22 Oscar Winning Romantic Movies

From classics to unforgettable love stories, discover Oscar-winning movies that will make you swoon. Find your next romantic film here!

Oscar Winning Romantic Movies
Mehran Khan By Mehran Khan - Author 14 Min Read

Love stories have a special place in our hearts. We review Oscar-winning romantic movies, some in comedy and some in drama.

Forrest Gump (1994)
Forrest Gump (1994)

1. Forrest Gump (1994) – IMDB Rating 8.8

A man with a low IQ achieves great things in his life by doing much more than anyone else thought he could do. But despite everything he has achieved, his one true love eludes him. Winning the Oscars for Best Picture, Best Editing, and Best Visual Effects, “Forrest Gump” won Best Actor for Tom Hanks, Best Director for Robert Zemeckis, and Best Adapted Screenplay for Eric Roth.

Moonstruck (1987)
Moonstruck (1987)

2. Moonstruck (1987) – IMDB Rating 7.1

One of the most cult romantic comedies, “Moonstruck” by Norman Jewison, tells the difficult situation in which Loretta finds herself, as she falls in love with the brother of the man she agreed to marry. The cast of the movie “Moonstruck”, which won the Oscar for Best Actress, Best Supporting Actress, and Best Screenplay, includes names such as Cher, Nicolas Cage, Olympia Dukakis, and Danny Aiello.

The Sound of Music (1965)
The Sound of Music (1965)

3. The Sound of Music (1965) – IMDB Score 8.1

In the years before World War II, a woman becomes a governess in the home of a widowed sea captain with seven children and brings home a new love of life and music. The movie, starring Julie Andrews and Christopher Plummer, is directed by Robert Wise. “The Sound of Music” won Oscars for Best Picture, Best Director, Best Sound, Best Editing and Best Music.

Roman Holiday (1953)
Roman Holiday (1953)

4. Roman Holiday (1953) – IMDB Rating 8.0

A bored princess escapes her guards and falls in love with an American journalist in Rome. “Roman Holiday”, for which Audrey Hepburn won the Oscar for Best Actress, also won awards for Best Screenplay and Best Costume Design.

Crazy Heart (2009)
Crazy Heart (2009)

5. Crazy Heart (2009) – IMDB Score 7.2

A faded country musician is forced to re-evaluate his dysfunctional life and a relationship that inspires him but is not good for him. Directed by Scott Cooper and starring Jeff Bridges, Maggie Gyllenhaal, and Colin Farrell, “Crazy Heart” won the Oscars for Best Actor and Best Song.

The Shape of Water (2017)
The Shape of Water (2017)

6. The Shape of Water (2017) – IMDB Score 7.3

In a secret research facility in the 1960s, we follow the romance between a lonely cleaner and a mysterious creature who is being held captive because he is being researched. Guillermo del Toro is the director of “The Shape of Water”, which won the Oscar for Best Director, Best movie, Best Music, and Best Production Design, while the cast includes Sally Hawkins, Octavia Spencer, Michael Shannon, Doug Jones and Names like Richard Jenkins appear.

Titanic (1997)

7. Titanic (1997) – IMDB Score 7.9

The story of the incident in which many people lost their lives when the Titanic passenger ship, which was said to be unsinkable, crashed into an iceberg and sank, is told through the story of an aristocratic young girl falling in love with a poor artist who met on the ship. Written and directed by James Cameron, “Titanic” stars Leonardo Dicaprio and Kate Winslet. During the production of the movie, James Cameron went down to the wreck of the Titanic with a small submarine and researched to ensure that the ship in the movie was authentic. “Titanic” won the Oscars in 1998 for Best Movie, Best Director, Best Cinematography, Best Art Direction, Best Costume Design, Best Sound, Best Editing, Best Sound Editing, Best Visual Effects, and Best It became the most notable movie of the ceremony, winning Oscars in 11 categories, including Best Song and Best Music.

Casablanca (1942)
Casablanca (1942)

8. Casablanca (1942) – IMDB Score 8.5

Starring Humphrey Bogart and Ingrid Bergman, “Casablanca” is one of the most famous movies of all time. We watch as a cafe owner tries to decide whether or not to help her ex-boyfriend and her husband escape from the Nazis. “Casablanca”, for which Michael Curtiz won the Best Director award, also won the Oscars for Best Picture and Best Screenplay.

The Brokeback Mountain (2005)
The Brokeback Mountain (2005)

9. The Brokeback Mountain (2005) – IMDB Score 7.7

Ennis and Jack, a cowboy and a farmer in love, are stuck in the chaos of their relationship while marrying their girlfriends. “The Brokeback Mountain”, directed by Ang Lee and starring Jake Gyllenhaal, Heath Ledger, Michelle Williams, and Anne Hathaway, won the Oscars for Best Director, Best Adapted Screenplay, and Best Score.

The English Patient (1996)
The English Patient (1996)

10. The English Patient (1996) – IMDB Score 7.4

At the end of World War II, a young nurse tries to heal a badly burned plane crash victim. While we learn about the patient’s past, we also witness the fate of their love. “The English Patient” is an Oscar winner for Best Picture, Best Supporting Actress, Best Director, Best Cinematography, Best Art Design, Best Costume Design, Best Sound, Best Editing, and Best Music.

Out of Africa (1985)
Out of Africa (1985)

11. Out of Africa (1985) – IMDB Score 7.1

Adapted from the autobiography of Danish writer Karen Blixen, the movie is about Blixen moving to Africa at the beginning of the 20th century to start a new life for herself. “Out of Africa” ​​won the Oscars for Best Picture, Best Adapted Screenplay, Best Director, Best Cinematography, Best Art Direction, Best Music and Best Sound.

Annie Hall (1977)
Annie Hall (1977)

12. Annie Hall (1977) – IMDB Score 8.0

“Annie Hall”, which revolves around the relationship between divorced comedian Alvy Singer and his ex-girlfriend, musician Annie Hall, is one of the movies in which we see Woody Allen’s style most clearly. Best Picture winner “Annie Hall” won the Oscars for Best Director for Woody Allen, Best Actress for Diane Keaton, and Best Original Screenplay for Woody Allen and Marshall Brickman.

Gigi (1958)
Gigi (1958)

13. Gigi (1958) – IMDB Score 6.6

Tired of the traditions of Parisian high society, a wealthy playboy and young Gigi enjoy a platonic friendship that may not remain platonic for long. Directed by Vincente Minnelli, “Gigi” won nine awards in the categories of Best Picture, Best Director, Best Adapted Screenplay, Best Cinematography, Best Art Direction, Best Costume Design, Best Editing, Best Music and Best Song. Oscar Award winner.

The Apartment (1960)
The Apartment (1960)

14. The Apartment (1960) – IMDB Score 8.3

A Manhattan insurance clerk tries to get promoted at his company by letting his managers use his home for appointments. However, things get complicated and love arises for him. Best Picture winner “The Apartment”, which earned Billy Wilder the Oscars for Best Director and Best Screenplay, also won Oscars for Best Art Direction and Best Editing.

The Reader (2008)
The Reader (2008)

15. The Reader (2008) – IMDB Score 7.6

Nearly a decade after his relationship with a woman mysteriously ended, law student Michael Berg re-encounters his ex-lover defending himself in a war crimes trial in post-World War II Germany. The script of “The Reader”, for which Kate Winslet won the Oscar for Best Actress, was adapted by David Hare from Bernhard Schlink’s book “Der Vorlesser”.

West Side Story (1961)
West Side Story (1961)

16. West Side Story (1961) – IMDB Score 7.6

Adapted for the big screen from the Broadway musical of the same name, “West Side Story” brings a modern adaptation of the love of Shakespeare’s unforgettable heroes, Romeo and Juliet, to the streets of New York. “West Side Story” won the Oscars for Best Movie, Best Supporting Actress, Best Supporting Actor, Best Director, Best Cinematography, Best Art Direction, Best Costume Design, Best Sound, Best It won awards for Best Editing and Best Music.

My Fair Lady (1964)
My Fair Lady (1964)

17. My Fair Lady (1964) – IMDB Score 7.8

Starring Audrey Hepburn and Rex Harrison, “My Fair Lady” tells the story of snobby professor Henry Higgins in 1910s London, who bets that he can make Eliza Doolittle, a vulgar flower girl, glamorous to fit in with high society. “My Fair Lady” is an Oscar winner for Best Picture, Best Actor, Best Director, Best Cinematography, Best Art Direction, Best Costume Design, Best Sound and Best Music.

It Happened One Night (1934)
It Happened One Night (1934)

18. It Happened One Night (1934) – IMDB Score 8.1

An evil reporter and a crazy young heiress meet on a bus heading to New York and are obliged to each other when the bus drops them off at one of the stops. The movie “It Happened One Night”, starring Clark Gable and Claudette Colbert and directed by Frank Capra, won the Oscars for Best Picture, Best Actor, Best Actress, Best Director, and Best Adapted Screenplay.

Gone with the Wind (1939)
Gone with the Wind (1939)

19. Gone with the Wind (1939) – IMDB Score 8.2

The manipulative daughter of a Georgia landowner has a tumultuous romance with a rebellious profiteer during the American Civil War and Reconstruction eras. “Gone With The Wind” won Best Actress, Best Supporting Actress, Best Director, Best Screenplay, Best Cinematography, Best Art Direction, Best Editing, and Best Actress at the Oscars, where William Cameron Menzies was given the Honorary Award. It won an award for Best Movie.

Moulin Rouge (2001)
Moulin Rouge (2001)

20. Moulin Rouge (2001) – IMDB Score 7.6

Winner of the Oscars for Best Art Direction and Best Costume Design, “Moulin Rouge” tells the story of a poor Bohemian poet in 1890s Paris who falls in love with a beautiful nightclub star who is obsessed with a jealous duke. Directed by Baz Luhrmann, “Moulin Rouge” stars Nicole Kidman, Ewan McGregor, Richard Roxburgh, John Leguizamo and Jim Broadbent.

La La Land (2016)
La La Land (2016)

21. La La Land (2016) – IMDB Score 8.0

“La La Land”, a musical movie written and directed by Damien Chazelle, starring Emma Stone and Ryan Gosling, tells the story of a pianist and an actress in Los Angeles trying to maintain their love while trying to achieve their dreams for the future. “La La Land” is an Oscar winner for Best Actress, Best Director, Best Cinematography, Best Music, Best Song, and Best Production Design.

Eternal Sunshine of the Spotless Mind (2004)
Eternal Sunshine of the Spotless Mind (2004)

22. Eternal Sunshine of the Spotless Mind (2004) – IMDB Score 8.3

“Eternal Sunshine of the Spotless Mind” won the Oscar for Best Screenplay. It tells the story of a couple who want to forget their bad relationship and undergo an experimental procedure. However, when love knocks on their door again, their confusion returns along with their memories. The famous cast of the movie includes names such as Jim Carrey, Kate Winslet, Tom Wilkinson, Elijah Wood, Mark Ruffalo, and Kirsten Dunst.

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Mehran Khan is a Software Engineer, tech enthusiast who also has a great passion in writing. During his 10+ years of career, he has covered news, features, and evergreen content on multiple platforms. Apart from keeping a close eye on emerging tech developments, he likes wasting time at the gym.