30. 500 Days of Summer
Have you ever wanted to love someone so much, and make something work so hard that you often overlooked signs that were there from the start? 500 Days of Summer captures young love and the unexpectedness of life in its full glory. Yes, 500 Days of Summer is not the happiest of stories, but it captures what a fizzled-out romance is all about. The honeymoon phase, the rough patch, the breakup, and then moving on. Everyone suffers heartbreak, but the love of friends and family can get you back up in the darkest of times. Remember there is always autumn waiting around the corner, so don’t get hung up on a summer fling. (Carl Broughton)
29. Spring
In the span of three films, Aaron Moorhead and Justin Benson have established themselves as two of the most exciting talents working in horror and fantastical cinema. Their second feature, Spring, is like Richard Linklater’s Before Sunset by way of H.P. Lovecraft. The story revolves around a grieving man who travels to Italy to escape the trouble he’s landed himself in back home. There, he meets a woman and falls head over heels for her. However, she’s harboring a secret that makes having a regular relationship quite awkward. To say more would spoil the movie, but just know that Spring is so much more than a horror movie with a romantic element. It’s a story of transcendental love that boasts genuine human warmth and pathos. It will make you laugh, cry, and root for a romance that deserves to succeed. The score by The Album Leaf’s Jimmy LaValle is also a masterpiece. (Kieran Fisher)
28. Punch-Drunk Love
In 1999, Paul Thomas Anderson wrote and directed Magnolia, a film whose mere existence (it is three hours long without a coherent narrative structure) is a testament to what a force the young auteur was considered to be at the time (and, let’s be honest, still is), after the breakout success of his 1997 film, Boogie Nights. That’s why many were shocked when Anderson started telling the press that his next project was going to be a romantic comedy starring Adam Sandler. While presumably, many laughed the prospect off, the final product was Punch-Drunk Love; a gorgeous, meticulously crafted, and wholly original love story, which is also, technically, an Adam Sandler comedy. The film tells the story of the socially awkward Barry Egan (Sandler), whose quiet existence is interrupted when he is introduced to Lena (the always lovely Emily Watson), and these two incredibly ordinary people fall magically in love. The best way to explain the power of this simple story is this line from an essay on the film by Miranda July for The Criterion Collection; “My favorite part of the movie is when Barry goes to Hawaii. He suddenly realizes he can just go to her, even without the frequent-flier miles. This is also my favorite thing in life: the sudden understanding that you aren’t condemned to sadness, that you can simply walk toward the thing you want.” If you’re looking for an outside-the-box romantic comedy, Paul Thomas Anderson has your back. (Madison Brek)
27. Brooklyn
Brooklyn features one of the cutest and purest courtships in movie history, but the film isn’t just about the adorable relationship between Eilis (Saoirse Ronan) and Tony (Emory Cohen). In many ways, Eilis falls in love with America in the same way she falls in love with Tony. It terrifies her at first and pulls her away from everything she’s ever known back in Ireland because she has always longed for that adventure. The beauty of the story is that it’s her love for Tony and the love she’s grown to have for her new country that compels her to leave her grieving mother and safe potential marriage with an Irishman played by Domhnall Gleeson. There are few men in romantic movies that are as patient, supportive, and just plain cute as Tony, and his love for Eilis is as romantic as it gets. (Emily Kubincanek)
26. The Shape of Water
Yes, a woman falling in love with a fish man is one of the most romantic movies out there. Not many movies portray love between two beings of different species who fall in love without any words. Taking notes from classic romance movies, Guillermo del Toro’s The Shape of Water sets a blooming crush to the dreamiest music, like Glenn Miller and Alice Faye. He puts this unconventional love up against some serious evil in the form of Michael Shannon, but it prevails as true love often does. The premise is seemingly unbelievable, but immediately we see the connection between Sally Hawkins’ Elisa and the Amphibian Man, and it defies all expectations for a romantic movie. If the poem in the end — “Unable to perceive the shape of You, I find You all around me. Your presence fills my eyes with Your love, It humbles my heart, For You are everywhere” –doesn’t make you bawl your eyes out, you might be heartless. (Emily Kubincanek)
25. Her
Spike Jonze has a knack for tackling unconventional stories, and that doesn’t change when it comes to the romance genre. A mustached Joaquin Phoenix plays our protagonist, a lonely man named Theodore left unhappy after his divorce from his childhood sweetheart. He finds solace when he purchases an operating system named Samantha (voiced by Scarlett Johansson), with whom he comes to grow a romantic bond through several conversations about the hardships of life and love. While the concept of dating an operating system might seem a little hard to get on board with at first glance, Jonze not only makes it convincing but renders it with such familiarity and empathy that it is near impossible to not become emotionally invested in Theodore’s romantic journey. Aided by the lush cinematography of a futuristic Los Angeles and a killer screenplay that won Jonze an Academy Award in 2014, Her reminds us that in the often alienating world we live in, all we’re really craving is a way to find that human connection with others. (Siobhan Spera)
24. The Umbrellas of Cherbourg
Jacques Demy knew how to pull at the ol’ heartstrings like no one else. Starring the incomparable Catherine Deneuve, The Umbrellas of Cherbourg sings and dances its way into your heart, takes root, and never lets go. Genevieve (Deneuve) and Guy (Nino Castelnuovo) are a young couple, madly in love, and convinced they’re meant to be together forever. The beautiful and rich color palette and the fact that all the dialogue in the film is sung allows Demy to envelop the viewer into Genevieve and Guy’s world — a world where everything is good and hopeful, a world where love never dies, a world full of promise. That is until reality comes calling and Guy is drafted into the Algerian war. The two are forced to negotiate their shared hope for their relationship and their place in the world, a process that is never easy and often heartbreaking. Umbrellas crescendos to a final scene that is as unforgettable as the film’s perfect soundtrack, which is courtesy of the late, legendary French composer Michel Legrand. (Anna Swanson)
23. 10 Things I Hate About You
Few films spark ’90s teen rom-com nostalgia more than 10 Things I Hate About You, a loose modernization of Shakespeare’s The Taming of the Shrew. But in lieu of the original play’s various psychological torments and subtle misogyny, we instead get prom, cute paintball dates, and Heath Ledger singing “Can’t Take My Eyes Off of You” on the football field bleachers. The film follows chronic pessimist Kat Stratford (Julia Stiles) as she attempts to breeze through her senior year without any unnecessary distractions — plans that are interrupted when the school’s “bad boy,” Patrick Verona (Ledger), comes into the picture after being solicited by a young Joseph Gordon-Levitt attempting to date Kat’s younger sister (Larisa Oleynik), whose strict father maintains that she can only date once Kat has a boyfriend of her own. While the film may follow the common rom-com archetype of enemies-turned-lovers, the chemistry between Stiles and Ledger and the film’s hilarious and relatable characters give it enough elevation to still resonate just as much with audiences today as it did in 1999. Shakespeare wishes he could write a romance this charming. (Siobhan Spera)
22. Moonstruck
Moonstruck is romantic the way grated parmesan is romantic. It’s simple, it’s cheesy, and there’s no such thing as “too much.” Here, romance comes in many forms. There’s the central fling between Ronny (Nicolas Cage) and Loretta (Cher); two spicy meatballs who thought they’d never fall in love again. There’s needy Cosmo (Vincent Gardenia) and self-assured Rose (Olympia Dukakis), returning to one another like binary stars. There are Rita (Julie Bovasso) and Raymond (Louis Guss), smitten with each other after all these years. The moon presides like a love god over the east river; radiating Vikki Carr ballads and La Bohème over every brownstone its light touches. There are curses, miracles, and melodrama; Nic Cage screaming decelerations of love and treachery for the cheap seats like a wounded romantic hero from one of his operas. Or, better yet, Cher sipping red wine alone in front of a roaring fire, surrounded by the spoils of her self-care. But, always, Moonstruck grounds its bombast in something more subtle and tender: the flush rosy glow of the Grand Ticino’s table lamps, the way Cosmo watches Loretta drop cubes of sugar into fizzing champagne, the gentle comedy of “I love him awful.” Luckily, here the love runs as deep as the mess, hurt, and exasperation. Things fall apart, but the moon (and its big romance) have a way of pulling them back together. (Meg Shields)
21. The Princess Bride
“Is this a kissing book?” Why yes, yes it is, and arguably one of the very best book-to-film adaptations of all time. Adapted for the screen by the legendary William Goldman (who also wrote the novel), Rob Reiner’s take on star-crossed lovers Westley (Carey Elwes at his most dashing) and Buttercup (Robin Wright, always amazing) is pure celluloid joy. It’s the sort of film with something for everyone. It’s got true love and sword fights and, of course, rodents of unusual size. Castles are stormed, fathers are avenged, and it all ends with our hero and heroine riding off into the sunset and sharing a swoon-worthy kiss. What more could you want? (Ciara Wardlow)
