There’s a real difference between a movie that makes you smile and one that makes you wheeze with uncontrollable laughter. The first kind is common. The second kind is rare, and when it happens, it tends to stick with you for decades. Comedy doesn’t age well as a general rule. It’s a medium highly dependent upon context, and what’s considered funny now might be met with blank stares years later. So when a movie can still crack audiences up decades or even a century down the line, that’s a sign of a true classic.
Of all the cinematic genres, comedy is the hardest to truly master. Humor is so context-dependent and changes so wildly from person to person that many comedies struggle to have a strong, immediate impact. However, there have been plenty of comedy movies throughout cinematic history that have proven themselves timeless and stand among the best films ever made. The twenty films below represent some of the very best examples of that rare achievement.
1. Some Like It Hot (1959)
Directed by Billy Wilder and released in 1959, “Some Like It Hot” is often regarded as one of the greatest comedies . The film stars Tony Curtis and Jack Lemmon as two male musicians who witness a mob hit and subsequently disguise themselves as women to escape the gangsters, joining an all-female band led by Marilyn Monroe. The narrative blends buddy film, screwball comedy, and gangster parody, showcasing Wilder’s remarkable skill at genre fusion.
The American Film Institute ranked “Some Like It Hot” the single funniest film in cinema history. The film features a tight script with flawless acting and incredible comedic timing. Beyond pure entertainment, it also challenged gender norms, establishing its legacy as an important, iconic, and genuinely hilarious comedy masterpiece. The closing line, delivered by Joe E. Brown, remains one of the most quoted in Hollywood history.
2. Blazing Saddles (1974)
When Mel Brooks released Blazing Saddles, no one had ever seen anything like it, and no one has managed to replicate it since. The film takes the western, one of Hollywood’s most self-serious genres, and blows it apart with comedy. Cleavon Little stars as Bart, a Black sheriff appointed to a racist frontier town, with Gene Wilder playing his alcoholic gunslinger sidekick.
Blazing Saddles is the gold standard for anarchic, rule-breaking comedy. Mel Brooks’s no-holds-barred satire on race and Hollywood conventions was met with both outrage and acclaim, but its impact is undeniable. The poignant humor is of its time and timeless simultaneously, and the film continues to age like fine wine. It firmly places comedy at the forefront of a cultural revolution, allowing laughs to soften the blows of turbulent years.
3. Airplane! (1980)
This iconic spoof of disaster films stars Robert Hays as a former pilot who must overcome his fear of flying to save a plane full of passengers. The film is packed with visual gags, puns, and absurd situations, creating a non-stop comedic experience. Airplane! was one of the first films to establish the spoof genre as a fan favourite, creating a wave of similar comedies in its wake. This massively successful comedy proved to be hugely influential, built on rapid-fire jokes, gags, and deadpan delivery.
Leslie Nielsen’s stern performance is arguably the funniest in cinema history, and the spoof has outlived many of the films it was originally parodying. It remains the finest example of absurdist screwball humor ever put on screen. Audiences continue to discover it with fresh eyes, and the laughs haven’t dimmed one bit.
4. Monty Python and the Holy Grail (1975)
This absurdist comedy from the legendary British troupe, Monty Python, offers a hilarious take on the Arthurian legend. Filled with memorable characters, quotable dialogue, and surreal situations, the film remains a favourite among fans of the group’s unique brand of humor. Its irreverent approach to history and storytelling make it a timeless comedy classic.
Absurdity and surrealism persist throughout, and the film never stops evolving. It’s endlessly quotable and jumps from thoughtful humor to juvenile jokes with relative ease. Monty Python and the Holy Grail never takes its foot off the gas, barreling over the audience with one memorable scene after the other. Few classic comedies put so much into so little, and it arguably has the highest laughs-per-minute of any comedy film ever made.
5. Dr. Strangelove (1964)
The closer the film edges toward annihilation, the funnier it becomes, exposing the insanity of real-world politics. In this regard, the movie was bold for its day and way ahead of the curve in lampooning the doctrine of Mutually Assured Destruction. Stanley Kubrick’s dark masterpiece managed to make the terrifying concept of nuclear war into one of cinema’s most sustained comic achievements.
The American Film Institute placed Dr. Strangelove third on its list of the all-time funniest films. In the end, Dr. Strangelove is proof that the funniest films are often also the smartest. Peter Sellers, playing three distinct roles with effortless precision, delivers a performance that holds up as one of the great comic turns in film history.
6. Annie Hall (1977)
The reason Annie Hall is still loved is because of its wit and fourth-wall-breaking style, but it also redefined how comedy could explore emotion. It is funny, yes, but also brutally self-aware. A love story that refuses to lie about how love often ends. Woody Allen’s semi-autobiographical film changed what audiences expected a romantic comedy to look like.
The film’s script topped the Writers Guild of America’s list of the 101 funniest screenplays ever written, surpassing Some Like It Hot, Groundhog Day, Airplane!, and Tootsie. Diane Keaton’s costume choices in the film created a look that had a genuine influence on the fashion world during the late 1970s, with the style often referred to as the “Annie Hall look.” It’s rare for a comedy to leave that kind of cultural imprint.
7. The Producers (1967)
The beginning of the Brooks empire, and still his funniest film, The Producers combines old-school comedy, Broadway backstage hi-jinks, and outright headline-grabbing bad taste to intoxicating effect. Gene Wilder steals the show as the accountant to Zero Mostel’s portly, conniving stage producer. The central con, an elaborate plan to abscond with the takings of a show so dreadful it closes overnight, keeps things ticking along at a brisk pace.
According to Rotten Tomatoes critics, The Producers is one of Mel Brooks’s finest as well as funniest films, featuring standout performances by Gene Wilder and Zero Mostel. The film’s audacity in turning one of history’s darkest ideologies into a Broadway punchline was shocking at the time and remains genuinely bold even now. It launched Brooks as one of cinema’s great comic minds.
8. This Is Spinal Tap (1984)
Rob Reiner was on an exceptional run in the late 1980s and early 1990s, and his crowning comedic achievement was This Is Spinal Tap. Following a fictional British rock band on a disastrous American tour, this pioneering mockumentary pokes fun at rock-and-roll excess with anarchic glee. The film practically invented a genre that dozens of later comedies would borrow from.
This Is Spinal Tap is a spoof of aging rockers and is partly responsible for the abundance of mockumentaries seen today. A documentary crew follows the fictional band around and chronicles all of their comic foibles. The joke runs so deep that many viewers initially took the film as a genuine documentary, which may be the highest compliment a comedy can receive.
9. Duck Soup (1933)
The Marx Brothers were in peak form when they made Duck Soup, and the result is a film that demolishes any idea that comedy from nearly a century ago can’t land today. Groucho plays Rufus T. Firefly, newly appointed ruler of the fictional nation of Freedonia, navigating diplomatic crises, spy plots, and spectacular nonsense with a machine-gun wit that rarely slows for breath.
The American Film Institute ranked Duck Soup fifth on its list of the greatest comedies . The legendary mirror scene, in which Groucho and Harpo silently mirror each other’s movements in perfect symmetry, is one of the most technically precise pieces of physical comedy ever filmed. It has been imitated by everyone from Lucille Ball to Charlie Chaplin, and it still works completely.
10. Dumb and Dumber (1994)
Dumb and Dumber stars Jim Carrey and Jeff Daniels as Lloyd Christmas and Harry Dunne, two well-meaning but spectacularly dim-witted friends who embark on a cross-country trip to return a lost briefcase. Their outrageous misadventures turn into something ridiculous and life-changing. Carrey, fresh off Ace Ventura, brings his signature physical comedy and elastic expressions to Lloyd, while Daniels was then known for dramatic roles but surprises everyone by diving headfirst into slapstick with total commitment.
Their chemistry is what makes the movie unforgettable. The humor of the film hasn’t aged out of its time. It is still quoted, memed, and loved because underneath all the idiocy, Dumb and Dumber talks about friendship and loyalty, no matter how clueless you are. Few buddy comedies have ever captured the specific, glorious joy of two genuinely good-natured idiots quite so well.
11. The Big Lebowski (1998)
The Big Lebowski was the first modern masterpiece of this kind. The Dude, played by Jeff Bridges, is just a lazy slacker who gets mistaken for a millionaire with the same name. After a slew of kidnapping schemes that ruin his favourite rug, he gets involved in a tangle of conspiracies even though he just wants to bowl.
When it came out in theaters, The Big Lebowski made a modest amount that barely broke even. However, in the years following, the film became a cult classic and a cultural icon, also making a lot of money on home video and streaming. The Big Lebowski can only be described as a surreal comedy noir with a unique protagonist, beloved side characters, and sharp dialogue that make it a cultural comedy landmark.
12. Ghostbusters (1984)
When a team of university parapsychologists find themselves unemployed, they use their expertise in paranormal activity to enter an entirely different line of work: fighting ghosts. After coming across an ancient supernatural threat, the team of Ghostbusters must battle to prevent the end of the world. Ghostbusters is regarded as a classic in the comedy world, and for good reason.
Harold Ramis and Dan Aykroyd’s witty script is jam-packed with quotable one-liners, and a standout performance from comedy all-star Bill Murray makes it sing on screen. This family favourite truly stands the test of time, with its poorly aged special effects only adding to its entertainment value. It’s the rare comedy that works equally well for an eight-year-old and a forty-year-old, for entirely different reasons.
13. The Hangover (2009)
When the first installment of The Hangover trilogy released in 2009, no one expected the impact the movie would have on the comedy genre. Directed by Todd Phillips, the film stars Bradley Cooper, Ed Helms, and Zach Galifianakis as friends who travel to Las Vegas for a bachelor party. When they wake up the following day, they don’t remember a single thing and their friend is missing.
The Hangover became the highest-grossing R-rated comedy ever in the United States. While The Hangover would receive a full trilogy following its massive success, neither of the sequels came close to the comedic highs of the original. The mystery-within-a-comedy structure was genuinely fresh, and the trio’s chemistry felt effortless in a way that proved almost impossible to recreate.
14. Bridesmaids (2011)
When it was released in 2011, Bridesmaids was immensely successful among audiences and critics alike, and became a landmark in cinema history, breaking various box office records. Kristen Wiig stars as Annie, a downtrodden young woman who begrudgingly accepts maid of honour duties when her best friend gets married. Leading the way for a motley gang of bridesmaids, Annie struggles to keep things running smoothly both with the wedding and in her own life.
Writers Wiig and Mumolo ended up bringing in $288.4 million dollars with Bridesmaids, making the film Judd Apatow’s highest-grossing. It is one of the very few full-on comedy films to be nominated for an Academy Award for Best Original Screenplay, finding a brilliant balance between fun, raunchy humor, and genuinely compelling characters with emotional arcs. Its emotional moments never get in the way of the massive comedic highs, as Bridesmaids is a laugh riot from beginning to end.
15. Superbad (2007)
Few comedies capture teenage awkwardness with the same honesty and hilarity as Superbad. Written by Seth Rogen and Evan Goldberg, it follows two high school friends as they stumble through one chaotic night of parties, fake IDs, and botched attempts at romance. It strikes just the right balance of raunch and heart, with every absurd misadventure grounded in a real fear of growing up and growing apart.
As far as coming-of-age comedies of the 21st century are concerned, none have had the undeniable impact and lasting legacy of Superbad, with its distinct style of self-deprecating humor defining a whole generation. Even almost 20 years after its release, Superbad still stands as one of the most relatable teen movie experiences out there, as well as being hilarious from beginning to end.
16. Coming to America (1988)
Eddie Murphy and Arsenio Hall teamed up with director John Landis to create a classic. As Prince Akeem from the fictional African country of Zamunda, Murphy travels to the United States to evade his arranged marriage and find true love in Queens. Akeem encounters all of the wonders of Black America, and the satirical twist is genius, capturing the barbershop, the club scene, hip-hop culture, and more.
Cameos from actors like Cuba Gooding Jr., Samuel L. Jackson, Louie Anderson, and Murphy’s Trading Places co-stars Don Ameche and Ralph Bellamy take the Coming to America experience to a whole new level. Murphy’s ability to play multiple wildly different characters throughout the film is a technical feat as much as a comedic one. It remains one of the most purely joyful comedies Hollywood has ever produced.
17. Office Space (1999)
Office Space didn’t make a huge splash in theaters, but it quietly became one of the most beloved workplace comedies ever made. It’s the story of Peter, an office drone who, after a botched hypnosis session, decides to stop caring about his soul-crushing job. Director Mike Judge had an uncanny eye for the specific, soul-flattening rituals of 1990s corporate life.
Many lines that would seem stale on paper are hilarious thanks to the cast’s phenomenal timing and delivery. Ultimately, Office Space is a film that has only grown funnier as the decades have rolled along. Its satire of corporate emptiness is timeless. The movie resonates because it captures something universally recognizable: the grinding despair of meaningless office life.
18. Young Frankenstein (1974)
Mel Brooks is a living legend, and Young Frankenstein is his best work as a filmmaker. In a loving parody of the Universal horror films of the 1930s, Gene Wilder plays Dr. Frederick Frankenstein, a descendant of the infamous scientist who reluctantly inherits his grandfather’s castle and, inevitably, his obsessions. The film is shot entirely in black and white, mirroring the look of the original monster movies it lampoons.
The attention to period detail gives the film a texture most parodies never bother with, and that commitment to craft makes every joke land harder. The chemistry between Wilder, Marty Feldman, Teri Garr, and Madeline Kahn is something genuinely special. Rotten Tomatoes critics described Mel Brooks’s work here as one of his finest and funniest films. Decades on, it holds up as the gold standard for loving film parody.
19. Shaun of the Dead (2004)
Simon Pegg, Nick Frost, and Edgar Wright emerged from the cult TV series Spaced fully formed to take over the midnight-movie circuit with this daffy, hyperkinetic zombie-romantic-comedy. The quips and sight gags come a mile a minute, but the secret to Shaun’s success is its respect for the source material. This isn’t a parody; it’s a loving homage, complete with sly social commentary in the tradition of George Romero lurking behind the gags.
There’s an effortless balance between laughs, genuine thrills, and touching pathos. That it all looks so effortless is some sort of miracle. Wright’s visual comedy style, where the editing and camerawork are themselves part of the joke, influenced an entire generation of filmmakers. Shaun of the Dead proved that horror and comedy don’t cancel each other out; they can amplify each other in remarkable ways.
20. Borat (2006)
Part satire, part shockumentary, Borat gets high marks almost all around for being offensive in the funniest possible way. Outrageous situations occur when a popular reporter from Kazakhstan comes to the United States to film a documentary. Sacha Baron Cohen’s method of embedding his fictional character into real, unscripted situations produced moments of comedic anarchy that no conventional script could have manufactured.
The film works on multiple levels simultaneously, functioning as slapstick, character comedy, and biting cultural satire all at once. Of all the cinematic genres, comedy is the hardest to truly master. Humor is so context-dependent that many comedies struggle to have a strong, immediate impact. Borat succeeded on every front, delivering laughs that were often uncomfortably revelatory about its real-life participants. It remains one of the most genuinely daring comedies ever put in front of a camera.
What unites these twenty films is not a single style or era but a common commitment to landing the joke, building real characters, and trusting the audience. Even when filmmakers make most of their jokes land, comedies tend to be very topical and context-specific. A small number of comedic gems defy this trend, remaining hilarious years or even decades after release. Their humor transcends a specific time or place. These twenty films belong to that rare category, and they’re well worth revisiting whenever life calls for a genuine, uncontrollable laugh.
