10 Most Timeless Classic Comedy Movies, Ranked

Among all film genres, comedy stands as one of the most unifying and influential, having entertained audiences since the early days of cinema. During the 1930s, the majority of American audiences turned to classic comedies such as It Happened One Night, Bringing Up Baby, and A Night at the Opera as a way to escape from their immense hardships and struggles brought on by the infamous stock market crash. As the demand for comedies grew, so did the genre, evolving into screwball comedies, slapstick, and satire, which serve as the foundation of the genre today.

Even as comedy evolves and adapts to entertain modern audiences today, there’s still something to be said about classic comedies such as His Girl Friday starring Cary Grant and Rosalind Russell, Singin’ in the Rain, and Mel Brooks‘ Blazing Saddles, which many film fans consider to be timeless contributions to the comedy genre. From the 1968 comedy hit The Odd Couple to Billy Wilder‘s Some Like It Hot, these are the ten most timeless classic comedy movies, ranked!

10

‘The Odd Couple’ (1968)

Directed by Gene Saks

The Odd Couple is a chaotic comedy based on the 1965 stage production written by Neil Simon, starring Jack Lemmon and Walter Matthau, who worked together on several hit comedies throughout their careers. Set in New York City, the movie follows Felix Unger (Lemmon), who, after recently separating from his wife, agrees to move in with his friend and sportswriter, Oscar Madison (Matthau). Despite having a solid friendship, Felix’s perfectionist behavior and Oscar’s messy and carefree lifestyle mix as well as oil and water, resulting in a haywire living arrangement for the two friends.

The Odd Couple showcases the uncanny chemistry between Lemmon and Matthau, who are easily one of the most underappreciated comedic duos in movie history. While they still leave audiences in stitches, Lemmon and Matthau convey a certain sentimental depth and vulnerability that ultimately makes The Odd Couple a timeless comedy classic. The movie was a general success and went on to earn two Oscar nominations for Best Screenplay and Best Film Editing. In 1970, the movie inspired a popular sitcom of the same name starring Tony Randall and Jack Klugman, which ran for five seasons.

9

‘Singin’ in the Rain’ (1952)

Directed by Gene Kelly and Stanley Donen

Gene Kelly stars in the classic musical comedy Singin’ in the Rain as a silent film star, Don Lockwood, who convinces the studio to turn his upcoming movie into a musical production to compete with the arrival of the talkies. Unfortunately, Lockwood’s frequent co-star, Lina Lamont (Jean Hagen), has a less-than-desirable voice, but when Lockwood meets a young aspiring actress, Kathy Seldon (Debbie Reynolds), she agrees to dub Lamont’s voice in exchange for a film contract.

Singin’ in the Rain is a lighthearted satire of Hollywood that not only covers the cutthroat way of show business but also a pivotal moment in movie history with a cheeky sense of humor. Initially, the movie was a moderate hit, but through the years, it has been cited as one of the greatest musical movies of all time and a favorite among classic film fans. While some may not be fans of the musical genre, Singin’ in the Rain is one of the few exceptions that has something for every kind of movie lover, such as romance, drama, and slapstick humor, making it a well-balanced classic comedy.

8

‘Bringing Up Baby’ (1938)

Directed by Howard Hawks

Cary Grant stars in Howard Hawks‘ Bringing Up Baby as a straitlaced paleontologist, David Huxley, who is anxious to make a good impression on a wealthy woman, Mrs. Random (May Robson), who is considering making a large donation to Huxley’s museum. On the day before his wedding, Huxley has a chance encounter with Random’s adventurous niece, Susan Vance (Katharine Hepburn), and soon finds himself in a series of chaotic predicaments brought on by the young heiress and a pet leopard named Baby.

Bringing Up Baby is an essential screwball comedy that, despite not performing well at the box office, fared well with the majority of critics, who commended the film’s zany premise, Hawks’ spontaneous direction, and sidesplitting performances by both Grant and Hepburn. With Grant’s zealously unpredictable comedic style and Hepburn’s spot-on low comedy, the stars make a humorous pair and are the epitome of the classic straight man and funny man comedy duo. Today, Bringing Up Baby is recognized as a first-rate screwball comedy classic, and while some may be put off by the black-and-white format, it’s without question one of the most timeless classic comedies.

7

‘Monty Python and the Holy Grail’ (1975)

Directed by Terry Gilliam and Terry Jones

Monty Python and the Holy Grail is a clever comedy that parodies the legend of King Arthur and his search for the Holy Grail, starring members of the iconic British comedy troupe, Monty Python, which consists of John Cleese, Eric Idle, Graham Chapman, Terry Gilliam, Terry Jones, and Michael Palin. The movie leads audiences on a hilarious quest that showcases the group’s signature style of unpredictable humor and random but effective gags, making Monty Python and the Holy Grail one of the most timeless entries in modern comedy.

Despite its initial mixed reviews, Monty Python and the Holy Grail grossed more than any other British film in 1975, and today, it is widely considered to be one of the best comedies of all time, noted for its uninhibited humor, memorable jokes, and performances that never fail to leave audiences in stitches. Between the film’s originality and Monty Python’s ingenious craft and daring talent, the film is, without question, a genuine article of comedy gold. Like every type of comedy, Monty Python and the Holy Grail is a bit of an acquired taste, but whether one is a fan or not, it doesn’t diminish the film’s monumental influence and significant legacy in the world of comedy.

6

‘His Girl Friday’ (1940)

Directed by Howard Hawks

Grant reunited with Hawks to star in the director’s groundbreaking screwball comedy, His Girl Friday, which is based on the 1928 play, The Front Page, written by Ben Hecht and Charles MacArthur. The movie centers around an all-star reporter, Hildy Johnson (Rosalind Russell), who has decided to retire from her job and settle down with her soon-to-be husband (Ralph Bellamy). When Johnson tells her editor and ex-husband, Walter Burns, about her plans, he makes a deal with her to take on one more story before tying the knot, secretly hoping that the excitement and adrenaline of the job will change her mind.

His Girl Friday is the classic battle of the sexes screwball comedy and one of the first movies to feature overlapping and rapid dialogue, making it one of the fastest talking movies in cinema history. Unlike most directors at the time, Hawks encouraged the cast to be spontaneous and improvise, which, despite causing production delays, turned out to be the key to the film’s massive success. While the entire cast is sensational, Grant truly shines in His Girl Friday as he seemingly improvised his entire performance, coming up with some of the movie’s funniest lines and surprises that still manage to win over laughs from audiences today.

His Girl Friday

Release Date

January 18, 1940

Runtime

92 minutes

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  Rosalind Russell

  Hildy Johnson

5

‘It Happened One Night’ (1934)

Directed by Frank Capra

It Happened One Night is one of the best screwball comedies of all time and stars Clark Gable as an ambitious reporter, Peter Warne, who crosses paths with a young rebellious socialite, Ellie Andrews (Claudette Colbert), who recently made headlines with her surprising marriage to a reputable cad and is trying to get back to him after being shipped off by her disapproving father. Warne strikes a deal with Andrews and agrees to help her reunite with her husband in exchange for an exclusive story, but as they travel to their destination, romantic sparks begin to fly between them.

Frank Capra‘s It Happened One Night is the epitome of a timeless romantic comedy that not only put Columbia Pictures on the map but also made Oscar history by becoming the first film to win in all five major award categories. Gable and Colbert have an undeniable energy and magnetic connection together that serves as the film’s main attraction, luring audiences into a modern fairytale of how opposites indeed attract. It Happened One Night was a smash at the box office and, aside from a few mixed reviews, received glowing reviews from critics, who commended the film’s vibrant dialogue, Capra’s fearless direction, and charming comedic performances by both Gable and Colbert.

4

‘A Night at the Opera’ (1935)

Directed by Sam Wood

The Marx Brothers were a crucial force in shaping comedy for the silver screen, and while they appeared together in several successful classics, their first movie with MGM Studios, A Night at the Opera, stands to be not only one of their best but also a timeless essential comedy. Groucho Marx stars as a sly business manager, Otis B. Driftwood, who, along with his friends, Fiorello (Chico Marx) and Tomasso (Harpo Marx), take the world of opera by storm as they help two Italian opera singers find success on the American stage, ultimately winning the day and humiliating their uptight opponents in the process.

A Night at the Opera is a bona fide laugh fest full of sharp slapstick comedy and ridiculous gags that only the Marx Brothers could pull off with such maniacal delight. Compared to their films with Paramount Pictures, A Night at the Opera has a more sophisticated tone that aligns with MGM’s posh reputation, but to the Marx Brothers’ credit, they still manage to override the mismatching vibe with their distinct blend of comedy and gimmicks. The movie went on to become MGM’s highest-grossing film of the year, and even though some may argue that the film fails to live up to their early work, A Night at the Opera still features their original shtick of poking fun at the stuffy and sophisticated crowd, but with a heavy focus on satirical puns and comedic anarchy.

A Night at the Opera

Release Date

November 15, 1935

Runtime

96 Minutes

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  Groucho Marx

  Otis B. Driftwood

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3

‘Blazing Saddles’ (1974)

Directed by Mel Brooks

Cleavon Little stars in Mel Brooks’ satirical dark comedy Western Blazing Saddles as a railroad worker, Bart, who becomes the first African-American sheriff in the town of Rock Ridge. Unbeknownst to Bart, he’s a pawn in the government’s plan to drive the racially biased people out of town to expand the new railway, hoping his unexpected arrival will be enough to send them packing. Once Bart discovers the true nature of his recent promotion, he decides to help save the town, and with the help of a rummy gunfighter, Jim (Gene Wilder), convinces the townspeople to band together with him.

Blazing Saddles spares no one with its uncensored humor and stereotypical jokes, which is what ultimately makes it such a wild, timeless comedy. Little and Wilder are a match made in comedy heaven, who brilliantly play off one another with their quick-witted banter and below-the-belt one-liners that go hand in hand with the film’s candid tone. Despite its initial mixed reception from critics, Blazing Saddles earned three Oscar nominations and was an overall hit with audiences. Like all of Brooks’ work, the movie was never intended to be a polished piece of entertainment but instead was designed to entertain audiences with non-stop laughter, which Brooks never fails to achieve.

2

‘Dr. Strangelove’ (1964)

Directed by Stanley Kubrick

Stanley Kubrick‘s Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb is a unique parody of the Cold War that plays off the general societal fears of a nuclear war with a twisted sense of humor. The movie follows an unstable U.S. Air Force general, Jack D. Ripper (Sterling Hayden), who believes that the Soviet Union is poisoning America’s water and orders a preemptive attack on them. When others learn about the unauthorized order, they meet to discuss the next course of action, unaware that their fate, as well as the world’s, has already been sealed.

Out of all of Kubrick’s war movies, Dr. Strangelove is a timeless black political comedy that many film fans and historians consider to be the director’s magnum opus. While the overall cast is phenomenal, Peter Sellers undoubtedly shines the brightest with his eccentric performances as three different characters, ultimately serving as the film’s main source of dark humor and crazed satire. Even though Columbia Pictures was initially less than thrilled about the context of the movie, Dr. Strangelove was both a critical and commercial success and went on to receive several Oscar nominations, including Best Director, Best Picture, and Best Actor for Sellers. Today, Dr. Strangelove is celebrated as one of the greatest comedies of the twenty-first century and a significant classic that continues to incite generations of film fans with uncontrollable laughter.

1

‘Some Like It Hot’ (1959)

Directed by Billy Wilder

Tony Curtis and Jack Lemmon star in Billy Wilder‘s classic romantic comedy, Some Like It Hot, as musicians, Joe and Jerry, who, after witnessing a brutal mob hit, quickly flee Chicago disguised as women in an all-girls band that is headed for sunny Florida. At first, their plan goes off without a hitch, but when Joe falls for a fellow band member (Marilyn Monroe), he juggles his female persona with a wealthy bachelor facade to try and win her over. As if Joe’s womanizing ways weren’t enough trouble, the men realize they have a bigger problem when the gangsters who are looking for them check into their hotel.

Some Like It Hot is one of several movies that led to the end of the Hays Code, and it reigns today as a groundbreaking comedy with its unapologetic sexuality, riveting performances, and unfiltered humor, ultimately making it the most timeless classic comedy. The movie ranked as the third highest-grossing film in the United States during its first week and earned several Oscar nominations, including Best Director, Best Actor for Lemmon, and Best Screenplay, winning for Best Costume Design. Between Wilder’s masterful direction and the excellent cast, which also includes Joe E. Brown and George Raft, Some Like It Hot is an endless riff on gender stereotypes with hysterical punchlines and one-liners that never fail to leave audiences rolling with laughter.

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