The hardest thing to make
Anybody can make you cry. Grief is easy to trigger: kill a dog, separate two people who love each other, slow the music down. Comedy is harder. It requires precision timing, genuine surprise, and a writer willing to humiliate themselves on the page before anyone has to do it on camera. The best comedies are built on the same structural bones as the best thrillers. They just use those bones to make you spit your drink.
This is not a listicle of things that are broadly considered amusing. These are the works that land: the ones with a genuine point of view, where the jokes arrive because the characters are real and the world has internal logic, not because someone typed FUNNY THING HERE in the script. Across film, TV, games, and books, these are the comedies that reward rewatching, rereading, and replaying.
The all-time film canon
The benchmarks every comedy gets measured against, whether it wants to be or not
Satire peaked in 1964 and we have not recovered
Dr. Strangelove remains the funniest and most accurate film ever made about institutional men deciding the fate of the world. Kubrick understood that satire works when it treats absurdity with complete seriousness: nobody in that war room is winking at the camera. The horror and the comedy are the same thing. Every political comedy made since has been trying to catch up to a film where the punchline is the end of civilization, delivered without a single raised eyebrow.
The TV comedies that changed the form
Series that rewrote what a sitcom was allowed to do
Fleabag is a one-person proof that comedy and grief are the same emotion
What everyone misses about Fleabag is that it is not brave for mixing comedy with sadness. That combination is old. What Phoebe Waller-Bridge did that was genuinely new was make the fourth wall break a structural element of the grief, not just a gimmick for laughs. The moment the camera cuts away from the audience to find the priest standing there, looking back at us, the whole architecture of the show collapses into itself. That is a comedy writer operating at the very edge of what the form can do.
A short history of screen comedy
- 1926Keaton's The General establishes that physical comedy can be formally perfect and genuinely dangerous The General
- 1940Screwball peaks: His Girl Friday runs so fast it invented modern comic dialogue His Girl Friday
- 1959Some Like It Hot proves you can end a comedy on a joke that is also a thesis Some Like It Hot
- 1964Kubrick turns the Cold War into the century's sharpest satirical film Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb
- 1975Python builds absurdist medieval chaos into a film that aged to pure gold Monty Python and the Holy Grail
- 1980Airplane! invents the parody-as-speed-run format; nothing since has matched the jokes-per-minute Airplane!
- 1993Groundhog Day disguises a philosophical novel as a comedy starring a weatherman Groundhog Day
- 1998The Larry Sanders Show ends its run as the most sophisticated portrait of television ever made The Larry Sanders Show
- 2003Arrested Development front-loads three seasons of callbacks into a structure no network comedy had tried Arrested Development
- 2016Fleabag at Edinburgh; two years later the TV version rewires what a comedy can carry Fleabag
- 2022The Rehearsal makes the most unsettling and funniest television programme about sincerity ever produced The Rehearsal
The sharp and the strange: films that go their own way
Comedies with a distinct vision that resisted easy categorisation on release
The best comedy games are about bureaucracy, not jokes
The funniest games are almost never the ones trying hardest to be funny. Papers, Please is one of the most oppressive and absurdly comic experiences in the medium: you are a border officer stamping documents in a dying authoritarian state, and the comedy emerges entirely from the gap between the bureaucratic mundanity and the human tragedy on the other side of the window. Untitled Goose Game works the same way. Give players a simple anti-social goal, build a world with internal logic, and watch them find the jokes themselves. This is the medium's actual comedic superpower and most game writers keep ignoring it.
Games that are actually funny
Not comedy-adjacent, not 'has some jokes': laugh-out-loud funny as a core quality
The underrated TV pile
Catastrophe, Sharon Horgan and Rob Delaney's series about two deeply ordinary people making a go of a relationship, is better than most of its reputation suggests: it is a comedy about adults, written by adults, that never condescends to its characters or its audience. What We Do in the Shadows (the TV series) improved on the film by giving itself space to develop its idiots into something approaching genuine characters. And The Rehearsal, Nathan Fielder's HBO series from 2022, is a genuinely singular piece of television that does not fit inside any genre comfortably and is funnier for it.
On the British side, I'm Alan Partridge remains Steve Coogan's peak: a character study of a specific kind of provincial male ego, delivered with such precision that it transcends parody and becomes something closer to tragedy. People who only know Partridge from the later films are missing the actual work.
TV worth finding that does not get enough credit
The ones you mention and people say they mean to watch, then do not
The best comedy writers understand that a joke is just a small argument with reality. You set up an expectation, then you violate it in a way that feels both surprising and inevitable. That feeling of inevitability is the whole trick.CrossBinge Editorial
Catch-22 is a war novel but the war is just the joke's delivery mechanism
Catch-22 is shelved in war fiction but Heller was doing something specific: he was writing a structural comedy about the impossibility of rational behaviour inside an irrational system. The circular logic of the title is funnier the longer you stare at it, and also more terrifying. The book's reputation as dense and challenging obscures how relentlessly, mean-spiritedly funny it is on a sentence level. Heller hated stupidity with a genuine passion and it shows on every page.
A note on the Adams problem
Douglas Adams is the single most quoted comedy writer in English and one of the least read. Everyone knows 'the answer is 42' and almost nobody has read the three chapters in The Hitchhiker's Guide to the Galaxy that set up that joke with actual precision and care. Adams was doing something philosophically real inside the comedy: he was making an argument about the absurdity of searching for meaning in a universe that did not generate questions to match its answers. The joke is funnier if you understand the argument. The argument is more convincing because it is expressed as a joke. This is what the best comedy does and why it is worth taking seriously.