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Best 11 Romantic Comedies of the 1960s: A Look Back at the Classics

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Here are the most captivating and enchanting 60s romantic comedies, ranked from the absolute pinnacle to the slightly less exceptional. These films have transcended time, becoming timeless classics that continue to captivate audiences today. Each one played a pivotal role in shaping the era, leaving an indelible mark on cinematic history.

Prepare to be swept away by the iconic Breakfast at Tiffany’s from 1961. Audrey Hepburn’s portrayal of the beguiling society girl, Holly Golightly, is an absolute delight that has left an everlasting impression on viewers. This romantic comedy even secured two coveted Oscars for Best Score and Best Original Song with the enchanting “Moon River.” Another gem from the 60s is The Apartment, a captivating tale following a young playboy, played by the charismatic Michael Caine, as he navigates encounters with various captivating women, ultimately discovering the true meaning of loneliness.

But wait, there’s more! Brace yourself for the enthralling Charade, the delightful Barefoot in the Park, and the dazzling Viva Las Vegas. These movies have all earned their rightful place on this list, each contributing something unique and extraordinary to the tapestry of 60s romantic comedies.

Now, we eagerly turn to you, our cherished readers, for your invaluable insights. Which of these mesmerizing 1960s romantic comedies do you believe reigns supreme? We implore you to show your appreciation by giving a resounding cheer to your favorites!

Please be aware that one film on this list tends to ignite spirited debates: Blue Hawaii.

1. Charade

Regina Lampert, played by Audrey Hepburn, finds herself captivated by the charming Peter Joshua, portrayed by Cary Grant, during a skiing trip in the beautiful French Alps. However, her joy is short-lived as she returns to Paris to the devastating news of her husband’s murder. Little does she know that this is just the beginning of a thrilling adventure.

Joined by Peter, Regina embarks on a journey to catch three of her late husband’s comrades from World War II: Tex, Scobie, and Gideon. These men are on a relentless pursuit of a whopping quarter of a million dollars that the quartet had stolen during their time behind enemy lines. But here’s the twist – why does Peter keep changing his name?

This suspenseful story will keep you on the edge of your seat as Regina and Peter chase after the money and uncover the truth behind Peter’s mysterious identity. Get ready for an exhilarating ride filled with unexpected turns and thrilling encounters.

Released: 1963
Directed by: Stanley Donen
Actors: Cary Grant, Audrey Hepburn, Walter Matthau

2. Breakfast at Tiffany’s

Breakfast at Tiffany's
In the classic romantic comedy, Breakfast at Tiffany’s, we follow the story of Holly Golightly, played by the captivating Audrey Hepburn. Holly is a young woman living an intriguingly carefree lifestyle in the bustling streets of New York City. Alongside her, we have George Peppard as Paul Varjak, a struggling writer who becomes captivated by Holly’s elusive charm. Set against the vibrant backdrop of 1960s Manhattan, the film delves into their blossoming relationship.

Filled with memorable moments and iconic fashion statements, Breakfast at Tiffany’s is a cinematic masterpiece that has stood the test of time. This movie achieved great recognition, earning two Academy Awards and capturing the hearts of many. Its charm goes beyond the enchanting romance it portrays; it also offers a commentary on societal norms and expectations, adding depth to its storyline.

Released: 1961
Directed by: Blake Edwards
Actors: Audrey Hepburn, George Peppard, Patricia Neal

3. Move Over, Darling

Move Over, Darling
Nicholas Arden, played by James Garner, has been grappling with the void left by his wife, Ellen, portrayed by Doris Day. However, it appears that Ellen is no more after a tragic plane crash. In an attempt to move forward, Nicholas decides to remarry. Polly Bergen’s character, Bianca Steele, becomes his wife five years after Ellen’s disappearance. Little does Nicholas know, Ellen is actually alive.

After being rescued from the island where she was stranded, Ellen rushes to piece together the life she lost when her plane went down at sea.

Released: 1963
Directed by: Michael Gordon
Actors: Doris Day, James Garner, Polly Bergen

4. The Thrill of It All

The Thrill of It All
Successful OB-GYN Gerald Boyer, played by James Garner, and his wife Beverly, portrayed by Doris Day, have a blissful marriage and are proud parents of two children. During a dinner gathering, Beverly excitedly talks about her love for Happy Soap, her favorite soap brand, and how it brings her joy. Unexpectedly, she crosses paths with the owner of the company and is promptly offered a contract to become the face of Happy Soap in television commercials. Although Beverly is thrilled about this opportunity, Gerald struggles to come to terms with his wife’s sudden fame. In an attempt to maintain their traditional domestic life, he devises a plan to sabotage Beverly’s burgeoning career.

Released: 1963
Directed by: Norman Jewison
Actors: Doris Day, James Garner, Arlene Francis

5. How to Steal a Million

How to Steal a Million
Charles Bonnet, played by Hugh Griffith, has a unique way of showing his love for art – by creating fake masterpieces and selling them for a pretty penny. However, things take a turn for the worse when one of his replicated sculptures ends up in a renowned museum in Paris. If the experts find out that it’s a fake, Bonnet’s reputation will suffer a major blow. To prevent this catastrophe, his daughter Nicole, portrayed by Audrey Hepburn, enlists the help of a skilled cat burglar named Simon Dermott, played by Peter O’Toole. Their mission: to reclaim the stolen sculpture before it’s too late.

Released: 1966
Directed by: William Wyler
Actors: Audrey Hepburn, Peter O’Toole, Eli Wallach

6. That Touch of Mink

That Touch of Mink
Cathy Timberlake, played by Doris Day, is on her way to a job interview when she gets splattered with mud by a car carrying businessman Philip Shayne, played by Cary Grant. Philip feels bad about the incident and sends his assistant, Roger (Gig Young), to apologize. However, when Roger meets Cathy, he realizes that she could be a good match for his boss.

Although Cathy and Philip are attracted to each other, they have different desires. Philip is looking for a casual fling, while Cathy dreams of a long-term commitment in marriage. As they embark on their journey to various exotic places, their conflicting aspirations are put to the test.

Released: 1962
Directed by: Delbert Mann
Actors: Cary Grant, Doris Day, Gig Young

7. The Apartment

The Apartment
In the classic black-and-white film, The Apartment, we meet C.C. Baxter (played by Jack Lemmon), a modest insurance clerk who cleverly allows his bosses to use his apartment for their secret affairs as a way to get ahead in his career. However, his life takes an unexpected turn when he falls for Fran Kubelik (portrayed by Shirley MacLaine), an elevator operator who happens to be the mistress of his boss, Jeff D. Sheldrake (played by Fred MacMurray). This drama-comedy from the 1960s, directed by the talented Billy Wilder, achieved great success by winning five Academy Awards, including Best Picture and Best Director. The film skillfully combines elements of romance, humor, and a touch of melancholy, all while delving into the themes of ambition and betrayal.

Released: 1960
Directed by: Billy Wilder
Actors: Jack Lemmon, Shirley MacLaine, Fred MacMurray

8. Send Me No Flowers

Send Me No Flowers
George, a middle-aged hypochondriac, overhears his doctors chatting about another patient. Jumping to conclusions, he convinces himself that he’s terminally ill during his hospital visit. With the belief that his days are numbered, George turns to his friend Arnold for assistance. Together, they embark on a mission to find a new husband for George’s wife, Judy.

After weighing their options, George and Arnold settle on Bert, a prosperous businessman. However, George’s peculiar actions raise suspicions in Judy’s mind. She begins to suspect that he might be concealing an affair.

In this story, George’s eavesdropping escapade leads him to falsely believe he is facing a terminal illness. Prompted by this misconception, he enlists the help of his friend Arnold to find Judy a new husband. Despite their efforts, Judy becomes wary of George’s strange behavior, suspecting that he may be hiding an extramarital affair.

Released: 1964
Directed by: Norman Jewison
Actors: Rock Hudson, Doris Day, Tony Randall

9. Barefoot in the Park

Barefoot in the Park
In this film, which is based on a Neil Simon play, we meet Corie and Paul Bratter, a newly married couple. Corie is described as a free spirit, while Paul is an uptight lawyer. They both live in a sixth-floor apartment in Greenwich Village, and that’s where the story begins to unfold.

After their marriage, Corie feels the need to find a companion for her mother, Ethel, who is now alone. So, she decides to set her up with their neighbor, Victor. Ethel is played by the talented Mildred Natwick, and Victor is portrayed by Charles Boyer.

However, things start to go awry when some inappropriate behavior occurs during a double date involving Corie, Paul, Ethel, and Victor. This incident sparks conflict between the young couple, and the idea of divorce begins to enter their minds.

As the plot progresses, we are taken on a journey filled with laughter, drama, and self-discovery. Will Corie and Paul be able to overcome their differences and save their marriage? That’s the question that keeps us hooked until the very end.

Released: 1967
Directed by: Gene Saks
Actors: Robert Redford, Jane Fonda, Charles Boyer

10. Lover Come Back

Lover Come Back
Jerry is a smooth-talking adman who knows how to work his way around women and alcohol to win over his clients. However, his tactics catch the attention of Carol, an executive at a competing agency, who isn’t too thrilled with his approach. Carol decides to report Jerry to the Ad Council, raising some serious concerns.

To counter Carol’s accusations, Jerry cleverly uses the testimony of a nightclub performer named Edie Adams, whom he bribes with a leading role in a phony ad campaign. This diversion helps him steer clear of trouble, or so he thinks. Little does he know that his clueless boss, played by Tony Randall, goes ahead and airs one of the ads on television, causing a whole new set of problems for Jerry.

Now, Jerry is left with no choice but to come up with a brand-new product to salvage the situation. It seems like his slick ways have finally caught up with him, and he must find a way to navigate this unexpected turn of events.

Released: 1961
Directed by: Delbert Mann
Actors: Rock Hudson, Doris Day, Tony Randall

11. Paris When It Sizzles

Paris When It Sizzles
Hotshot Hollywood screenwriter Richard Benson, played by William Holden, finds himself in a bit of a bind. He managed to sell a script idea to the decadent producer Alexander Meyerheim, portrayed by Noel Coward. However, instead of diligently working on the screenplay, Benson has been gallivanting around Paris, squandering his precious time.

As the deadline looms just a couple of days away, Benson is thrown a lifeline in the form of a new assistant, Gabrielle Simpson, played by Audrey Hepburn. With her help, he embarks on the task of piecing together a love story by acting out various scenarios. Gabrielle’s involvement in the process proves to be instrumental in shaping the narrative.

However, as the saying goes, life has a funny way of imitating art. The lines between fiction and reality begin to blur for Benson and Gabrielle, leading to unforeseen consequences. The boundaries between their work and personal lives become increasingly hazy, and they find themselves caught up in a whirlwind of emotions.

In this captivating story, Richard Benson’s journey from a troubled screenwriter to one who finds inspiration through unconventional means is beautifully brought to life by the talented cast. With the charming chemistry between William Holden and Audrey Hepburn, viewers are treated to a delightful exploration of the creative process and its impact on the lives of those involved.

So, join Benson and Simpson on this rollercoaster ride as they navigate the challenges of the film industry, discover the power of love, and learn that sometimes, the best stories are the ones we live ourselves.

Released: 1964
Directed by: Richard Quine
Actors: William Holden, Audrey Hepburn, Noel Coward

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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