NewsNewsBest 11 Romantic Comedies from the 1950s: A Year...

Best 11 Romantic Comedies from the 1950s: A Year 2023 Guide

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The 1950s is often seen as a time of traditional family values, but let’s not forget the enchanting love stories that captivated audiences. It was a decade that brought us some of the most unforgettable romantic comedies ever made. These heartwarming films transported us into worlds where opposites collided and love triangles kept us on the edge of our seats. The silver screen was graced by legendary actors and actresses who etched their names into cinematic history.

One film that shines brightly among the best ’50s romantic comedies is the timeless animated classic, Lady and the Tramp. Don’t be fooled by its furry protagonists, this delightful movie will have you laughing and falling in love with its universal charm. The talented Peggy Lee lent her voice to this Disney masterpiece, adding another layer of magic. Meanwhile, the radiant Audrey Hepburn established herself as a true romantic icon with captivating performances in Funny Face, Sabrina, and Roman Holiday. And who could forget the enchanting Marilyn Monroe? Her magnetic allure and irresistible charm lit up the screen in Gentlemen Prefer Blondes and The Seven Year Itch.

Now, it’s time for you to embark on a journey through the golden age of romantic comedies and discover which film deserves the crown of the greatest from the 1950s. So grab your popcorn, immerse yourself in these cinematic gems, and let your voice be heard as you embrace the joy and wonder of these unforgettable tales.

1. Singin’ in the Rain

Singin' in the Rain
During the heyday of Hollywood, Singin’ in the Rain emerged as a delightful musical that gracefully navigates the transition from silent movies to talkies. Don Lockwood (played by Gene Kelly), a beloved star of silent films, finds himself grappling with the seismic changes in the industry. Alongside him is his co-star Lina Lamont (played by Jean Hagen), whose voice has the ability to shatter glass. However, hope arrives in the form of Kathy Selden (played by Debbie Reynolds), an aspiring actress who not only becomes Don’s love interest but also his savior. With its iconic dance sequences and catchy tunes, the film rightfully earned Jean Hagen a Golden Globe and has solidified its place as a timeless classic in cinematic history.

Released: 1952
Directed by: Stanley Donen, Gene Kelly
Actors: Gene Kelly, Debbie Reynolds, Donald O’Connor

2. Roman Holiday

Roman Holiday
The 1953 romantic comedy, Roman Holiday, is an absolute delight. It tells the story of Princess Ann (played by Audrey Hepburn), who decides to take a break from her royal responsibilities and venture out into Rome by herself. It’s during her solo exploration that she crosses paths with Joe Bradley (played by Gregory Peck), an American journalist who realizes her true identity and sees a potential big story in the making. Little did Ann know about Joe’s profession, so she simply enjoys the little pleasures of everyday life.

This movie received well-deserved recognition, winning three Academy Awards. Audrey Hepburn, in her first major film role, was awarded the Best Actress accolade. It’s truly heartwarming to see this film skillfully blend elements of romance and adventure into a timeless piece of entertainment.

Released: 1953
Directed by: William Wyler
Actors: Gregory Peck, Audrey Hepburn, Eddie Albert

3. Sabrina

Sabrina, the daughter of a chauffeur, comes back home after spending two years in Paris. She has blossomed into a stunning young woman and immediately grabs the attention of David, the carefree son of her father’s wealthy employers. It turns out that Sabrina has always had feelings for David, and he starts charming her in return.

However, their budding romance faces a hurdle in the form of Linus, David’s older brother. Linus is the serious type, responsible for running the family business. He has pinned his hopes on David marrying a wealthy heiress to ensure a crucial merger goes through. This puts a strain on the relationship between David and Sabrina, as Linus’s plans clash with their love for each other.

Released: 1954
Directed by: Billy Wilder
Actors: Humphrey Bogart, Audrey Hepburn, William Holden

4. Pillow Talk

Pillow Talk
Playboy songwriter Brad Allen, played by Rock Hudson, has a habit of getting involved in multiple romances. This constant stream of relationships annoys his neighbor, interior designer Jan Morrow, portrayed by Doris Day. The reason for her annoyance? Well, they share a telephone party line, and Jan gets an earful of Brad’s smooth talking on a regular basis. Frustrated with the situation, Jan tries to complain but doesn’t get any satisfaction.

Determined to win her over, Brad decides to adopt the persona of a sincere and upstanding Texas rancher. He plans to seduce Jan while hiding his true intentions. However, things get complicated when their mutual friend Jonathan, played by Tony Randall, discovers Brad’s true motives. Jonathan also happens to have feelings for Jan, and this revelation leads to some serious conflict between the two friends.

So, as you can imagine, sparks start to fly as Brad’s pursuit of Jan begins. Will he be successful in his seduction, or will Jan see through his charade? And what will happen to the friendship between Brad and Jonathan, now that they both have their sights set on the same woman? Stay tuned to find out!

Released: 1959
Directed by: Michael Gordon
Actors: Rock Hudson, Doris Day, Tony Randall

5. Some Like It Hot

Some Like It Hot
Let’s talk about the classic comedy Some Like It Hot. It’s a hilarious movie where two musicians, Joe and Jerry, are being chased by mobsters in Chicago. So, what’s their brilliant plan to escape? They decide to dress up as women and join an all-female band that’s heading to sunny Florida. Sounds like a wild adventure, right?

As they dive deeper into their charade, Joe finds himself falling head over heels for the seductive Sugar Kane, played by the iconic Marilyn Monroe. Meanwhile, poor Jerry has to deal with a persistent admirer who just won’t leave him alone. Talk about adding more chaos to their already complicated situation!

Directed by the talented Billy Wilder and released in 1959, this film is known for its impeccable comedic timing and sharp script. No wonder it won an Academy Award for Best Costume Design. So, if you’re in the mood for some laughs and clever storytelling, Some Like It Hot is definitely a movie you don’t want to miss.

Released: 1959
Directed by: Billy Wilder
Actors: Tony Curtis, Jack Lemmon, Marilyn Monroe

6. Lady and the Tramp

Lady and the Tramp
In the beloved Disney classic, Lady and the Tramp, we meet Lady, a sophisticated Cocker Spaniel, whose cozy life gets turned upside down. Along comes Tramp, a street-smart mutt with a heart of gold. Their worlds collide, and amidst the vibrant setting of turn-of-the-century America, an unexpected love story begins to unfold. This delightful animated film effortlessly blends romance and adventure, leaving a lasting impression on audiences worldwide. With its unforgettable songs and lovable characters, Lady and the Tramp tackles themes of social inequality and acceptance in a way that remains light-hearted and hopeful. It’s a timeless tale that continues to capture the hearts of each new generation, showcasing Disney’s unmatched storytelling prowess.

Released: 1955
Directed by: Clyde Geronimi, Wilfred Jackson, Hamilton Luske
Actors: Peggy Lee, Barbara Luddy, Larry Roberts

7. How to Marry a Millionaire

How to Marry a Millionaire
Schatze Page, Loco Dempsey, and Pola Debevoise, played by Lauren Bacall, Betty Grable, and Marilyn Monroe respectively, are three women with a mission: finding a millionaire to marry. To achieve this goal, they relocate to a posh apartment in New York City and set out to charm the city’s upper crust. While they have no trouble attracting wealthy suitors, they soon discover that many of them are either unsavory characters or swindlers. At some point, they are faced with a critical choice: prioritize a life of opulence or pursue genuine love?

Released: 1953
Directed by: Jean Negulesco
Actors: Marilyn Monroe, Lauren Bacall, Betty Grable

8. Gentlemen Prefer Blondes

Gentlemen Prefer Blondes
Lorelei Lee, played by Marilyn Monroe, is an absolutely stunning showgirl. She’s got a wedding on the horizon with the well-off Gus Esmond, which doesn’t sit too well with Gus’ wealthy father, Esmond Sr. He’s convinced that Lorelei is only interested in his son’s money. To keep an eye on her, Esmond Sr. hires Ernie Malone, a private detective, to tail Lorelei during her cruise with her best friend, Dorothy Shaw, played by Jane Russell. The goal? Uncover any shady behavior that would put a damper on the upcoming nuptials.

Released: 1953
Directed by: Howard Hawks
Actors: Jane Russell, Marilyn Monroe, Charles Coburn

9. Funny Face

Funny Face
Dick Avery, a fashion photographer from New York City, finds himself captivated by the stunning Jo Stockton, a quiet bookstore employee whom he unintentionally photographs. He sees her as a potential successful model and convinces her to accompany him to France. Together, they embark on a journey through the picturesque streets of Paris, with Dick capturing more breathtaking shots of Jo against famous landmarks. As their bond deepens, they encounter obstacles that threaten their budding relationship.

Released: 1957
Directed by: Stanley Donen
Actors: Audrey Hepburn, Fred Astaire, Kay Thompson

10. The Quiet Man

The Quiet Man
After accidentally causing the death of his opponent during a boxing match, Sean Thornton decides to leave America and go back to his homeland in Ireland. His intention is to purchase his family’s homestead and find solace there. However, this plan takes an unexpected turn when he crosses paths with Will Danaher, who has always harbored a desire for the property. Will, out of spite, strongly opposes the budding romance between his spirited sister, Mary Kate, and Sean, and he flatly refuses to release her dowry. In response, Mary Kate refuses to consummate their marriage until Sean retrieves the money.

Released: 1952
Directed by: John Ford
Actors: John Wayne, Maureen O’Hara, Barry Fitzgerald

11. High Society

High Society
Jazz artist C.K. Dexter Haven, played by Bing Crosby, just can’t seem to get over his ex-wife and neighbor, socialite Tracy Samantha Lord, portrayed by Grace Kelly. The problem is, Tracy is already engaged to someone else, John Lund. But wait, it gets even more complicated! A magazine reporter, played by Frank Sinatra, arrives in town to cover Tracy’s wedding and ends up falling for her too. As Tracy struggles to choose the perfect husband, both men try their best to convince her that they’re the right choice.

Released: 1956
Directed by: Charles Walters
Actors: Bing Crosby, Grace Kelly, Frank Sinatra

Michael Bennett
Michael Bennett
With over 5 years of experience, Michael Bennett is an experienced entertainment blogger recognized for straightforward reviews. His research expertise and thoughtfully crafted blog posts make him a source for readers seeking movie and tv show recommendations.


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