The 1950s were a highly-influential and significant period in Hollywood that introduced audiences to some truly iconic and enduring comedy greats. The decade was a booming time for the cinema and entertainment industry, as studios were adamant in attracting viewers to theaters after television took the world by storm. The comedy genre also saw a resurgence in popularity, as revered directors like Billy Wilder, Howard Hawks, and Alexander Mackendrick helmed beloved pictures that continue delivering laughs to this day.

Update July 19, 2023: This article has been updated with even more great comedies from the 1950s that you will love.

Some of Tinseltown’s most dazzling and dynamic stars headlined these projects, with legendary performers such as Jack Lemmon, Spencer Tracy, Marilyn Monroe, and Audrey Hepburn showcasing their comedic chops in the flicks. Gene Kelly and Debbie Reynolds danced their way across the silver screen in the critically-lauded musical romantic comedy Singin’ in the Rain, while pop culture history was made when Monroe donned her iconic white dress and stood over a subway grate in the adored Wilder comedy The Seven Year Itch. Let’s take a look at some of the best classic comedy movies of the 1950s.

14 Some Like It Hot (1959)

Some Like It Hot
United Artists 

Hollywood legends Marilyn Monroe, Tony Curtis, and Jack Lemmon teamed up to star in the uproarious 1959 romantic comedy Some Like It Hot, which follows two male musicians in 1929 Chicago who witness a Mafia murder and seek refuge within an all-female jazz band in which they disguise themselves as women.

Related: These Are the Best Marilyn Monroe Movies

The cheeky picture was directed by revered filmmaker Billy Wilder and premiered to both critical and commercial success, with its massive popularity being the primary factor in the replacement of the Hays Code; Some Like it Hot's LGBTQ+ themes and inclusion of cross-dressing openly defied the controversial censorship. Some Like It Hot is widely regarded as one of the greatest films of all time and is a knockout comedy classic.

13 An American in Paris (1951)

An American in Paris
Loew's Inc. Entertainment

Gene Kelly starred in the captivating 1951 musical romantic-comedy An American in Paris, telling the story of a gifted but struggling painter who, after serving in World War II, decides to stay in France and try to establish a career for himself, only to find his personal life in chaos after falling for the same beautiful French girl as his best friend and fellow veteran.

The Vincent Minnelli picture premiered to universal acclaim upon its release, winning six Academy Awards including Best Picture, and taking the world by storm with its memorable renditions of classic songs like "Love Is Here to Stay" and "'S Wonderful." The iconic climax of the breathtaking film featured lead stars Kelly and Leslie Caron sharing a spectacular 14-minute dance duet to the titular tune, a ballet sequence that cost nearly half a million dollars to create. An American in Paris remains one of the most beloved musicals of all time.

12 Roman Holiday (1953)

Gregory Peck and Audrey Hepburn in Edith Head's costumes for Roman Holiday
Paramount Pictures

Cinema icons Audrey Hepburn and Gregory Peck portray star-crossed lovers in the Oscar-winning 1953 romantic comedy Roman Holiday, with the adored flick centering on frustrated European princess Ann as she embraces a day full of freedom in Rome with the charming American reporter Joe Bradley.

The beloved Hepburn staple was the actress’ first major role and led to her becoming a household name and a highly sought after performer, with director William Wyler having commented, “She had everything I was looking for: charm, innocence, and talent. She also was very funny. She was absolutely enchanting, and we said, 'That's the girl!’” Roman Holiday earned Hepburn the Academy Award for Best Actress and was lauded for its playful humor and brilliant chemistry between the two talented leads.

11 The Ladykillers (1955)

The Ladykillers
The Rank Organisation 

Alexander Mackendrick directed the 1955 British dark comedy crime film The Ladykillers, telling the entertaining story of five eccentric thieves who band together in order to execute a bank heist, renting rooms from a hilariously suspicious elderly lady to concoct their plan. It doesn’t take long until the inept crooks believe they must eliminate the old woman, causing the criminals to develop a mistrust of one another that naturally leads to murder and mayhem.

William Rose wrote the screenplay for the quirky comedy, having allegedly dreamt the whole premise and subsequently captured his oddball idea on paper. The Ladykillers featured wonderfully outlandish performances by stars like Alec Guinness and Peter Sellers and has since been adapted countless times in film, radio, and on stage. The film was so beloved by the great Coen brothers that they created a direct remake with Tom Hanks, though the original is the masterpiece.

10 It Should Happen to You (1954)

It Should Happen to You
Columbia Pictures 

The delightful Jack Lemmon first displayed his leading man capabilities when he starred in the 1954 romantic comedy It Should Happen to You, appearing alongside Judy Holliday and Peter Lawford in his first major film role. The playful picture centers on the fame-hungry Gladys Glover, who finds her ultimate wish granted when she catches the eye of a successful filmmaker after investing in a billboard to gain attention, also attracting the affections of a notorious playboy. Upon its release, It Should Happen to You garnered rave reviews for its dynamite performances and infectious humor, with The New York Times calling it, “a neat piece of comic contrivance that will contribute to the joy of man” with “intelligence, compassion, and lots of gags.”

9 The Seven Year Itch (1955)

Marilyn Monroe in a white dress in The Seven Year Itch
20th Century Fox

Famous for containing one of the 20th century’s most iconic pop-culture images ever captured, Billy Wilder’s 1955 romantic comedy The Seven Year Itch notoriously featured Marilyn Monroe as the object of a middle-aged New Yorker’s fantasy when he is left alone by his wife for the summer. Tom Ewell starred opposite the blonde bombshell in the instantly recognizable flick, as his character finds himself completely enamored by his stunning next-door-neighbor that naturally leads to sidesplitting hijinks. The scene in which Monroe wore a white dress and stood above a windy subway grate helped cement the comedy’s place in cinema history, as did the actress’ spirited chemistry and playful banter with her co-star Ewell.

8 High Society (1956)

Elegantly dressed Kelly between two tuxedoed men in High Society
Metro-Goldwyn-Mayer

Tinseltown's brightest stars Grace Kelly, Frank Sinatra, and Bing Crosby headlined the Oscar-nominated 1956 musical romantic comedy High Society, a remake of the celebrated '40s hit The Philadelphia Story that follows the efforts of respected jazz musician C.K. Dexter-Haven (Crosby) as he attempts to woo his socialite ex-wife Tracy after learning of her upcoming nuptials to another man. The already messy situation grows more complicated when a tabloid reporter (Sinatra) covering the wedding also falls for the beautiful Tracy, as the potential suitors set out to capture the young woman's heart.

High Society truly thrives off the undeniable chemistry between its three phenomenal leads, with Sinatra and Crosby showcasing their incredible vocals with performances of songs like "True Love" and "You're Sensational." The rom-com was a huge hit with audiences and critics, becoming one of the highest grossing releases of the year; it was also Kelly's final role before she became Princess of Monaco.

7 Father of the Bride (1950)

Father of the Bride
Loew's, Inc. 

Spencer Tracy and Elizabeth Taylor appeared as the eponymous characters in the 1950 comedy Father of the Bride, which follows doting dad Stan as he is forced to confront his feelings regarding the impending nuptials of his beloved daughter Kay in addition to the stress of planning a wedding.

The comical picture shines in large part because of Tracy’s wonderfully balanced portrayal of the anxious father, with the famed actor delivering both tender and laughable moments as the big day grows nearer; Tracy was nominated for an Academy Award for his performance, and its success led to the 1951 follow-up Father’s Little Dividend. Father of the Bride was remade multiple times, most notably with Steve Martin in 1991 and in 2022 with Andy García.

6 Abbott and Costello Meet the Mummy (1955)

Abbott and Costello in  Meet the Mummy
Universal-International 

Legendary comedy dream team Abbott and Costello were revered for their sidesplitting routines and performances, with the duo once again charming audiences when they starred in the 1955 classic horror comedy Abbott and Costello Meet the Mummy. In the amusing farce, the funnymen appear as two gauche Americans stranded in Egypt who stumble upon a sacred medallion that leads them to the crypt of the titular mummy Klaris.

Related: How Abbott and Costello Helped Create the Horror Comedy

The film marked one of the final collaborations between the comedians, whose show business partnership ended in 1957 after they headlined their final project together Dance with Me, Henry due to their waning popularity and shift in audience’s taste in comedy. Still, their excellent reign of comedy movies (especially the horror comedy goldmine of this and Abbot and Costello Meet Frankenstein, from 1948) has left a treasure trove of classics to dive back into over the years.

5 Pillow Talk (1959)

Pillow Talk
Arwin Productions

Rock Hudson and Doris Day shined as enemies-turned-lovers in the 1959 romantic comedy Pillow Talk, which follows the ultimate ladies man and successful songwriter Brad Allen as he engages in a slew of short-lived romances that irritate his interior decorator neighbor Jan, who shares the same telephone line as him and has never met in person. After Brad spots Jan at a party (unaware that they are neighbors), he sets out to romance the woman by adopting a larger-than-life alter ego, resulting in hilarious hijinks.

Co-starring Tony Randall as Brad's best friend, who also falls in love with Jan, the playful picture marked the first of three romantic comedies featuring the sensational stars and was lauded as one of the biggest hits of the year. Pillow Talk took home the Academy Award for Best Screenplay and also helped revive Hudson's waning career, showcasing his versatility as an actor and ability to branch out of dramas into the comedy genre.

4 Gentlemen Prefer Blondes (1953)

Marilyn Monroe in gentlemen prefer blondes
20th Century Fox

Marilyn Monroe and Jane Russell were an unstoppable dynamic duo in Howard Hawks' 1953 musical comedy Gentlemen Prefer Blondes, in which the lovely ladies portray American showgirls who take a luxurious cruise on their journey to Paris, where the gold-digging Lorelei Lee sets her sights on a wealthy, smitten old man and Dorothy Shaw becomes enamored by the handsome private detective secretly investigating her best friend.

Monroe's iconic performance of the song "Diamonds Are a Girl's Best Friend" and her satin pink dress have become synonymous with the engrossing picture, as were the Hollywood greats' endearing chemistry and witty humor. Gentlemen Prefer Blondes has also been retrospectively praised for its trailblazing depiction of female friendship, as Lorelei and Dorothy remain completely loyal and devoted to one another despite their conflicting temperaments and desires; the comedy has since been celebrated as a sharp and playful satire.

3 Singin' in the Rain (1952)

Gene Kelly in Singin in the Rain
Metro-Goldwyn-Mayer

Cinema greats Gene Kelly, Debbie Reynolds, and Donald O’Connor headlined the beloved 1952 musical romantic comedy Singin’ in the Rain, a dazzling picture that is widely regarded as the greatest musical film ever created. The charming comedy depicts Tinseltown in the 1920s, centering on silent movie star Don Lockwood as he attempts to transition to talkies while falling for the spirited chorus girl Kathy Selden.

Singin’ in the Rain is revered for its iconic musical numbers, including the titular tune, “Make ‘Em Laugh” and “All I Do Is Dream of You”, as well as it's spectacular cinematography and good-natured humor. The toe-tapping film is considered one of the greatest classic Hollywood movies as a result and has been lauded by audiences and critics alike, currently holding a perfect score on Rotten Tomatoes.

2 Gigi (1958)

Gigi 1958

Based on the Colette novella of the same name, the 1958 musical romantic comedy Gigi stars Leslie Caron in the eponymous role, in which the actress brilliantly portrays the carefree and precocious character who attempts to master the ways of high Parisian society while enjoying a spirited friendship with uneasy playboy Gaston (Louis Jourdan). Despite attempting to keep one another at arm's length, the duo begin to develop romantic feelings for one another, though Gigi refuses to settle for anything less than being someone's wife and not mistress.

Gigi won all nine of its Academy Award nominations including Best Motion Picture, and was revered for its stunning visuals, spirited performances, and delightful musical numbers. In their glowing review of the romantic comedy at the time, the Chicago Tribune declared, "Charm is a much abused word, but it is that elusive quality which marks this smooth, sophisticated musical from start to finish."

1 Monkey Business (1952)

Monkey Business
20th Century Fox

Howard Hawks directed the 1952 black and white screwball comedy Monkey Business, enlisting Hollywood greats like Cary Grant, Ginger Rogers and Marilyn Monroe to help tell the zany story of brilliant research chemist Dr. Barnaby Fulton who finds his life completely disrupted when a chimpanzee from one of his experiments discovers the fountain of youth. It doesn’t take long until Fulton decides to test out the elixir himself, resulting in the good doctor to act like a teenager and run around town causing comical chaos. Monkey Business is a screwball classic that really showed off Grant’s willingness to be goofy and embrace a more over-the-top role, and film critic John Belton called the uproarious picture Hawks’ “most organic comedy.”