Comedy generally doesn’t age as well as most other genres, but there are still some timeless classics from the Old Hollywood era that can make modern audiences laugh in the 21st century. Many of these older comedies have been recognized as some of the funniest movies of all time, since they have stood the test of time and entertained people for decades, and they’re still funnier than the majority of new comedies.
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Comedy requires a mutual understanding, so older movies often have dated references that lose their relevance over time. What can be even worse is if an older comedy has some topics that are seen in a poor light by modern standards. Changing social attitudes mean that people’s senses of humor also change over time. Only the funniest and most universal Old Hollywood comedies manage to be just as popular these days.
You are watching: 10 Old Hollywood Comedies That Are Still Hilarious
10
How To Steal A Million (1966)
Audrey Hepburn Embodies ’60s Chic In William Wyler’s Heist Comedy
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How to Steal a Million
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Release Date
August 19, 1966
Director
William Wyler
Cast
Audrey Hepburn
, Peter O’Toole
, Eli Wallach
, Hugh Griffith
, Charles Boyer
, Fernand Gravey
, Marcel Dalio
, Jacques Marin
The heist genre had a renaissance in the 1960s, with a new generation of stories which added more comedy and romance than the classics of the film noir era. How to Steal a Million embodies this trend. It’s a breezy and intelligent romcom that incorporates some crime to add an edge to the story. Audrey Hepburn plays the daughter of an art forger who has to steal one of her father’s paintings from a gallery before the fraud is discovered.
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How to Steal a Million is one of Audrey Hepburn’s best movies, thanks to her affable performance, her chemistry with Peter O’Toole, and her iconic wardrobe provided by Givenchy. It’s a gloriously stylish crime caper that came toward the end of the Old Hollywood era. Within a few years, movies like How to Steal a Million quickly became seen as old-fashioned, but it has still stood the test of time.
9
Bringing Up Baby (1938)
Bringing Up Baby Is A Fast-Paced Treat
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Bringing Up Baby
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Release Date
February 18, 1938
Director
Howard Hawks
Cast
Katharine Hepburn
, Cary Grant
, Walter Catlett
, Barry Fitzgerald
Bringing Up Baby is a defining work of the screwball comedy genre, which satirizes the romance genre with farcical situations and the challenging of traditional gender roles. Cary Grant plays an awkward, anxious paleontologist, while Katharine Hepburn plays the zany, manic socialite who manages to sweep him up in her ludicrous world. It’s hard to believe that Bringing Up Baby was Hepburn’s first comedic role.
Cary Grant and Katharine Hepburn made four movies together in total. If Bringing Up Baby isn’t the best, it’s easily the funniest. The rapid dialogue packs in a dizzying number of jokes, but there’s also a lot of humor taken from the very fact that everything is unfolding without any room to take a break. Grant and Hepburn feed off of each other’s energy as they try to find a missing leopard, dig up a rare dinosaur bone and stay out of prison, all in one day.
8
Duck Soup (1933)
Duck Soup’s Political Farce Is Still Sadly Relevant
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Duck Soup
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Release Date
November 17, 1933
Director
Leo McCarey
Cast
Groucho Marx
, Harpo Marx
, Chico Marx
, Zeppo Marx
, Margaret Dumont
, Louis Calhern
, Edmund Breese
The Marx brothers created some of the funniest comedies during the Golden Age of Hollywood, and Duck Soup has emerged as the one which has remained the most popular in the decades since. The movie takes place in the fictional republic of Freedonia, as Groucho’s Rufus T. Firefly storms to power as the inept and offensive ruler. Firefly’s abrasive personality soon sends the country spiraling into a war with neighboring Sylvania.
The jokes come so thick and fast in Duck Soup that it hardly matters when one of them doesn’t land, since there are three or four more piled on immediately afterward. Each of the four stars gets a chance to shine, but Groucho is often the focus. His mirror scene is a joy to watch, and he pairs this physical comedy with a barrage of one-liners. The chaotic war scene is the height of political farce, and Duck Soup‘s skewering of incompetent, self-serving politicians has never gone out of style.
7
Harvey (1950)
James Stewart Turns On The Charm
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Harvey
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Release Date
December 21, 1950
Cast
James Stewart
, Josephine Hull
, Peggy Dow
, Charles Drake
, Cecil Kellaway
, Victoria Horne
, Jesse White
, William H. Lynn
, Wallace Ford
, Nana Bryant
, Grayce Mills
, Clem Bevans
Director
Henry Koster
There’s something strangely modern about the premise of Harvey, a movie about a man whose best friend is a giant invisible rabbit, but it’s a sweet and endearing movie seeped in the magic of Old Hollywood. While many of James Stewart’s movies are more dramatic, Stewart makes the most of his everyman charms in Harvey. It takes a rare talent to make such an unusual character so relatable and likable.
Harvey often resembles a comedy of errors, but it mixes its humor with some deeply meditative human drama. Ultimately, it’s easy to be won over by Elwood P. Dowd’s large rabbit friend, whether he’s real or not. A lot of the comedy works so well because it works to reinforce the story’s sentimental core. In the world of Harvey, conformity is a straitjacket more restrictive than any perverse sanatorium or fictional medical treatment.
6
Singin’ In The Rain (1952)
Gene Kelly’s Musical Represents Something That Modern Hollywood Lacks
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Singin’ in the Rain
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Release Date
April 11, 1952
Director
Stanley Donen
, Gene Kelly
Cast
Gene Kelly
, Donald O’Connor
, Debbie Reynolds
, Jean Hagen
, Millard Mitchell
, Cyd Charisse
Singin’ in the Rain is the kind of lavish, extravagant musical that rarely gets made these days. Many of the best movie musicals of all time were produced in the 1950s and 1960s, and there’s something about the gorgeous style of that era that has never been replicated. Singin’ in the Rain is an ode to Hollywood and the joy of musicals, taking place during the shift from silent movies to “talkies”.
Singin’ in the Rain has plenty of ways of making its audience laugh, including its charming romantic humor and plenty of sharp dialogue. Some of the joyous musical numbers are also hilarious, especially Donald O’Connor’s energetic one-man show, “Make ‘Em Laugh,” in which he literally bounces off the walls, runs in circles and almost beats himself senseless to entertain his audience.
5
His Girl Friday (1940)
Howard Hawks’ Romantic Satire Is Still Worth Watching
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His Girl Friday
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Release Date
January 18, 1940
Director
Howard Hawks
Cast
Cary Grant
, Rosalind Russell
, Ralph Bellamy
, Gene Lockhart
His Girl Friday is a screwball comedy that mocks the confines of traditional gender roles, as a woman is torn between her career as a newspaper reporter and a potential life of domesticity with her new fiancé. Rosalind Russell and Cary Grant strike up a hilarious dynamic as two fast-talking, career-oriented people who need more of a human touch. This is a fun subversion of other romcoms that feature one career-driven individual who meets a romantic partner who shows them that there’s more to life.
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Predictably, His Girl Friday ends with the two bickering partners getting back together, but it hardly seems like a happy ending. In keeping with the movie’s skeptical view of marriage and domesticity, their reunion seems doomed to fail in the exact same way as their first relationship. His Girl Friday‘s ending is just one element of its smart romantic satire, and a lot of its social commentary is still relevant today.
4
The General (1926)
Buster Keaton’s Stunts Are Constantly Creative
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The General
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Release Date
December 25, 1926
Director
Buster Keaton
Cast
Buster Keaton
, Marion Mack
, Glen Cavender
, Jim Farley
, Frederick Vroom
, Frank Barnes
, Charles Henry Smith
, Joe Keaton
, Mike Donlin
, Tom Nawn
, Jimmy Bryant
, Budd Fine
, Eddie Foster
, Frank Hagney
, Ray Hanford
, Jack Hanlon
, Edward Hearn
, Hilliard Karr
, Elgin Lessley
, Louis Lewyn
, Jackie Lowe
, Charles Phillips
, Al St. John
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The General is one of Buster Keaton’s best movies, and it showcases his talents as a legendary physical comedian. Keaton’s stunts have to be seen to be believed. He’s constantly willing to put his body on the line to get a laugh, and there’s a simple joy to witnessing him pull off the impossible with remarkable regularity. He’s the closest that Hollywood has come to producing a real-life cartoon character.
The General is based on a true story that took place during the American Civil War, with Keaton playing a train conductor who gets caught up in a cross-country chase on the railroads. There aren’t many silent era movies which still pack a punch, but The General is creative enough to retain most of its charms. It was initially deemed a flop, but it has grown in stature over the years. The General has entered the public domain, so it can be watched for free online.
3
Some Like It Hot (1959)
Billy Wilder And Marilyn Monroe Rekindle Their Winning Partnership
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Some Like It Hot
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Release Date
March 15, 1959
Director
Billy Wilder
Cast
Marilyn Monroe
, Tony Curtis
, Jack Lemmon
, George Raft
, Pat O’Brien
, Joe E. Brown
Billy Wilder was an extremely versatile director, but he produced a lot of his best work in the comedy genre. Some Like It Hot was his second collaboration with Marilyn Monroe, after 1955’s The Seven Year Itch, and, once again, he gets the best out of her talents and her glamorous allure. Monroe is joined by Tony Curtis and Jack Lemmon, two of the funniest actors of their time.
Some Like It Hot follows two musicians who disguise themselves as women to escape the Chicago mob without being detected. Its quirky gender commentary will probably appeal to any fans of Tootsie or Mrs. Doubtfire, and it also has the same hilarious dramatic irony of these movies, as the two musicians desperately try to keep their ruse alive. Some Like It Hot has a great script, ending with one of the great punchlines in cinema.
2
Dr. Strangelove (1964)
The Cold War Satire Has Aged Beautifully
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Dr. Strangelove Or: How I Learned To Stop Worrying And Love The Bomb
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Release Date
January 29, 1964
Director
Stanley Kubrick
Cast
George C. Scott
, Slim Pickens
, Peter Sellers
, Keenan Wynn
, Sterling Hayden
Peter Sellers delivers one of the greatest comedic performances of all time in Dr. Strangelove, Stanley Kubrick’s timeless political satire. Sellers plays three characters from three different countries: the US president, a British military man and an unhinged German scientist. Sellers’ mannerisms turn Dr. Strangelove into a risible personal satire, with each nation’s foibles ultimately contributing to the end of the world.
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Dr. Strangelove is one of Stanley Kubrick’s best movies, and definitely his funniest. He wasn’t known as a comedy director, but Dr. Strangelove shows that he can subtly embellish a hilarious script with some thoughtful visual touches. Kubrick also focuses a lot on the shifting power dynamics at play, showing how the personal reflects the global. Although it’s now decades away from its original Cold War context, Dr. Strangelove has a lot to say about politics that takes place behind closed doors.
1
Arsenic & Old Lace (1944)
Frank Capra’s Dark Comedy Is Unlike Most Other Old Hoolywood Movies
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Arsenic and Old Lace
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Release Date
September 1, 1944
Director
Frank Capra
Cast
Cary Grant
, Priscilla Lane
, Josephine Hull
, Jean Adair
, Raymond Massey
, John Alexander
, Peter Lorre
, Jack Carson
, Edward Everett Horton
, James Gleason
, Grant Mitchell
, Edward McNamara
, Garry Owen
, John Ridgely
, Vaughan Glaser
, Chester Clute
, Charles Lane
, Edward McWade
, Hank Mann
, Spencer Charters
, Sol Gorss
, Lee Phelps
, Raymond Walburn
, Spec O’Donnell
, Leo White
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Arsenic and Old Lace sees Cary Grant on top form, playing the only sane member of a family rife with unhinged serial killers. It’s a raucous dark comedy that still holds up, even if the idea of a man who constantly reenacts the Battle of San Juan is even more outdated than it was in 1944. Aside from this reference, Arsenic and Old Lace is surprisingly macabre for such an old comedy.
Arsenic and Old Lace started life as a Broadway play, but Frank Capra felt compelled to adapt it for the big screen. The movie’s theatrical origins can be seen in the limited setting, but Capra also seems to bring the types of broad performances out of his actors that usually read well on stage. Each of Grant’s cartoonish overreactions fit the tone of the dark comedy perfectly. He adds a sliver of sanity to a bizarre family unit.
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