01 Monty Python and the Holy Grail
“Are you suggesting coconuts migrate?” There must and shall be Python. A seriously close call between Grail and The Life of Brian, but the Knights who say Ni!, a stack of earworm songs and killer rabbits swing it.
“Looks like I picked the wrong week to quit sniffing glue.” For spoofing the entire genre of disaster films; ridiculously over-packed with jokes and for the jive-talking nun. For reals.
03 In Bruges
“A great day this has turned out to be. I’m suicidal, me mate tries to kill me, me gun gets nicked and we’re still in fucking Bruges.” Beautifully farcical, funny and rather violent. Shoot first. Sightsee later.
04 Dr. Strangelove
“Gentlemen, you can’t fight in here! This is the War Room!” Kubrick and scriptwriter Terry Southern took the decidedly not-funny book Red Alert by Peter George and made a satirical masterpiece out of a nuclear disaster. Black humour doesn’t get a lot darker than that. Genius.
05 Harold and Maude
“Harold, everyone has the right to make an ass out of themselves. You just can’t let the world judge you too much.” Dark as hell and bleakly funny… just like life. Hal Ashby’s 1971 tale of a suicidal teenager and an anarchist octogenarian is an art house favourite.
06 Team America
“[Paris is reduced to a smoldering pile of rubble.] Bonjour, everyone! Don’t worry. Everything is bon! We stopped the terrorists.” It is next to impossible to find a quote from the film which doesn’t make it seem devoid of context, outright racist and a bit sweary, but then that’s the point. It’s Trey Parker and Matt Stone flipping the bird at just about everyone and it’s very funny. Also there are songs.
“I saved Latin. What did you ever do?” Wes Anderson hasn’t out-funnied this fiercely eccentric film from 1998. Note perfect and perfectly off-kilter.
08 Cold Comfort Farm
“I saw something nasty in the woodshed!” Stella Gibbons’ parody of mawkish Victorian novels benefits from the big screen efforts of an amazingly classy cast; Stephen Fry’s oozing Mybug, Ian McKellen’s Amos Starkadder and the Quivering Brethren are particular highlights.
“Gozer the Gozerian? Good evening. As a duly-designated representative of the City, County and State of New York, I order you to cease any and all supernatural activity and return forthwith to your place of origin, or to the next convenient parallel dimension.” Big special effects and dialogue that’s acerbic, goofy and damned intelligent.
10 Animal House
“TOGA! TOGA!” It would be easy to write this film off as a vulgar, frat-boy fest, and it has fathered a ridiculous number of poor quality, gross-out knock-offs, but there’s quality here. Honestly. Directed by John Landis and co-written by Harold Ramis, filled with nuanced performances and an incredible turn by John Belushi.
11 This is Spinal Tap
“These go to 11…” The satirical “rockumentary” that spawned the mockumentary genre. Combusting drummers, the Smell The Glove album and a tiny henge. Epic.
“Take care of the squirrels.” The performances of Donald Sutherland and Elliott Gould are what makes this film; both naturally funny men, without them I think the cruelty and bloody theatre (of both war and operating) of this film would be overwhelming.
13 Dark Star
“Bomb, this is Lt. Doolittle. You are not to detonate in the bomb bay. I repeat, you are NOT to detonate in the bomb bay!” Mustachioed hippies in space, talking bombs, a beachball alien and an underlying subtext on the disillusioned ideals of the 60s make this the seminal, low-budget sci-fi comedy its director John Carpenter has described as: “Waiting for Godot in space”.
14 Office Space
“I did absolutely nothing and it was everything I thought it could be.” Pitch-perfect lampooning of the Dilbert-esque horrors of corporate office occupancy. Never have so many felt the collective joy of taking a baseball bat to a printer.
15 Despicable Me
“When we got adopted by a bald guy, I thought this would be more like Annie.” Hitting that sweet spot between being satisfying for adults and children, the Despicable Me films are laugh-out-loud funny and touching, as bald supervillain Gru swaps world domination for fatherhood.
16 Noises Off
“Am I in Spain? No I’m not in Spain, dear. I’m in agony, that’s where I am!” A gorgeously crafted farce based on the Michael Frayn play. Featuring the last performance of Denham Elliott, it’s famed for its complex staging and smart delivery and timing.
17 Little Miss Sunshine
“Everybody just pretend to be normal.” The comedy road trip movie with a strong ensemble cast detailing the dynamics of a dysfunctional family. Contains one of the best talent contest scenes ever.
18 Thank You For Smoking
“The great state of Vermont will not apologize for its cheese!” Takes a cynical stab at the American pro-smoking lobby and tobacco industry.
19 In The Loop
“Climbing the mountain of conflict’? You sounded like a Nazi Julie Andrews!” Will the US President and the UK Prime Minister get the war they’re wanting? This is the big-screen treatment spinmaster Malcolm Tucker deserved.
20 In a World
“This Wednesday, one woman will teach another woman to sound a little less retarded.” Exploring the chauvinism of Hollywood through the medium of trailer voiceovers, Lake Bell’s directing, writing and starring debut is clever and caustic.
21 Shaun of the Dead
“Ohh, for God’s sake! He’s got an arm off!” A romantic comedy. With zombies. Brilliant.
22 Man Bites Dog
“If you kill a whale, you get Greenpeace and Jacques Cousteau on your back, but wipe out sardines and you get a canning subsidy!” Extremely dark Belgian comedy taking the found footage format to a new level as a camera crew on the tail of a serial killer get a little too involved.
“This is your receipt for your husband… and this is my receipt for your receipt.” When administrative errors kill.
“A flute without holes, is not a flute. A donut without a hole, is a Danish.” Will forever change the way you drink tequila, play golf and deal with vermin.
25 The Princess Bride
“Hello. My name is Inigo Montoya. You killed my father. Prepare to die.” The swashbuckling postmodern fairytale to end all others.
26 The Producers
“Not many people know it, but the Führer was a terrific dancer.” The funniest of all the Mel Brooks movies has Gene Wilder and Zero Mostel in fine form, but also the enduring legacy that is Springtime for Hitler.
27 Four Lions
“Is he a martyr or is he a Jalfrezi?” Chris Morris’s satirical black comedy about incompetent suicide bombers is a brilliant jibe in the vein of Charlie Chaplin’s 1940 swipe at Hitler in The Great Dictator.
28 Blazing Saddles
“You’ve got to remember that these are just simple farmers. These are people of the land. The common clay of the new West. You know… morons.” Still one of the best endings in film history.
29 The Big Lebowski
“That rug really tied the room together.” The Dude, otherwise known as a laid-back, White Russian-drinking Jeff Bridges, abides. This cult classic sees the Coen Brothers making something even more impressive than Fargo and inadvertently creating a new religion – Dudeism.
30 Withnail & I
“My thumbs have gone weird.” The melancholy, hysterical genius of Bruce Robinson’s screenplay and the never-beaten big-screen performances of Paul McGann, Richard E Grant and Richard Griffiths. Featuring drugs, drink and more drugs ‒ still a favourite with students.
31 All About Eve
“Fasten your seatbelts, it’s going to be a bumpy night!” Not strictly a comedy, this is a drama with some of the wittiest lines in Hollywood history and an incredibly intelligent and sophisticated cast, led by Bette Davis in shining form.
32 Rosencrantz And Guildenstern Are Dead
“Well, we can do you blood and love without the rhetoric, and we can do you blood and rhetoric without the love, and we can do you all three concurrent or consecutive. But we can’t give you love and rhetoric without the blood. Blood is compulsory. They’re all blood, you see.” Tom Stoppard’s inspired play has Tim Roth and Gary Oldman as the doomed bit-part players in someone else’s (Hamlet’s) life; poignant and sharp.
33 Tropic Thunder
“Man, I don’t drop character ‘til I done the DVD commentary.” An outstanding cameo by Tom Cruise and what is undoubtedly (next to Tony Stark) one of Robert Downey Jr’s most excellent roles and a great satire of film making and the Hollywood machine.
34 South Park: Bigger, Longer and Uncut
“Remember what the MPAA says; horrific, deplorable violence is okay, as long as people don’t say any naughty words! That’s what this war is all about!” A foul-mouthed diatribe against censorship and the Baldwin brothers that also manages to be one of the best musicals of all time. Well, what would you expect from the writing team behind The Book of Mormon?
35 A Shot in the Dark
“Give me ten men like Clouseau and I could destroy the world.” Peter Sellers was a last-minute casting for the role of the intellectually challenged Inspector Clouseau in the first Pink Panther film; the second instalment in the series gives him the space to expand on an iconic comedy character.
“This is a job for the Australian!” Former clowns and cannibalism in a Paris apartment. It’s a dark and magical mash up from the future by the men who brought you Amelie. A feast for the eyes, and morbidly funny.
37 Troll Hunter
“Troll!” Keeping the “found footage” tradition of Blair Witch alive in an original way only the Norwegians could. Self aware, but no less smart for it – this is a far better film than you’d expect.
“Y’know, people are always putting New Jersey down. None of my friends can believe I live here. But that’s because they don’t get it: I’m living in a state of irony.” Unreservedly a film which comes with guidance notes and is adults only, Happiness (starring the late, great Seymour Hoffman) delves into depravity and loneliness to explore how we connect to each other as people. I realise that this in no way sells it as a winning comedy – but marvellously, it is.
“I don’t believe in hell. I believe in unemployment, but not hell.” This film gets it so right, hitting multiple notes including bittersweet romance and social commentary, while taking a jab at sexism. It also manages to avoid the clichéd pitfalls of drag.
40 Groundhog Day
“This is one time where television really fails to capture the true excitement of a large squirrel predicting the weather.” Gave the world back a fighting funny Bill Murray and blew the stock 80s comedy format out of the water by actually having something worth saying about the human condition.
41 The Room
“You’re tearing me apart, Lisa.” Unintentionally hysterical, The Room was voted the worst film ever and became an instant cult comedy by accident.
“I’m in a glass case of emotion!” This sleazy 70s slapstick gave the world the manly Sex Panther cologne, the immortal line, “I love lamp”, and a street fight between local news crews during which a man is killed with a trident.
Kate Mew is Libertine’s Editor at Large. @katemew