Oscar-winning moviescome 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 picturesthat deserved all their accolades.
10’West Side Story' (1961)
Directed by Jerome Robbins and Robert Wise
Oscar wins (1962) forWest Side Story:
West Side Storyis 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 makeWest Side Storya special viewing experience. It showcases the conflict between two fractions, while two people from those sides are in love -it’sRomeo and Juliet, but it’s also about tensions between white and Puerto Rican residentsin the Upper West Side, NYC.Natalie WoodandRichard Beymerportray the star-crossed lovers, though the realest star of the movie isRita 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 Storyis a beautifully made romantic tragedy that wouldmake even the toughest individuals wag their fingersto some of its original songs, such as “I Feel Pretty,” “Maria,” or “America.”
9’The English Patient' (1996)
Directed by Anthony Minghella
Oscar wins (1997) forThe English Patient:
The English Patientis 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 Patientis undeniably romantic. It was adapted fromMichael 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 byRalph 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). The romance inThe English Patientis steamy, passionate, and one anyone would dream of; as far as romantic movies go, this one is an all-time great.
The English Patient
8’La La Land' (2016)
Directed by Damien Chazelle
Oscar wins (2017) forLa La Land:
WhenLa La Landwasmistakenly called out as Best Picture winnerat the 2017 Oscars, there was shock and confusion as the card turned out to be read wrong. In some ways, the real winner,Moonlight, andLa La Land, are permanently labeled by such a mistake. However,they’re both movies that were, in many ways, the first of their time.Moonlightwasthe first LGBTQ+ winner, including an all-black cast;La La LandwasDamien Chazelle’s first musical, though his affinity for the genre was always present in his life.
The movie is often considerediconic for its use of color, clever costume design, and, of course, brilliant soundtrack.La La Landfollows 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 denyLa La Landis one of the most romantic movies (and musicals) of all time.
7’Moulin Rouge!' (2001)
Directed by Baz Luhrmann
Oscar wins (2002) forMoulin Rouge!:
Baz Luhrmann’sMoulin 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, itscampiness and over-the-top production, including the fact thatMoulin 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. Luhrmann directed it as part of his Red Curtain trilogy, followingStrictly BallroomandRomeo + 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 calledSpectacular 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, thoughMoulin Rouge!has more than enough of those to tug at the heartstrings.
6’Annie Hall' (1977)
Directed by Woody Allen
Oscar wins (1978) forAnnie Hall:
The universally lovedWoody Allenpicture,Annie Hallis 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 Hallfollows 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 Hallisn’t just an awkwardly funny and beautifully realistic romantic movie; it has exceptional writing and a bold directing style, whichRoger Ebertdescribed as “a movie that establishes its tone by constantly switching between tones” and “a movie about a man who is alwayslooking for the loopholes in perfection.”
Annie Hall
5’Titanic' (1997)
Directed by James Cameron
Oscar wins (1998) forTitanic:
Titanicis one ofthe most nominated movies of all time, andJames Cameronwrote 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, butthe clichés and the soapinessaren’t something that could take away fromTitanic. The romance is tasteful and beautiful, making the tragedy of the Titanic a lot more impactful.
Titanicfollows 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)
Directed by William Wyler
Oscar wins (1954) forRoman Holiday:
Roman Holidayis the quintessentialAudrey Hepburnmovie; 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 inRoman 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, makingRoman Holidayanunconventional romantic movie at that.
Roman Holiday
3’It Happened One Night' (1934)
Directed by Frank Capra
Oscar wins (1935) forIt Happened One Night:
It Happened One Nightis 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 actressClaudette Colbertthought it was “the worst movie in the world” and Columbia Pictureshad such low expectations that they didn’t invest much in the movie’s advertising. Today,It Happened One Nightis often lauded as one ofthe best meet-cutes in a romantic comedy, and generally put on lists ofthe best romantic comedies of all time. Colbert never expected winning Best Actress, butClark Gableconfidently delivered one of his best roles.
It Happened One Nightfollows 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 anenemies-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.
It Happened One Night
2’Gone With the Wind' (1939)
Directed by Victor Fleming
Oscar wins (1940) forGone With the Wind:
Margaret Mitchell’s 1936 novelGone With the Windis better known as the 1939 movie of the same name, starringClark GableandVivien Leigh. Anyone who’s ever been a film fan knows the names ofScarlett O’Hara and Rhett Butler, the iconic leads in a whirlwind romanceset in the American South, in a plantation-owned family’s wealthy home. With lots ofcontroversy surroundingGone With the Windtoday, 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 Windis 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 Confederacy loss. ThelengthyGone With the Windis one of the biggest - in every sense of the word - romantic movies of all time.
Gone with the Wind
1’Casablanca' (1942)
Directed by Michael Curtiz
Oscar wins (1944) forCasablanca:
Casablancais 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,Casablancashows off a movie romance that’s is both memorable after the first watch andworth revisiting every so often.Humphrey BogartandIngrid Bergmanstar in one of the greatest movies in Hollywood history; there’s rarely been a movieas 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 manand 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, andCasablancaobviously shows that even after 83 years,romance never gets old.
