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Battle of the Sexes – Romantic Comedies of the Sixties

Ever since I first saw Cary Grant and Katharine Hepburn in the classic screwball comedy, Bringing Up Baby I have loved romantic comedies. In fact, it is my favorite film genre. There is something about mixing humor with romance that I find entertaining and oh so relate-able.

Romantic comedies tend to be on a circular trend pattern. There are periods of time when they are very popular and other times where there is a dearth of available offerings. Sadly, we seem to be in one of those low points where there just aren’t that many good romantic comedies currently being made. Where is Nora Ephron, patron saint director of romcoms and Meg Ryan when you need them?

RELATED POST: The 100 Best Romantic Comedies of all Time (Part One)

One of the heydays for romantic comedies was in the late nineteen fifties and sixties. It was a time of cultural transition in America as well as a transitional time in American film. The old guard studio system was almost extinct, the darker more serious films of the 1940’s and 1950’s had run their course. Nobody quite knew what type of films to make and which types would be successful in a changing world. This led to some experimental films as well as a return to genres that had been successful in the past.

So, in came the lighter, funnier fare of the romantic comedy of the sixties. Stars such as Jack Lemmon, Debbie Reynolds, James Garner, Natalie Wood, Jane Fonda, Rock Hudson, Sandra Dee, Tony Randall and Audrey Hepburn had great success during this time starring in these romcoms. Of course, the undisputed queen of the romantic comedy is Doris Day who arguably made more of these films than any other actor/actress of this time period.

RELATED POST: The 100 Best Romantic Comedies of all Time (Part Two)

One of the consistent markers of the romantic comedy is the battle between the sexes. There was no better time to explore this, then during the sixties, as women’s roles continued to evolve and grow. I have compiled a list of films from the late 50’s and the 60’s which are some of the best romantic comedy films of their time.


(In no particular order)


Photo Credit: Universal Pictures

Stars: Cary Grant & Doris Day

Day plays an innocent virgin (when did she not?) who draws the attention of Grant’s wealthy businessman when she tries to stand up for herself. They begin a romance, but he is only interested in the short-term and she is holding out for marriage. Will his wealth and generosity sweep away her integrity or will he succumb to her accident-prone innocence?


Photo Credit: 20th Century Fox

Stars: Peter O’Toole & Audrey Hepburn

Hepburn is the daughter of an expert art forger who mistakes an art investigator for an experienced burglar and convinces him to help her steal one of her father’s pieces from a museum display before anyone realizes it is a fake. Will these two amateurs pull off a sophisticated theft? Will she discover that the man who is helping her is the same man hired by the museum to inspect her father’s statue?

RELATED POST: Vintage Film Review: How To Steal a Million (1966) -A Must Watch if You Love Art and Audrey


Photo Credit: Metro-Goldwyn-Mayer

Stars: Jane Fonda, Rod Taylor, and Cliff Robertson

Fonda’s character visits her playboy pilot brother in New York and tells him she believes her virginity is standing in the way of true love. While staying at her brother’s apartment she meets a stranger and is determined to seduce him. Problems ensue when her brother finds out and her ex-fiance shows up. Will this innocent manage a seduction of the stranger she is quickly falling for? Will her brother see the error of his ways when he witnesses his sister’s attempts to lose her innocence?

#4: BOYS NIGHT OUT (1962)

Photo Credit: Kimco Filmways Pictures/Metro-Goldwyn-Mayer

Stars: Kim Novak, James Garner, and perennial third wheel Tony Randall

Four men, three married and one single, agree to the shared arrangement of an apartment with a beautiful blonde in order to spice up their humdrum lives. But she doesn’t tell them that she is using them as a case study for a sociology class. Will she be able to retain her innocence in this shared arrangement? Will they learn that she is simply using them for her study paper?

#5: CHARADE (1963)

Photo Credit: Universal Pictures

Stars: Cary Grant and Audrey Hepburn

Hepburn is a widow who learns that her husband had stolen a fortune with four other men years ago and then double-crossed them and hid the money. Now, those men are after her thinking she has knows where the money is. Grant shows up as an ambiguous character who could be her hero or one of the villains. Will she learn where the money is hidden before one of them kills her? Can she trust Grant’s character who is constantly changing his name? Can I please have the Givenchy wardrobe she wears in this film?


Photo Credit: Metro-Goldwyn-Mayer

Stars: Doris Day and Rod Taylor

Taylor plays the head of a scientific research laboratory who gets off on the wrong foot with Day’s perky widow who is also his employee. He decides to pursue her against the advice of his government collaborators who suspect she may be a Russian spy planted in the company to steal his latest invention. Will a brilliant scientist and his quirky opposite be able to trust each other and find common ground? Will I ever not laugh when watching this movie and its final chase scene?

#7: MCLINTOCK! (1963)

Photo Credit: Batjac Productions/United Artists

Stars: famous frequent co-stars and friends John Wayne and Maureen O’Hara

Wayne and O’Hara play the estranged McClintocks who worked together to settle the west and found a town, but who due to a misunderstanding are at odds with each other. When their daughter returns from college, Mrs. McClintock also returns home for her daughter and for a divorce. Will they be able to work out their differences? Will I ever settle my internal conflict between laughter and offense when McClintock spanks his recalcitrant wife in front of the whole town?


Stars: Doris Day & Jack Lemmon

Day plays a widowed lobster “farmer” whose business is negatively impacted when a railroad delay ruins her lobster shipment to a nearby business. When they refuse to apologize or compensate her loss, she enlists the help of the longtime family friend, secret admirer and attorney Lemmon, to take the railroad to court in this David and Goliath tale. Will this “David” be able to defeat the deep-pockets of the railroad “Goliath”? And, will Lemmon’s lawyer ever work up the courage to tell his favorite lobster farmer how he feels? Will I ever not be moved by the rousing political speech Lemmon gives about American democracy?


Photo Credit: Paramount Pictures

Stars: Robert Redford & Jane Fonda

Redford and Fonda play newlyweds. He is conservative and responsible. She is adventurous and in pursuit of fun. Will they be able to overcome their differences to learn to live together? Has there ever been a more beautiful onscreen couple than Redford and Fonda?


Photo Credit: Warner Bros. Pictures

Stars: Natalie Wood, Tony Curtis, Lauren Bacall & Henry Fonda

Curtis plays a tabloid reporter who pretends to be someone else in order to get an interview with Wood’s famous sex psychologist. Bacall and Fonda are Curtis’ next door neighbors with marriage and sex problems of their own. Will Curtis false identity be discovered? Is Wood’s single psychologist really qualified to counsel on such a topic?

#11: THE MATING GAME (1959)

Stars: Tony Randall & Debbie Reynolds

Randall is an uptight IRS agent sent to audit Reynold’s family who doesn’t believe in paying taxes. But when he meets their innocent and charming daughter, will he be able to separate business from pleasure?

#12: LOVER COME BACK (1961)

Photo Credit: Universal Pictures

Stars: Rock Hudson & Doris Day

Hudson and Day play advertising salespeople who work for competing companies. He uses underhanded methods to secure contracts including accidentally airing a commercial for a product which doesn’t exist. Now he must create the product while she will do her best to steal the non-existent account. Who will win this advertising war? Can competitors become lovers?

#13: FITZWILLY (1967)

Stars: Dick Van Dyke & Barbara Feldon

Van Dyke plays the title character, a butler to an elderly heiress who doesn’t realize she is broke. Fitzwilly and the rest of her staff secretly carry out robberies in order to keep her in the manner to which she is accustomed. Feldon lands in this wacky household as a secretary to the heiress but begins to fall for the butler at the same time as she notices suspicious behavior. Will she expose the thieving yet good-hearted butler?


Photo Credit: Universal Pictures

Stars: Rock Hudson & Paula Prentice

Hudson is a fishing expert, who works in a sporting goods store and has written a best seller on the subject. The only problem is he has never actually been fishing. When his ignorant boss enters him in a fishing contest he must hire an expert to help him learn quickly. He ends up with Prentice, a female fisherman who has the daunting task of teaching this neophyte. Will he be able to learn the basics in time for the tournament? Will she run out of patience before he can learn enough to make him credible?


Photo Credit: Metro-Goldwyn-Mayer

Stars: Steve McQueen

In a rare comedy role, McQueen is a navy lieutenant who, along with some friends, decides to use a classified naval computing machine to break the bank at a Venice casino. His plan is complicated by the fact that his commanding officer is staying at the same casino and McQueen unknowingly falls in love with his daughter. Will he be able to succeed in breaking the bank with the Commander suspicious about the computer and protective of his daughter?

#16: PILLOW TALK (1959)

Photo Credit: Arwin Productions/Universal-International

Stars: Rock Hudson & Doris Day in their second of three pairings

Hudson and Day star in this film about two people who share a phone party line. He is a playboy who is always hogging the line with his romantic endeavors. When her complaints to the phone line go unheeded, she confronts him herself. But when he catches an eyeful of his complaining neighbor will she become his next conquest?

#17: PENELOPE (1966)

Stars: Natalie Wood

Wood plays the title character, a bored and lonely housewife who decides to rob her husband’s bank. As she continues her life of crime she is perplexed by her own motivations. And even though she confesses her crimes to her shrink and a police detective, their attraction to her override their better judgment. Will she ever understand what is driving her to steal things she doesn’t need? What will her husband do when he learns his own wife has robbed his bank?


Stars: Sandra Dee & George Hamilton

Dee is the lead singer in a band with a pushy stage mom for a manager. After a night spent with the rigid, uptight Hamilton leaves her pregnant, she decides to pursue her real dream of being a wife and mother. However, he doesn’t even know she is pregnant and she has three other men interested in being her baby daddy. Which man will she choose? Will Hamilton ever relax enough to let her into his life?

#19: CAT BALLOU (1965)

Photo Credit: Harold Hecht Productions/Columbia Pictures

Stars: Jane Fonda

Jane Fonda is the title character, an innocent woman seeking to avenge her father’s death and save his ranch. She hires a drunken gunslinger to help her achieve her aims and ends up collecting a few other ne’er do wells along with him. But can an innocent truly follow through on killing her father’s killer? Will any of the suspicious characters protecting her wind up winning her heart?


Stars: James Garner & Joan Hackett

Just passing through an Old West town, Garner’s character is headed to the gold fields. In need of money, he is convinced to become sheriff in this town terrorized by outlaws. He is a man who tends to take the easy way out and has no intention of sticking around long term. But the mayor’s daughter may have a thing or two to say about that. Will Garner be able to tame this wild West town? Will the mayor’s daughter be able to tame this wandering man?

Have you seen any of these films? What are some of your favorite romantic comedies from the late fifties and sixties? 

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By on June 21st, 2017

About Brittaney B.

Brittaney has had her head in the clouds ever since she first fell in love with books and film as a young child. She's a firm believer in the power of story to transport us to new places while also transforming our hearts. She tends to favor historical fiction and classic films since they also allow her to feel like a time traveler. Brittaney is a native resident of Texas and has been honing her own ability to write and tell stories for many years now. You can find more of her wordsmith skills at her website www.storyenthusiast.com.

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5 thoughts on “Battle of the Sexes – Romantic Comedies of the Sixties”

  1. I was wondering if you’d talk about my favorite of these films and you talked about it first! The 50s-60s has been my most favorite romcom period hands down and That Touch of Mink tops them all for me.

    Not only the performances of Day and Grant but also Gig Young as Roger make this movie so enjoyable.

    Great list!

    • You can never go wrong with a Cary Grant or Doris Day comedy. But I think Gig Young may just steal this film out from under them. His story line and character are hilarious!

  2. My…My!!! Doris Day, Rock Hudson, Tony Randall was the epitome of 50 and 60 romantic comedy…. love it… When my grandfather introduced me to TCM as a child, I became hooked and now most of my movie collection consists of classic movies from the 30s and beyond!

    I was first introduced to “The Duke” through McClintock and I fell in love, the seeing Rock Hudson, Cary Grant…. whewwww. I see some movies that include some of my favorite stars I have yet to see. Thanks SPR!

  3. Agree also should include Donovans Reef with John Wayne, Come September with Rock Hudson and Gina Lollobrigida, and The Rare Breed with James Stewart and Maureen O’Hara


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