Oscar-winning movies come in many genres, but there's always something special about the most romantic awarded features. From the Golden Age of Hollywood until today, many romantic movies became a staple of cinema, whether they were Oscar winners or nominees. The genre is a beautiful addition to the world of film in general, since it awakens something primal and simple within every human. Love is the essential feeling, the main motivator, and the reason for living.
While romance may not always take home the top awards, it definitely has a place in the world of the Oscars and the Academy's recognition. To the fans of the best Oscar-winning romantic movies, these are the best and most worthy winners, no matter what the public or the Academy's voters think about romance as a genre. The romantic movies that were "lucky" enough to be Oscar winners are brilliant pictures that deserved all their accolades.
10. 'West Side Story' (1961)
West Side Story is the kind of musical people remember for a long time after watching it. While musicals aren't everyone's cup of tea, the acting, singing, writing, and direction make West Side Story a special viewing experience. It showcases the conflict between two fractions, while two people from those sides are in love - it's Romeo and Juliet, but it's also about tensions between white and Puerto Rican residents in the Upper West Side, NYC. Natalie Wood and Richard Beymer portray the star-crossed lovers, though the realest star of the movie is Rita Moreno, who also won an Oscar for her portrayal of Anita.
Tony (Beymer), a member of the Jets group from the Upper West Side, attends a local dance with his best friend Riff (Russ Tamblyn). There, he meets Maria (Wood), who arrives with her best friend Anita (Moreno) and Anita's boyfriend and Maria's older brother, Bernardo (George Chakiris). Bernardo is the leader of the Sharks, an enemy group to the Jets, so, of course, Tony and Maria's romance is impossible. West Side Story is a beautifully made romantic tragedy that would make even the toughest individuals wag their fingers to some of its original songs, such as "I Feel Pretty," "Maria," or "America."
9. 'The English Patient' (1996)
The English Patient is one of those soapy romances people secretly love, though there's not much secret about the movie's incredible popularity when it was first released. It was Miramax's highest-grossing feature film at the time, and a clear Oscar favorite, though many considered it Oscar bait rather than a genuine contending film. Wherever fans are on that scale - basically, like it or not - The English Patient is undeniably romantic. It was adapted from Michael Ondaatje's book of the same name, which was in turn inspired by Hungarian pilot László Almásy, who had an interesting life during WWII.
In the movie, the eponymous English patient is portrayed by Ralph Fiennes; his face is largely covered in bandages, since he was found in an airplane crash site in the desert. The man's identity is unknown, and while his French nurse, Hanna (Juliette Binoche), cares for him, the story of László Almásy is slowly unraveled. He met and fell in love with Katharine Clifton (Kristin Scott Thomas) on one of his expeditions, and the two had to hide from Katharine's husband, George. In parallel, Hanna develops feelings for a British Sikh Lieutenant, Kip (Naveen Andrews).
8. 'La La Land' (2016)
When La La Land was mistakenly called out as Best Picture winner at the 2017 Oscars, there was shock and confusion as the card turned out to be read wrong. In some ways, the real winner, Moonlight, and La La Land, are permanently labeled by such a mistake. However, they're both movies that were, in many ways, the first of their time. Moonlight was the first LGBTQ+ winner, including an all-black cast; La La Land was Damien Chazelle's first musical, though his affinity for the genre was always present in his life.
The movie is often considered iconic for its use of color, clever costume design, and, of course, brilliant soundtrack. La La Land follows aspiring actress Mia (Emma Stone), who was inspired by her aunt to become an actress. During a traffic jam in LA, she rages out against Seb (Ryan Gosling), an aspiring musician and jazz club owner. As the two meet again, their love's progression is depicted through the original songs.
7. 'Moulin Rouge!' (2001)
Baz Luhrmann's Moulin Rouge! could have easily passed under the radar as an Oscar winner, but it counts. Though nominated for eight awards, it was kind of snubbed, let's face it. However, its campiness and over-the-top production, including the fact that Moulin Rouge! is a musical, may not be everyone's cup of tea. To those who love it, Moulin Rouge! is, without a doubt, one of the most romantic movies of all time.
Moulin Rouge! follows English writer Christian (Ewan McGregor) moving to Paris and meeting Henri de Toulouse-Lautrec (John Leguizamo); together, they write a musical called Spectacular Spectacular, and take the story to Moulin Rouge, trying to impress the main courtesan, Satine (Nicole Kidman). Christian and Satine fall madly in love, but Satine isn't only sick from tuberculosis, but is promised to another man.
6. 'Annie Hall' (1977)
The universally loved Woody Allen picture, Annie Hall is a romantic comedy about relationships; the movie was written specifically for Diane Keaton as the titular character, and she won a Best Actress Oscar for her charmingly strong performance. Allen wrote and directed the movie, and he stars alongside Keaton as the male lead.
Annie Hall follows Alvy (Allen), a shy and clumsy man who's had bad luck in love and has two marriages behind him. When he meets Annie (Keaton), the story follows the progression of their relationship, from all its ups and downs to the pivotal moments that cause tension and breakups. With Alvy looking back on his relationship with Annie, he tries to figure out what caused it to end.
5. 'Titanic' (1997)
Titanic is one of the most nominated movies of all time, and James Cameron wrote it after developing a fascination with shipwrecks. He was inspired by the heartbreaking true story of the Titanic, intertwining it with a tragic romance between two lovable and charming leads. It's pretty much a soapy romance between a rich girl and a poor boy, but the clichés and the soapiness aren't something that could take away from Titanic. The romance is tasteful and beautiful, making the tragedy of the Titanic a lot more impactful.
Titanic follows Rose (Kate Winslet), a member of an aristocratic English family, boarding the Titanic in 1912 with her fiancé Cal (Billy Zane) and mother Ruth (Frances Fisher). At the same time, Jack (Leonardo DiCaprio), a poor artist, boards the ship. The two meet on the ship's stern, and begin bonding; soon, they fall in love, despite Ruth and Cal's disapproval.
4. 'Roman Holiday' (1953)
Roman Holiday is the quintessential Audrey Hepburn movie; with her effortless style, grace, and elegance, Hepburn swept fans off their feet in every motion picture. None, however, made her as popular as her American debut in Roman Holiday, where she portrayed a princess running from her entourage while in Rome. The movie was a commercial and critical success, giving Hepburn a stellar beginning to her Hollywood career with a Best Actress Oscar.
Hepburn plays Princess Ann, who is on a European tour with her royal entourage. Tired of the events she's attended so far, Anne slips away from the embassy; while exploring Rome, she meets American journalist Joe Bradley (Gregory Peck). The two visit some of Rome's most famous spots, from the Trevi Fountain to the Colosseum, and a connection develops between them.
3. 'It Happened One Night' (1934)
It Happened One Night is a definite classic, but no one thought it'd be so warmly welcomed at the Academy Awards. It's fairly underrated, which has been the case from its inception; lead actress Claudette Colbert thought it was "the worst movie in the world" and Columbia Pictures had such low expectations that they didn't invest much in the movie's advertising.
It Happened One Night follows Ellie (Colbert), a spoiled heiress who runs away; while she's on the run, journalist Peter Warne (Gable) trails her on a bus, but the two end up stranded at a stop. This is kind of an enemies-to-lovers story, a trope that's one of the most popular in romantic movies, but Gable and Colbert have incredible chemistry together. In many ways, their dynamic, the writing, and the story are the ingredients of the original, prototype of the modern rom-com.
*2. 'Gone With the Wind' (1939)
Margaret Mitchell's 1936 novel Gone With the Wind is better known as the 1939 movie of the same name, starring Clark Gable and Vivien Leigh. Anyone who's ever been a film fan knows the names of Scarlett O'Hara and Rhett Butler, the iconic leads in a whirlwind romance set in the American South, in a plantation-owned family's wealthy home. With lots of controversy surrounding Gone With the Wind today, the title of being "most romantic" would make some critics disagree; historically, it's hard to deny this movie's impact on cinema, and romantic movies in general.
1. 'Casablanca' (1942)
Casablanca is undoubtedly the most legendary romantic movie, and one of the all-time favorites. With leads that have as much chemistry between them as a lab experiment, Casablanca shows off a movie romance that's is both memorable after the first watch and worth revisiting every so often. Humphrey Bogart and Ingrid Bergman star in one of the greatest movies in Hollywood history; there's rarely been a movie as quoted as Casablanca, with lines like "Frankly, my dear, I don't give a damn" and "Here's looking at kids" celebrating the movie's charm and love story.