Oscar-winning movies come in many genres, but there’s always something special about the most romantic award-winning features. From the Golden Age of Hollywood until today, many romantic movies have become 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)
Oscar wins (1962) for West Side Story:
- Best Picture
- Best Director – Robert Wise and Jerome Robbins
- Best Supporting Actor – George Chakiris
- Best Supporting Actress – Rita Moreno
- Best Art Direction – Color
- Best Set Decoration
- Best Cinematography – Color
- Best Costume Design – Color
- Best Film Editing
- Best Scoring of a Musical Picture
- Best Sound
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 factions, 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 real 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)
Oscar wins (1997) for The English Patient:
- Best Picture
- Best Director – Anthony Minghella
- Best Supporting Actress – Juliette Binoche
- Best Art Direction
- Best Cinematography
- Best Costume Design
- Best Film Editing
- Best Original Dramatic Score
- Best Sound
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 at 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). The romance in The English Patient is steamy, passionate, and one anyone would dream of; as far as romantic movies go, this one is an all-time great.
8
‘La La Land’ (2016)
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Oscar wins (2017) for La La Land:
- Best Director – Damien Chazelle
- Best Actress – Emma Stone
- Best Cinematography
- Best Original Score
- Best Original Song – “City of Stars”
- Best Production Design
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 incorrectly. 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. Beyond love, the movie is also about self-discovery and ambition, but it’s hard to deny La La Land is one of the most romantic movies (and musicals) of all time.
7
‘Moulin Rouge!’ (2001)
Oscar wins (2002) for Moulin Rouge!:
- Best Art Direction
- Best Costume Design
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. Baz Luhrmann directed it as part of his Red Curtain trilogy, following Strictly Ballroom and Romeo + Juliet, and conceived it as a jukebox musical, combining various pop songs with original music.
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. As their forbidden love grows, the movie culminates in a tragic but grandiose finale, leaving viewers breathless. McGregor’s performance of “El Tango de Roxanne” is arguably the best moment in the movie, though Moulin Rouge! has more than enough of those to tug at the heartstrings.
6
‘Annie Hall’ (1977)
Oscar wins (1978) for Annie Hall:
- Best Picture
- Best Director – Woody Allen
- Best Actress in a Lead Role – Diane Keaton
- Best Original Screenplay – Woody Allen and Marshall Brickman
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. The movie covers themes of identity, sexuality, relationships, and their endings, but most of all, love, and how we can find it in every aspect of our lives.
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. Annie Hall isn’t just an awkwardly funny and beautifully realistic romantic movie; it has exceptional writing and a bold directing style, which Roger Ebert described as “a movie that establishes its tone by constantly switching between tones” and “a movie about a man who is always looking for the loopholes in perfection.”
5
‘Titanic’ (1997)
Oscar wins (1998) for Titanic:
- Best Picture
- Best Director – James Cameron
- Best Art Direction
- Best Cinematography
- Best Costume Design – Deborah Lynn Scott
- Best Film Editing
- Best Original Score – James Horner
- Best Original Song – “My Heart Will Go On”
- Best Sound
- Best Sound Editing
- Best Visual Effects
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. This romance doesn’t fall into the background even when the Titanic starts sinking; in fact, Jack and Rose’s love is the most enduring part of the movie.
4
‘Roman Holiday’ (1953)
Oscar wins (1954) for Roman Holiday:
- Best Actress in a Lead Role – Audrey Hepburn
- Best Story – Dalton Trumbo
- Best Costume Design, Black and White – Edith Head
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. While it wasn’t the first movie or romance set in Italy, this particular film sparked a great adoration for the country and its capital, making it possibly the most romantic setting any American love story could have.
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. It’s also interesting because they enjoy exploring that connection rather than jumping into a romance immediately, making Roman Holiday an unconventional romantic movie at that.
3
‘It Happened One Night’ (1934)
Oscar wins (1935) for It Happened One Night:
- Best Picture
- Best Actor in a Lead Role – Clark Gable
- Best Actress in a Lead Role – Claudette Colbert
- Best Adapted Screenplay – Robert Riskin
- Best Director – Frank Capra
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. Today, It Happened One Night is often lauded as one of the best meet-cutes in a romantic comedy, and generally put on lists of the best romantic comedies of all time. Colbert never expected to win Best Actress, but Clark Gable confidently delivered one of his best roles.
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)
Oscar wins (1940) for Gone With the Wind:
- Best Picture
- Best Actress in a Lead Role – Vivien Leigh
- Best Actress in a Supporting Role – Hattie McDaniel
- Best Director – Victor Fleming
- Best Screenplay – Sidney Howard
- Best Art Direction
- Best Cinematography, Color
- Best Editing
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.
Gone With the Wind is a historical epic romance, and follows Scarlett O’Hara (Leigh), the daughter of a rich plantation owner in Georgia. Scarlett pursues Ashley Wilkes (Leslie Howard), but as he’s about to be married, he pushes her away; because of that, Scarlett meets a new suitor, Rhett Butler (Gable). Scarlett and Rhett’s problematic and whirlwind romance suffers immense ups and downs, and the story doesn’t just follow their love, but the state of Scarlett’s home, and her family status after the Confederate loss. The lengthy Gone With the Wind is one of the biggest — in every sense of the word — romantic movies of all time.
1
‘Casablanca’ (1942)
Oscar wins (1944) for Casablanca:
- Best Picture
- Best Director – Michael Curtiz
- Best Adapted Screenplay
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 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 you, kid” celebrating the movie’s charm and love story.
Casablanca follows Rick Blaine (Bogart), who owns a gambling club in Casablanca, Morocco. Before coming to Casablanca, he was in Paris, where he met and fell in love with Ilsa Lund (Bergman); after she left without a warning or a goodbye, Rick became a hardened man and decided to leave everything behind. When Ilsa reappears in Casablanca, in Rick’s club, their whirlwind romance seemingly has some time left. Rick and Ilsa are probably the greatest on-screen couple, and Casablanca obviously shows that even after 83 years, romance never gets old.
Casablanca
- Release Date
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January 15, 1943
- Runtime
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102 minutes
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Humphrey Bogart
Rick Blaine
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