22 Oscar-Winning Romantic Movies

Romantic movies have a special way of touching our hearts. Whether they make us laugh, cry, or dream, the best romantic films leave a lasting impact. And when a romantic movie wins an Oscar, it signals that it has truly resonated with both audiences and critics alike. In this article, we take you through a curated list of 22 Oscar-winning romantic movies that have made history. From timeless classics to contemporary hits, these films have captured the magic of love on screen and claimed the highest accolade in cinema.

Oscar-Winning Romantic Movies

1. Titanic (1997)

No list of Oscar-winning romantic movies is complete without “Titanic”. Directed by James Cameron, this epic love story swept the 70th Academy Awards by winning 11 Oscars, including Best Picture and Best Director. The movie follows the passionate romance between Jack (Leonardo DiCaprio) and Rose (Kate Winslet), two young people from different social classes who meet aboard the ill-fated RMS Titanic.

The story is as much a grand romance as it is a tragic tale of loss, with the romance between the lead characters being the beating heart of the film. “Titanic” became a cultural phenomenon and continues to be remembered as one of the greatest Oscar-winning romantic movies ever made.

Why It’s an Iconic Oscar Winner:

• Awards: 11 Oscars, including Best Picture, Best Director, and Best Original Song (“My Heart Will Go On”).
• Romantic Highlights: The iconic “I’m flying” scene and Jack’s famous line, “You jump, I jump.”

2. Gone with the Wind (1939)

Another legendary title in the list of Oscar-winning romantic movies is “Gone with the Wind”. This 1939 classic, directed by Victor Fleming, is based on Margaret Mitchell’s novel and tells the story of Scarlett O’Hara (Vivien Leigh), a Southern belle, and her complex romantic relationships during the American Civil War and Reconstruction era.

Winning 10 Academy Awards, including Best Picture, Best Actress for Vivien Leigh, and Best Director, “Gone with the Wind” remains an epic portrayal of love and passion against the backdrop of war and hardship.

Why It’s an Iconic Oscar Winner:

• Awards: 10 Oscars, including Best Picture, Best Director, and Best Actress for Vivien Leigh.
• Romantic Highlights: The stormy and unforgettable relationship between Scarlett and Rhett Butler (Clark Gable), and the famous line, “Frankly, my dear, I don’t give a damn.”

3. La La Land (2016)

“La La Land” is a modern-day musical romance that took the world by storm and secured 6 Oscars at the 89th Academy Awards, including Best Director for Damien Chazelle and Best Actress for Emma Stone. The film beautifully tells the story of two dreamers—Mia (Emma Stone), an aspiring actress, and Sebastian (Ryan Gosling), a passionate jazz musician—who fall in love while chasing their respective dreams in Los Angeles.

Though their love story is bittersweet and doesn’t follow the conventional happy-ever-after trope, “La La Land” still captures the essence of romantic passion and ambition, making it a beloved entry among Oscar-winning romantic movies.

Why It’s an Iconic Oscar Winner:

• Awards: 6 Oscars, including Best Director and Best Actress for Emma Stone.
• Romantic Highlights: The dreamy “A Lovely Night” dance sequence and the heart-wrenching “City of Stars” song.

4. Shakespeare in Love (1998)

Winning 7 Oscars, including Best Picture and Best Actress for Gwyneth Paltrow, “Shakespeare in Love” is a romantic period drama that imagines a love affair between William Shakespeare (Joseph Fiennes) and Viola de Lesseps (Gwyneth Paltrow). Set in the late 16th century, the film mixes historical and fictional elements as Shakespeare finds inspiration for his iconic play “Romeo and Juliet” through his romance with Viola.

The witty dialogue, humorous moments, and passionate love story helped make this film a favorite among both critics and audiences, securing its place as one of the most cherished Oscar-winning romantic movies.

Why It’s an Iconic Oscar Winner:

• Awards: 7 Oscars, including Best Picture and Best Actress.
• Romantic Highlights: The blossoming love between Shakespeare and Viola, culminates in one of the most memorable kisses in film history.

5. Casablanca (1942)

When talking about timeless Oscar-winning romantic movies, “Casablanca” is often the first to come to mind. Directed by Michael Curtiz, this 1942 classic is set during World War II and tells the story of Rick Blaine (Humphrey Bogart), a cynical nightclub owner in Casablanca, and his former lover Ilsa Lund (Ingrid Bergman), who unexpectedly walks back into his life.

“Casablanca” won 3 Oscars, including Best Picture, and remains an all-time favorite for its touching romance, memorable quotes (“Here’s looking at you, kid”), and emotional depth. It’s a must-watch for anyone who appreciates classic cinema and romantic storytelling.

Why It’s an Iconic Oscar Winner:

• Awards: 3 Oscars, including Best Picture.
• Romantic Highlights: The heart-wrenching scene where Rick and Ilsa must say goodbye at the airport, with Rick sacrificing his love for Ilsa’s happiness.

6. The English Patient (1996)

“The English Patient”, directed by Anthony Minghella, is another sweeping romance that earned multiple accolades at the 69th Academy Awards. The film won 9 Oscars, including Best Picture, Best Director, and Best Supporting Actress for Juliette Binoche. This epic love story follows a burn victim (Ralph Fiennes) who is cared for by a nurse (Juliette Binoche) as he recalls a passionate affair with a married woman (Kristin Scott Thomas) during World War II.

With its lush cinematography, gripping narrative, and tragic love story, “The English Patient” is an unforgettable film and one of the most moving Oscar-winning romantic movies of the 1990s.

Why It’s an Iconic Oscar Winner:

• Awards: 9 Oscars, including Best Picture and Best Supporting Actress.
• Romantic Highlights: The tender moments between Fiennes and Scott Thomas’ characters, set against the backdrop of the Sahara Desert.

7. Annie Hall (1977)

Unlike many of the sweeping epics on this list, “Annie Hall” is a romantic comedy that won 4 Oscars, including Best Picture, Best Director for Woody Allen, and Best Actress for Diane Keaton. The film is a witty, often humorous take on the complexities of relationships and love, with Allen playing Alvy Singer, a neurotic New Yorker who falls for the quirky Annie Hall (Diane Keaton).

With its sharp dialogue and clever storytelling, “Annie Hall” remains one of the best Oscar-winning romantic movies that explores the ups and downs of modern romance.

Why It’s an Iconic Oscar Winner:

• Awards: 4 Oscars, including Best Picture and Best Actress.
• Romantic Highlights: The charming relationship between Alvy and Annie, and the realistic portrayal of their love, complete with its imperfections.

8. The Shape of Water (2017)

“The Shape of Water”, directed by Guillermo del Toro, won 4 Oscars, including Best Picture, Best Director, and Best Original Score at the 90th Academy Awards. This unconventional love story between Elisa (Sally Hawkins), a mute woman, and a mysterious aquatic creature kept in a government facility, is a moving and imaginative exploration of love beyond societal norms.

With its lush visuals and compelling performances, “The Shape of Water” became a standout in recent years and earned its place as a modern entry among Oscar-winning romantic movies.

Why It’s an Iconic Oscar Winner:

• Awards: 4 Oscars, including Best Picture and Best Director.
• Romantic Highlights: The intimate connection between Elisa and the creature, culminates in a visually stunning underwater scene.

9. Out of Africa (1985)

Based on the autobiographical writings of Karen Blixen, “Out of Africa” won 7 Oscars, including Best Picture and Best Director for Sydney Pollack. The film tells the story of Karen (Meryl Streep), a Danish baroness, and her romantic affair with a big-game hunter named Denys (Robert Redford) in Kenya during the early 20th century.

With sweeping landscapes and a deeply emotional love story, “Out of Africa” remains a classic among Oscar-winning romantic movies that blends romance, adventure, and history.

Why It’s an Iconic Oscar Winner:

• Awards: 7 Oscars, including Best Picture and Best Director.
• Romantic Highlights: The passionate love affair between Karen and Denys, set against the breathtaking beauty of Africa.

10. My Fair Lady (1964)

“My Fair Lady” is a musical adaptation of George Bernard Shaw’s play “Pygmalion”, which tells the story of a poor flower girl, Eliza Doolittle (Audrey Hepburn), who is transformed into a refined lady by Professor Henry Higgins (Rex Harrison). Directed by George Cukor, this beloved musical won 8 Oscars, including Best Picture and Best Actor for Rex Harrison.

Though the romance between Eliza and Professor Higgins is more understated compared to other films on this list, “My Fair Lady” remains an iconic Oscar-winning romantic movie for its memorable songs and charming performances.

Why It’s an Iconic Oscar Winner:

• Awards: 8 Oscars, including Best Picture and Best Actor.
• Romantic Highlights: The evolving relationship between Eliza and Professor Higgins, and the unforgettable musical numbers like “I Could Have Danced All Night.”

11. Moonlight (2016)

“Moonlight” is a groundbreaking film that tells the story of Chiron, a young Black man navigating his identity and sexuality in a rough neighborhood of Miami. Directed by Barry Jenkins, the film won 3 Oscars, including Best Picture, and is notable for its tender exploration of love and connection, particularly in the context of Chiron’s relationship with his first love, Kevin.

The film’s poetic storytelling and emotional depth make it a unique entry among Oscar-winning romantic movies, highlighting the complexities of love and self-discovery.

Why It’s an Iconic Oscar Winner:

• Awards: 3 Oscars, including Best Picture and Best Adapted Screenplay.
• Romantic Highlights: The intimate moments shared between Chiron and Kevin, capture the beauty and vulnerability of first love.

12. The Wedding Singer (1998)

A romantic comedy classic, “The Wedding Singer”, starring Adam Sandler and Drew Barrymore, tells the story of Robbie, a wedding singer, who falls for Julia, a waitress, despite her engagement to another man. While the film won no Oscars, it’s frequently celebrated for its romantic elements and nostalgic 1980s setting.

Although not technically an Oscar-winning film, its enduring popularity and iconic romantic moments make it a beloved entry in discussions about romantic comedies.

Why It’s Iconic:

• Popularity: A staple of late ’90s romantic comedies.
• Romantic Highlights: The heartfelt moments between Robbie and Julia, including the unforgettable airport scene where love conquers all.

13. A Beautiful Mind (2001)

“A Beautiful Mind”, directed by Ron Howard, tells the story of John Nash (Russell Crowe), a brilliant mathematician struggling with schizophrenia, and the unwavering support of his wife, Alicia (Jennifer Connelly). The film won 4 Oscars, including Best Picture and Best Supporting Actress for Connelly.

The film beautifully showcases the power of love in the face of adversity, making it a significant entry among Oscar-winning romantic movies.

Why It’s an Iconic Oscar Winner:

• Awards: 4 Oscars, including Best Picture and Best Supporting Actress.
• Romantic Highlights: Alicia’s dedication to John through his struggles, is exemplified in the poignant moments that depict their unwavering bond.

14. The Notebook (2004)

Based on Nicholas Sparks’ novel, “The Notebook” became a modern classic in the romance genre, although it did not win an Oscar. The story chronicles the enduring love between Noah (Ryan Gosling) and Allie (Rachel McAdams) across decades, exploring themes of love, memory, and devotion.

Its emotional depth and unforgettable love story have solidified its place as a staple in discussions of romantic films.

Why It’s Iconic:

• Popularity: A fan-favorite for its heartfelt narrative and iconic scenes.
• Romantic Highlights: The passionate reunion between Noah and Allie, captures the essence of enduring love.

15. Sense and Sensibility (1995)

“Sense and Sensibility,” directed by Ang Lee and based on Jane Austen’s novel, tells the story of the Dashwood sisters as they navigate love and heartbreak in early 19th-century England. The film won an Oscar for Best Adapted Screenplay and is celebrated for its romantic tension and character development.

The rich storytelling and compelling performances by Emma Thompson and Kate Winslet make it a beloved entry among Oscar-winning romantic movies.

Why It’s an Iconic Oscar Winner:

• Awards: 1 Oscar for Best Adapted Screenplay.
• Romantic Highlights: The contrasting love stories of Elinor and Marianne Dashwood, and the moments that capture the subtleties of romance.

16. Crouching Tiger, Hidden Dragon (2000)

“Crouching Tiger, Hidden Dragon,” directed by Ang Lee, is a visually stunning martial arts film that also features a deeply emotional love story. The film won 4 Oscars, including Best Foreign Language Film and Best Cinematography. It explores themes of love, honor, and sacrifice within a rich historical context.

The romantic tension between characters Shu Lien (Michelle Yeoh) and Li Mu Bai (Chow Yun-fat) adds a layer of complexity to the film, making it a unique entry into the realm of Oscar-winning romantic movies.

Why It’s an Iconic Oscar Winner:

• Awards: 4 Oscars, including Best Foreign Language Film.
• Romantic Highlights: The unspoken love between Shu Lien and Li Mu Bai, is underscored by breathtaking visuals and action sequences.

17. West Side Story (1961)

“West Side Story,” a musical adaptation of Shakespeare’s “Romeo and Juliet,” is a timeless classic that won 10 Oscars, including Best Picture and Best Director for Jerome Robbins and Robert Wise. The film tells the story of Tony (Richard Beymer) and Maria (Natalie Wood), whose love faces the challenges of rival gangs in New York City.

With its memorable songs and choreography, “West Side Story” remains a high point in Oscar-winning romantic movies.

Why It’s an Iconic Oscar Winner:

• Awards: 10 Oscars, including Best Picture and Best Director.
• Romantic Highlights: The iconic “Tonight” song and dance sequence encapsulates the passion and tragedy of their love.

18. As Good As It Gets (1997)

Starring Jack Nicholson and Helen Hunt, “As Good As It Gets” is a romantic comedy-drama that won 2 Oscars, including Best Actor for Nicholson and Best Actress for Hunt. The film follows Melvin Udall, an obsessive-compulsive author, as he develops a relationship with a waitress, Carol (Helen Hunt), while also caring for a neighbor’s dog.

Its exploration of love and redemption, paired with strong performances, makes it a noteworthy film in the realm of Oscar-winning romantic movies.

Why It’s an Iconic Oscar Winner:

• Awards: 2 Oscars, including Best Actor and Best Actress.
• Romantic Highlights: The evolution of Melvin and Carol’s relationship, is marked by both comedic and heartfelt moments.

19. Pride & Prejudice (2005)

This adaptation of Jane Austen’s beloved novel, directed by Joe Wright, brings to life the romantic tension between Elizabeth Bennet (Keira Knightley) and Mr. Darcy (Matthew Macfadyen). The film received 4 Oscar nominations and won for Best Original Score.

“Pride & Prejudice” is celebrated for its cinematography, production design, and compelling performances, making it a quintessential entry among Oscar-winning romantic movies.

Why It’s an Iconic Oscar Winner:

• Awards: Nominated for 4 Oscars, winning for Best Original Score.
• Romantic Highlights: The famous scene where Mr. Darcy proposes to Elizabeth, showcases their tumultuous relationship.

20. Silver Linings Playbook (2012)

“Silver Linings Playbook,” directed by David O. Russell, is a romantic comedy-drama that follows Pat (Bradley Cooper) as he tries to rebuild his life after being released from a mental health facility. Along the way, he meets Tiffany (Jennifer Lawrence), a woman grappling with her struggles.

The film won 1 Oscar for Best Actress for Jennifer Lawrence, and its heartfelt exploration of love and mental health issues sets it apart in the category of Oscar-winning romantic movies.

Why It’s an Iconic Oscar Winner:

• Awards: 1 Oscar for Best Actress.
• Romantic Highlights: The chemistry between Pat and Tiffany, is highlighted in their dance sequences and candid conversations.

21. The Artist (2011)

“The Artist,” directed by Michel Hazanavicius, is a silent black-and-white film that pays homage to Hollywood’s golden age. The film won 5 Oscars, including Best Picture, Best Director, and Best Actor for Jean Dujardin. The story revolves around the silent film star George Valentin and his transition to the era of talkies, intertwined with his romantic connection to actress Peppy Miller (Bérénice Bejo).

This unique approach to storytelling and its romantic elements make “The Artist” a standout among Oscar-winning romantic movies.

Why It’s an Iconic Oscar Winner:

• Awards: 5 Oscars, including Best Picture and Best Actor.
• Romantic Highlights: The silent yet expressive moments shared between George and Peppy, showcase the timelessness of love.

22. Call Me by Your Name (2017)

“Call Me by Your Name,” directed by Luca Guadagnino, is a tender coming-of-age romance set in 1980s Italy. The film follows Elio (Timothée Chalamet) and Oliver (Armie Hammer) as they explore their feelings for each other over a summer. The film won an Oscar for Best Adapted Screenplay and is celebrated for its lush cinematography and poignant storytelling.

The film’s exploration of first love, desire, and heartache resonates deeply, making it one of the most celebrated Oscar-winning romantic movies in recent history.

Why It’s an Iconic Oscar Winner:

• Awards: 1 Oscar for Best Adapted Screenplay.
• Romantic Highlights: The iconic peach scene and the tender final moments between Elio and Oliver, encapsulate the bittersweet nature of young love.

Conclusion

This comprehensive list of 22 Oscar-winning romantic Movies showcases the diversity and depth of love stories that have captivated audiences throughout cinema history. From epic romances that span time and tragedy to intimate tales of connection and personal growth, these films not only highlight the magic of love but also the artistry of filmmaking.

Each of these Oscar-winning romantic movies brings something unique to the table, making them not just entertaining but also thought-provoking reflections on love in its many forms. Whether you’re in the mood for a classic or a contemporary tale, this list serves as an excellent guide for your next movie night.