Can You Name These 1950s Rom-Coms?

By: Ian Fortey
Estimated Completion Time
5 min
Can You Name These 1950s Rom-Coms?
Image: Paramount Pictures

About This Quiz

Romance and comedy have a long history together. The melding of genres isn't new by any means, and you could argue Shakespeare was an accomplished rom-com writer in his time. If he were around in the '50s, he totally would have been down for "Gentlemen Prefer Blondes." It makes sense since both comedy and romance are meant to make you feel good and who doesn't enjoy a laugh with the person they love, right? They're pretty much made for each other. That's why "Pillow Talk" was such a big hit!

The '50s weren't the decade that created rom-coms as a genre by any means. In fact, a couple of movies that date all the way back to 1924 are arguably the first romantic comedy films ever made — "Girl Shy" and "Sherlock, Jr." Those were both silent films, so they really had to push the genre to get them to work, but they do fit the mold. By the 1950s, we were fully immersed in some of the greatest rom-coms in film history featuring talents like Marilyn Monroe, Audrey Hepburn, Frank Sinatra and more. If you want a solid, unforgettable romantic comedy, you go to the '50s. So let's see how many of that decade's best you can ID!

17 - Gidget Do you know which of these movies featured a lot of surfing?
"Gidget"
Sandra Dee starred as "Gidget," all about her time as part of the world of surfing which including falling in love with a surfer. This is arguably the first true "beach" movie that became something of a sub-genre for a few years.
"The Matchmaker"
"Here Comes the Groom"
"The Honeymoon"

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2 - Pillow Talk Which Academy Award-winning rom-com made over $18 million at the box office in 1959?
"Pillow Talk"
"Pillow Talk" was the first of three movies that Rock Hudson, Tony Randall and Doris Day made together. It pulled in $18,500,000 at the box office, which, adjusted for inflation, is about $163 million today.
"High Society"
"The Seven Year Itch"
"Desk Set

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10 - How to Marry a Millionaire Lauren Bacall, Betty Grable and Marilyn Monroe all starred in what film?
"The Bridal Path"
"How to Marry a Millionaire"
"How to Marry a Millionaire" featured Grable, Monroe and Bacall as a trio of golddiggers looking to hook up with rich men. It was the first movie ever to be shown in color on TV several years after its release in 1961.
"Dream Wife"
"Spring in Berlin"

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16 - Father of the Bride Steve Martin starred in a remake of this movie. What is it?
"Our Girl Friday"
"Father of the Bride"
"Father of the Bride" featured Liz Tayor and Spencer Tracy as the titular bride and her father. Tracy wanted to have Katharine Hepburn playing his wife in the movie, but apparently the studio felt they made too hot a couple to believed as one that already had raised a family.
"The Tender Trap"
"Designing Woman"

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7 - The Seven Year Itch Which movie features the world-famous image of Marilyn Monroe in a white dress over a subway grate?
"Designing Woman"
"The Seven Year Itch"
"The Seven Year Itch" featured Marilyn Monroe and Tom Ewell. The name of the movie refers to the idea that a man starts losing interest in his wife after seven years of marriage and is actually a term you'll hear psychologists use.
"High Society"
"Funny Face"

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14 - The Quiet Man Do you know which rom-com starred John Wayne?
"Love is Better Than Ever"
"Three Guys Named Mike"
"The Quiet Man"
Not known for romance or comedy much at all, John Wayne took a risk leaving Westerns to make "The Quiet Man" as did director John Ford. The movie was a total shot in the dark at the time, but it won Ford an Oscar for Best Director.
"Roman Holiday"

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33 - Tammy and the Bachelor Do you know now which of these was the first of four movies featuring the main character?
"Houseboat"
"Pillowtalk"
"Irene in Trouble"
"Tammy and the Bachelor"
Debbie Reynolds starred as Tambrey Tyree, aka Tammy, in four separate movies, including "Tammy and the Bachelor." Tammy is a bit of what you might call a rustic tomboy insofar as she runs around the swamp in bare feet and is best friends with a goat.

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19 - Gigi Which of these movies did Audrey Hepburn turn down?
"Gigi"
The movie "Gigi" featured Leslie Caron in the title role of Gig, though, in fact, her character's proper name was Gilberte, which was also the name of one of the two main nerds from "Revenge of the Nerds." Not the cutest name, overall.
"Bell, Book and Candle"
"The Statesman"
"Longshot"

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1 - Some Like it Hot This film has been voted the greatest comedy of all time more than once. Do you know what it is?
"Gentlemen Marry Brunettes"
"The Tender Trap"
"Some Like it Hot"
"Some Like it Hot" was a massive success and featured Tony Curtis, Jack Lemmon and, of course, Marilyn Monroe. Monroe was already quite famous at the time the movie was made, and the director hadn't expected someone of her caliber to want in.
"Dream Wife"

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20 - Kiss Me Kate This movie is based on a play by Shakespeare. What is it?
"The Farmer Takes a Wife"
"Long Gone"
"Kiss Me Kate"
"Kiss Me Kate" is an adaptation of William Shakspeare's "The Taming of the Shrew." In a remarkable departure from how modern films save the technology for action blockbusters, this movie was actually filmed in 3-D.
"She Said Yes"

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13 - Lady and the Tramp This movie was based on an article from "Cosmopolitan" magazine. What is it?
"Lady and the Tramp"
One of Disney's best-loved movies and, despite being animated, clearly a romantic comedy, "Lady and the Tramp" came out in 1955. In 1945, an article in Cosmo entitled "Happy Dan, the Cynical Dog" caught Walt Disney's eye and became the basis for the film.
"The Aristocats"
"All Dogs Go to Heaven"
"101 Dalmatians"

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23 - The Tender Trap Do you know which movie featured Frank Sinatra and Debbie Reynolds?
"The Tender Trap"
Frank Sinatra performed the song "Love is the Tender Trap" from the movie "The Tender Trap" twice in the movie, while Debbie Reynolds actually sings it once in the movie herself, though her version gets criticized by Sinatra on screen.
"The Happy Years"
"Guest House"
"Born to be Loved"

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28 - Bus Stop This movie was one of Marilyn Monroe's more dramatic features. What was it called?
"Bus Stop"
"Bus Stop" was still a comedy and even partially a musical, but it offered up a little more drama than most of Marilyn Monroe's previous films had. Monroe put a lot of effort into making her character different from previous roles, including learning a new accent and deliberately being less impressive with her singing and dancing.
"Meet Me After the Show"
"Confusion"
"The Other Road"

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35 - Funny Face Do you know which of these was Audrey Hepburn's first musical?
"Tammy"
"The Lady Takesa Flyer"
"Royal Wedding"
"Funny Face"
in "Funny Face" Audrey Hepburn sang all of her own musical numbers, unlike in "My Fair Lady," which she made in 1964. She had a solo number as well as a duet with Fred Astaire, who was actually about 30 years her senior at the time.

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31 - Bell Book and Candle This movie is about a witch. What is it?
"Indiscreet"
"Brandy for the Parson"
"The Quiet Man"
"Bell, Book and Candle"
"Bell, Book and Candle" featured Kim Novak as a witch who casts a spell on hew neighbor, played by Jimmy Stewart. The movie also featured a cat named Pyewacket, which was the name of a witch's familiar as described by Witchfinder General Matthew Hopkins in 1644.

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3 - Indiscreet Do you know which of these films featured Ingrid Bergman?
"Adorable Creatures"
"It's Always Fair Weather"
"Girls for the Summer"
"Indiscreet"
"Indiscreet" featured Cary Grant and Ingrid Bergman in the lead roles, but they weren't the original choices for the roles. Clark Gable was lined up for the male lead while the female lead was going to be either Jayne Mansfield or Marilyn Monroe. Just like today, however, casting doesn't always work as planned.

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36 - Dream Wife A character from this movie ended up on the show "I Dream of Jeannie" once. What was it?
"Desk Set"
"Dream Wife"
"Dream Wife" was directed by Sidney Sheldon, who later found fame on TV with the show "I Dream of Jeannie" among several others. He liked the character of Princess Tarji from "Dream Wife" so much that she appeared on a 1966 episode of his show, albeit played by a different actress.
"Easy to Love"
"Stefanie"

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6 - Desk Set This movie was called "His Other Woman" in the UK. What was it the US?
"Kismet"
"Left Right and Center"
"The Silken Affair"
"Desk Set"
"Desk Set" came out in 1957and set Katharine Hepburn at odds with a computer that was invented by the romantic lead Spencer Tracy. This was actually the eighth movie Tracy and Hepburn made together.

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18 - Gentleman Prefer Blondes Which film featured Marilyn Monroe in one of her most iconic roles?
"Gentleman Prefer Blondes"
"Gentlemen Prefer Blondes" came out in 1953, and you can still see its influence in pop culture today. Marylin Monroe's pink dress and performance of the song "Diamonds are a Girl's Best Friend" has been parodied or done in homage by numerous singers from Madonna to Beyonce.
"Teacher's Pet"
"Here Comes the Groom"
"Dream Wife"

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8 - Sabrina This movie featured Humphrey Bogart as the romantic lead. What was it?
"Sabrina"
Cary Grant was initially supposed to star alongside Hepburn in "Sabrina," but he turned it down and Humphrey Bogart got the role. Bogart had spent most of his career in tough-guy roles, so a rom-com was a definite about-face from his usual roles.
"Gigi"
"Let's Do It Again"
"The Moon is Blue"

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40 - Love is Better Than Ever Liz Taylor played the owner of a dance school in this film. What was it?
"Sabrina"
"Gidget"
"Kiss Me Kate"
"Love is Better Than Ever"
"Love is Better Than Ever" came out in 1952 starring Liz Taylor and Larry Parks. If you look closely, you'll see the director Stanley Donen and Gene Kelly both had cameos in the movie as patrons at a restaurant.

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15 - High Society Which film was a musical remake of "The Philadelphia Story"?
"Funny Face"
"Singin' in the Rain"
"Guys and Dolls"
"High Society"
"High Society" starred Bing Crosby, Frank Sinatra and Grace Kelly. This was actually the last movie Grace Kelly starred in before she decided on a career change and became the Princess of Monaco.

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26 - Love Island Which movie cast Eva Gabor as a Balinese native?
"Ground for Marriage"
"Love in the Afternoon"
"Love Island"
Directed by Bud Pollard, a man known for exploitation films, "Love Island" was about a Navy pilot landing on an island and falling in love with a native girl. The movie used a lot of footage that had been shot for an entirely different film called "Legong: Dance of the Virgins."
"Don't Forget Love"

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21 - Kiss Them For Me Which movie was the first big-screen appearance of model Suzy Parker?
"Kiss Them For Me"
"Kiss Them For Me" featured Suzy Parker, who for a time was one of the biggest models in the world, alongside Jayne Mansfield and Cary Grant. The movie did fairly poorly and actually tanked Jayne Mansfield's career for several years.
"About Time"
"Pillow Talk"
"Three Sisters"

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24 - The Farmer Takes a Wife This was a remake of a 1935 movie. What is it?
"The Mating Game"
"Risky Business"
"The Farmer Takes a Wife"
"The Farmer Takes a Wife" came out in 1953 and starred Betty Grable and Dale Robertson. It was a remake of a movie by the same name that came out 18 years prior and starred Henry Fonda and Janet Gaynor.
"Fancy Pants"

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5 - Love in the Afternoon Which film featured Audrey Hepburn in love with a man nearly 30 years her senior?
"Love in the Afternoon"
"Love in the Afternoon" stared Audrey Hepburn and Gary Cooper and followed a bit of a convoluted story of Hepburn first trying to save Cooper's life and then falling in love with him. At the time, Hepburn was 28 and Cooper was 56.
"Gidget"
"Abundance of Life"
"It Should Happen to You"

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11 - Pat and Mike You can watch Katharine Hepburn play golf and tennis in what movie?
"Bus Stop"
"Here Comes the Groom"
"Pat and Mike"
In real life, Katharine Hepburn was an avid sports fan and athlete herself. The golf and tennis featured in "Pat and Mike" weren't shot with a stand-in; it was Hepburn herself playing everything.
"Love in the Afternoon"

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27 - Gentlemen Marry Brunettes This movie almost starred Marilyn Monroe, but it ended up not featuring her. What is it?
"Key to the City"
"Always With You"
"Gentlemen Marry Brunettes"
Not quite a sequel to "Gentlemen Prefer Blondes," "Gentlemen Marry Brunettes" was based on a book by the author of the original which featured Marilyn Monroe and Jane Russell. Russell returned for this movie, playing a different character, but Monroe did not.
"Daddy Long Legs"

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12 - Born Yesterday Which movie was remade in 1993 with Don Johnson, John Goodman and Melanie Griffith?
"Ain't Misbehavin'"
"It Should Happen to You"
"Dream Wife"
"Born Yesterday"
"Born Yesterday" featured Judy Holliday, Broderick Crawford and William Holden. There was some talk of the female lead being played by Rota Hayworth for a while, but eventually, Holiday, who played the character on stage, agreed to the role.

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4 - Houseboat Cary Grant's third wife wrote the original script for this movie. What is it?
"Three Guys Named Mike"
"Houseboat"
Cary Grant and Sophia Loren starred in "Houseboat" together. Grant's wife Betsy Drake originally wrote it and was meant to star in it until Grant had an affair with Loren and decided to ditch Drake, have the script rewritten and drop her name from it entirely. Then he and Loren broke up.
"How to Marry a Millionaire"
"Sabrina"

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29 - Here Comes the Groom Which of these films featured Bing Crosby as a reporter?
"Pillow Talk"
"Here Comes the Groom"
Starring Bing Crosby and Jane Wyman, "Here Comes the Groom" premiered back in 1951. In 1952, there was a radio broadcast of the movie that shortened the whole thing to about 60 minutes and featured Jane Wyman in the same role.
"The Quiet Man"
"Red as a Rose"

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9 - Roman Holiday Do you know which movie was Audrey Hepburn's first major studio film?
"Always With You"
"Let's Dance"
"Roman Holiday"
"Roman Holiday" featured Gregory Peck opposite Audrey Hepburn, who was playing a princess. Elizabeth Taylor was one of the first choices for the lead and Cary Grant was offered a role as well, but neither one was available to do it, though rumor says Grant turned it down because he felt all the attention would have been on the female role.
"Sunny Side of the Street"

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39 - Happy Go Lovely Which film featured TV's Joker Caesar Romero?
"Pillowtalk"
"High Society"
"Happy Go Lovely"
"Happy Go Lovely" was a British comedy from 1951 starring David Niven and Vera-Ellen. It also featured Caesar Romero, who would achieve the ultimate degree of kitschy fame as the Joker on "Batman" with Adam West in the '60s.
"The Wrong Sister"

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25 - Ain't Misbehavin Do you know which of these movies is about an uncultured young woman making a splash in high society?
"Ain't Misbehavin'"
"Ain't Misbehavin'" featured Piper Laurie, Mamie Van Doren and Rory Calhoun. It's mostly remembered these days for the title song which does get performed in the movie and has managed to outlive the film itself.
"Forever, Darling"
"White Knight"
"The First Dance"

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34 - It Should Happen to You This movie featured Jack Lemmon's first major role. What was it?
"It Should Happen to You"
Jack Lemmon was asked to change to his name before appearing in "It Should Happen to You" because studio bosses thought the press would pan the movie and call it a lemon, playing off the actor's name. Lemmon declined.
"Key to the City"
"It's Always Fair Weather"
"Beloved Liar"

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30 - The Matchmaker Which movie featured "Psycho" star Anthony Perkins?
"The Seven Year Itch"
"The Matchmaker"
Shirley Booth, Anthony Perkins, and Shirley Maclaine starred in "The Matchmaker" a 1958 rom-com. The somewhat more well-known musical "Hello, Doly!" is based on the same play originally.
"Wagon's East"
"Breaking Glass"

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32 - Designing Woman Which 1957 film won the Academy Award for Best Screenplay?
"Some Like it Hot"
"Designing Woman"
Lauren Bacall and Gregory Peck starred in "Designing Woman." Bacall filmed the movie while her husband Humphrey Bogart was in the end stages of cancer. She took the role to distract herself from what was happening.
"Our Girl Friday"
"Born to be Loved"

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38 - Phffft Despite being a rom-com, this movie starts with a divorce. What is it?
"Indiscreet"
"Phffft"
Aside from having a delightful name, "Phfft" featured Jack Lemmon and Judy Holiday as a couple who divorce and then fall in love and remarry again. It was actually the second movie that year that Holliday and Lemmon made together after "It Should Happen To You."
"Houseboat"
"Our Girl Friday"

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37 - Three Guys Named Mike Which of these movies is about a flight attendant?
"Three Guys Named Mike"
Jane Wyman starred in "Three Guys Named Mike" as an airline stewardess with American Airlines who is also a bit of a bungler and managed to get nearly fired from her job about four or five times over the course of the whole film.
"Pat and Mike"
"The Tender Trap"
"Love's Confusion"

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22 - Our Girl Friday This film was also called "The Adventures of Sadie." Do you know it?
"This is it"
"The Long Night"
"Our Girl Friday"
Joan Collins starred in "Our Girl Friday" as a woman named Sadie who gets stranded on a deserted island with three other people. According to Collins, she was the first woman ever to appear in a movie wearing a bikini thanks to this film.
"Roman Holiday"

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