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.
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.
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 Millionembodies 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 Millionis one ofAudrey 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 caperthat came toward the end of the Old Hollywood era. Within a few years, movies likeHow to Steal a Millionquickly became seen as old-fashioned, but it has still stood the test of time.
Bringing Up Babyis 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 thatBringing Up Babywas Hepburn’s first comedic role.
Cary Grant and Katharine Hepburnmade four movies together in total. IfBringing Up Babyisn’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 attempt to find a missing leopard, dig up a rare dinosaur bone and stay out of prison, all in one day.
TheMarx brothers created some of the funniest comediesduring the Golden Age of Hollywood, andDuck Souphas 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 inDuck Soupthat 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, butGroucho 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, andDuck Soup’s skewering of incompetent, self-serving politicians has never gone out of style.
There’s something strangely modern about the premise ofHarvey, 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 ofJames Stewart’s moviesare more dramatic, Stewart makes the most of his everyman charms inHarvey.It takes a rare talent to make such an unusual character so relatable and likable.
Harveyoften 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 ofHarvey,conformity is a straitjacket more restrictive than any perverse sanatorium or fictional medical treatment.
Singin' in the Rainis the kind of lavish, extravagant musical that rarely gets made these days. Many of thebest movie musicalsof 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 Rainis an ode to Hollywood and the joy of musicals, taking place during the shift from silent movies to “talkies”.
Singin' in the Rainhas 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.
His Girl Fridayis 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 dynamicas 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 Fridayends 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.
The Generalis one ofBuster 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 Generalis 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, butThe Generalis creative enough to retain most of its charms. It was initially deemed a flop, but it has grown in stature over the years.The Generalhas entered the public domain, so it can be watched for free online.
Billy Wilder was an extremely versatile director, but he produced a lot of his best work in the comedy genre.Some Like It Hotwas his second collaboration with Marilyn Monroe, after 1955’sThe 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 Hotfollows 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 ofTootsieorMrs. 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 Hothas a great script, ending with one of the great punchlines in cinema.
Peter Sellers delivers one of the greatest comedic performances of all time inDr. 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 turnDr. Strangeloveinto a risible personal satire, with each nation’s foibles ultimately contributing to the end of the world.
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Dr. Strangeloveis one ofStanley Kubrick’s best movies, and definitely his funniest. He wasn’t known as a comedy director, butDr. Strangeloveshows 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. Strangelovehas a lot to say about politics that takes place behind closed doors.
Arsenic and Old Lacesees 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 Laceis surprisingly macabre for such an old comedy.
Arsenic and Old Lacestarted 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.
