping between the 500 days of a relationship to hunt for the exact moment it curdled. Playful with structure, drenched in a killer soundtrack, funny right up until it isn't. Made for anyone who's ever run their own relationship back on a loop — though it quietly admits whose memory you're actually watching.
If you liked this
Eternal Sunshine of the Spotless Mind2004
Another breakup told backwards through memory, but pushed into full science fiction — a man literally erasing an ex from his brain, with Jim Carrey doing devastating work against type.
But Far stranger and sadder than 500 Days, with less comic relief and more existential dread.

Annie Hall1977
The original nonlinear breakup comedy — fourth-wall breaks, split screens, a narrator picking through a relationship's corpse for laughs and answers. This is where the whole genre learned its tricks.
But Some viewers can't separate the film from what's since been learned about Woody Allen.

High Fidelity2000
Another self-absorbed narrator counting down his failed relationships, mixtapes standing in for greeting cards, funny and cutting about how men mythologize the women they've lost.
But Rob is even less self-aware than Tom, and the film lets him off easier for it.

The wildcard
Something you would not have found on your own.
The Worst Person in the World2021
Same structural device — a life measured out in numbered chapters — but told from the 'Summer' figure's side, refusing to be anyone's dream girl or cautionary tale.
Chaptered and time-skipping just like Tom's day-count, but it hands the microphone to the woman — funny, messy, Norwegian, and the corrective Summer never got to give herself.
But Subtitled, deliberately meandering, and less concerned with tidy comic beats than resolution.

More like this (8)
Scott Pilgrim vs. the World2010
Takes the exact same trope — unknowable dream girl as prize to be understood — and literalizes it into video-game boss battles. Visually dazzling, deliriously fun, same DNA in a louder costume.
But Its manic energy and stylization can feel exhausting if you wanted something quieter.

La La Land2016
A gorgeous, bittersweet musical about two people who love each other but not enough to save each other, with the same structural courage to end on ambivalence rather than resolution.
But It's a musical, unapologetically, and the ending divides people who wanted a clean romance.

Blue Valentine2010
Cuts between a relationship's giddy beginning and its bitter end at the same time, the structural trick 500 Days plays with, but stripped of whimsy and played devastatingly straight.
But Much heavier and rawer — no jokes to soften the blow, just two people falling apart.

Marriage Story2019
A brutally fair, alternating-perspective portrait of a relationship ending, with career-best performances and the same interest in how two people remember the same years so differently.
But This is a divorce, not a fling — heavier, longer, with zero whimsy to lean on.

Celeste & Jesse Forever2012no page yet
Same comedic-melancholic register, same interest in how long it takes to actually let go of someone, with a script that understands post-breakup limbo better than most.
But Rougher around the edges than 500 Days, with less confident tonal control.
Normal People2020
Charts an on-off relationship across years with the same interest in the small moments that quietly wreck things, but slower, quieter, and devastatingly intimate.
But A multi-episode commitment with a deliberately slow, ache-heavy pace throughout.

The Apartment1960
The same lovelorn-schmuck engine, decades earlier — a man who thinks he understands a woman's worth before realizing his fantasy of her was never really about her.
Billy Wilder's masterpiece disguised as an office comedy — whip-smart, deeply funny, and quietly heartbroken underneath, the direct ancestor of every wisecracking-but-wounded rom-com since.
But Black-and-white, 1960 pacing and studio-era manners can feel slow next to a soundtrack-driven indie.

Anomalisa2015
Same self-absorbed male fantasy of a woman as the answer to his problems, pushed into surreal, adult territory where the delusion gets nowhere to hide.
A stop-motion puppet film that turns 'she'll fix everything wrong with me' into something stranger and sadder — Charlie Kaufman using animation for very grown-up heartbreak.
But Slow, deliberately uncomfortable, and includes a puppet sex scene that startles anyone expecting cute.

People
Cast

Zooey DeschanelSummer
Geoffrey ArendMcKenzie
Chloë Grace MoretzRachel
Clark GreggVance
Patricia BelcherMillie
Rachel BostonAlison
Minka KellyAutumn- Charles WalkerMillie's New Husband
Ian Reed KeslerDouche
Darryl Alan ReedBus Driver
Directing
- Marc WebbDirector
- Renetta G. AmadorScript Supervisor
Writing
- Michael H. WeberWriter
- Scott NeustadterWriter
Production
- Veronica BrooksAssociate Producer
- Eyde BelascoCasting
- Scott HymanCo-Producer
- Jessica TuchinskyProducer
- Mark WatersProducer
- Mason NovickProducer
- Steven J. WolfeProducer
- Jenny HinkeyUnit Production Manager
Recommended by
How I Met Your Mother, Amélie, Eternal Sunshine of the Spotless Mind, Her, Scott Pilgrim vs. the World, When Harry Met Sally..., La La Land, Annie Hall, High Fidelity, Beginners, The Worst Person in the World, Two for the Road, Chungking Express, The Break-Up