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The 100 best comedy movies: 50-41

The 100 best comedy movies, picked by experts from across film, TV and comedy


When Harry Met Sally… (1989)

‘Don’t fuck with Mister Zero.’

Director: Rob Reiner

Cast: Billy Crystal, Meg Ryan, Carrie Fisher

Defining moment: Billy Crystal’s rant about ageing, mortality, love, divorce and ‘that stupid, wagon wheel, Roy Rogers garage sale coffee table!’ is simply one glittering jewel among many.

It’s a pity that all anyone remembers from Rob Reiner's and Nora Ephron’s ‘more Woody than Woody’ New York romcom gem is that fake-orgasm scene. Sure, it’s a great scene, and very bold for its time. But there’s so much else in the movie to love: those pitch-perfect performances (Bruno Kirby was never better), the gorgeous but unflashy photography and, of course, Ephron’s script, a masterpiece of construction offering wisdom and wit, shock and sweetness, forever sailing this close to mawkishness but always managing to pull back from the brink. Both Ephron and Reiner later sank into Hollywood slush, but they were always headed that way. And at least they left one perfect – and I do mean perfect – movie before they jumped. Tom Huddleston

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Release date: Friday December 11 2015

Love and Death (1975)

‘I was walking through the woods, thinking about Christ. If he was a carpenter, I wondered what he charged for bookshelves.’

Director: Woody Allen

Cast: Woody Allen, Diane Keaton, Georges Adet

Defining moment: As with so many of Woody’s finest films it’s the monologues that matter, and the closing one here is a doozy.

Can I get through this review without using the phrase ‘Early funny one’? Nope, failed already… Placed on a conventional, laughs-per-minute barometer, Woody Allen’s acerbic parody of flatulent Russian literature is probably his funniest film. He plays a weaselly nebbish (natch) called Boris, the bespectacled runt of the chest-beating Grushenko litter who is sent off to the Russian front to fight Napoleon, but doesn’t want to die before declaring his love for his childhood paramour, Sonja (a mad-eyed Diane Keaton). Boasting at least one solid-gold one-liner per scene, the genius of Allen’s film is the way he balances sincere philosophical enquiry into the nature of mortality and the ultimate frivolity of love with some Marx brothers-level slapstick mayhem. Everybody… ‘No, you’re Don Francisco’s sister!’ David Jenkins

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Play It Again, Sam (1972)

‘No, my parents never got divorced. Although I begged them to.’

Director: Herbert Ross

Cast: Woody Allen, Diane Keaton, Tony Roberts

Defining moment: On Diane Keaton’s urging, Woody tries to chat up a girl in an art gallery and discovers she’s the ultimate nihilist: ‘waste, horror and degradation...’

Based on his stage play, this film sees Woody Allen play a neurotic, unlucky-in-love, socially maladjusted film critic who receives life lessons from the ghost of Humphrey Bogart. We’re prepared to forgive Mr Allen’s egregious maligning of film journalists and admit that, yes, this is indeed one of his best movies. Handing the directorial reins to Herbert Ross allowed Allen to deliver one of his funniest performances, and the movie’s clever integration of real life and fantasy anticipates the mature sophistication of films such as ‘The Purple Rose of Cairo’. Edward Lawrenson

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The Apartment (1960)

‘That’s the way it crumbles... cookie-wise.’

Director: Billy Wilder

Cast: Jack Lemmon, Shirley MacLaine, Fred MacMurray

Defining moment: Funny it ain’t, but Shirley MacLaine’s suicide attempt is the moment this bruising urban comedy transforms into something deeper, richer and infinitely more affecting.

The humour in Billy Wilder’s film sits alongside some pointed observations about loneliness and corporate facelessness in 1960s Manhattan. Jack Lemmon appears in one of his greatest roles as CC Baxter, a low-level office employee who lends his apartment out to philandering bosses in return for favours in the workplace. His own romantic life takes a positive turn when he falls for the cute, modish company lift operator, Fran (Shirley Maclaine) – only for his hopes to be dashed in cruel fashion. The jokes are muted, but you can just about call ‘The Apartment’ a comedy as things turn out just about okay in the end – a suicide attempt notwithstanding. Dave Calhoun

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Harold and Maude (1971)

‘Harold, everyone has the right to make an ass out of themselves.’

Director: Hal Ashby

Cast: Bud Cort, Ruth Gordon

Defining moment: When a sweet, romantic scene on a green hillside pulls back to reveal a military graveyard filled with literally thousands of interchangeable white crosses.

Non-genre-specific movies such as ‘Harold and Maude’ have suffered on this list: is it really a comedy? Isn’t there a bit too much death, oppression and holocaust talk for that? But if it’s not a comedy, what is ‘Harold and Maude’? Therein, of course, lies its genius: it’s not anything, except real. And it’s not even that: any film in which a teenage boy commits fake suicide 15 times to shock his unshockable mother can’t really be treated as cinéma vérité. But the film’s feelings are real, its heart is real, and its intention – to reveal a world of non-judgemental freedom and happiness, if only you can let yourself go a little – is the most real of all. This is cinema to treat the soul – and laughter is only a part of that. Tom Huddleston

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Office Space (1999)

‘We need to talk about your flair.’

Director: Mike Judge

Cast: Ron Livingston, Jennifer Aniston, David Herman

Defining moment: Deprived of his beloved red stapler, mumbling Milton is moved downstairs to the basement, as a space-saving measure.

Writer-director Mike Judge has evolved from the lovably crude ‘Beavis and Butt-Head’ to the scalpel-sharp (and still lovably crude) ‘Silicon Valley’. But if there ever was a pivotal moment when this talent – uniquely attuned to corporate banalities – became something major, it’s ‘Office Space’. His film’s drab cubicle culture can be recognised, sadly, by far too many viewers, as can its manically upbeat restaurant, Chotchkie’s, a clear TGI Friday’s slam. After a lousy day, when you feel like something important has been crushed (your soul?), this is the comedy to put on. Joshua Rothkopf

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National Lampoon’s Vacation (1983)

‘I’m on a pilgrimage to see a moose! Praise Marty moose! Holy shit!’

Director: Harold Ramis

Cast: Chevy Chase, Beverly D’Angelo, Randy Quaid

Defining moment: The arrival at Wally World – funny, sure, but somehow deeply upsetting as well.

While one could hardly describe Chevy Chase’s early screen presence as anything like conservative, he did always somehow lend his characters a level of dissipated authority. From Fletch’s unflappable urbanity to Ty Webb’s zen poise in ‘Caddyshack’ to his cocksure stewardship of TV’s ‘Saturday Night Live’, he always seemed in full control. Telling then, perhaps, that when he traded the life of a raffish outsider to become a put-upon suburban family man for ‘Vacation’, the resultant meltdown was both swift and spectacular. Director Harold Ramis and writer John Hughes put Chevy’s Clark Griswold through so many cosmically misaligned hoops in order to get his family to their chosen holiday destination that swollen deeps of bile and fury bubble over into some of the funniest and most memorably deranged rants in all of cinema: ‘This is no longer a vacation. It’s a quest. A quest for fun!’ Adam Lee Davies

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Tootsie (1982)

‘I have a name. It’s Dorothy. Not Tootsie or Toots or Sweetie or Honey or Doll.’ ‘Oh, Christ!’ ‘No, just Dorothy.’

Director: Sidney Pollack

Cast: Dustin Hoffman, Jessica Lange, Bill Murray

Defining moment: Take your pick, because all of Bill Murray’s ranting moments about art and grandeur are magnificent.

Anyone surprised by Bill Murray’s mid-’90s rebirth as a ‘proper’ actor – rather than just a sarcy smart-mouth comic – clearly hadn’t seen ‘Tootsie’. Sure, this is Dustin Hoffman’s show – he’s the one in the dress, after all – but it’s Murray who sticks in the memory, the source of most of the film’s big laughs and a goodly portion of its soul. Looking back, the concept of a guy dressing up as a woman to get a better job is a vaguely uncomfortable one, and its approach to the question of feminism is badly outdated. But the performances still shine, the script still sparkles and director Sydney Pollack’s smooth ’80s style still charms. Now hang on while I fix my lippy. Tom Huddleston

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The Ladykillers (1955)

‘Professor, I must give you back your ten shillings. You see, the cabbie wouldn’t take any money, because he said he was going into some other business.’

Director: Alexander Mackendrick

Cast: Alec Guinness, Peter Sellers, Herbert Lom

Defining moment: The finale, as one by one the thieves are ‘accidentally’ picked off...

This was the great British swansong of both Ealing Studios and director Alexander Mackendrick. For those who haven’t seen it, it’s about a gang of ugly thugs and emollient thieves (led by Guinness’s fake professor) who delude a sweet, guileless old Victorian lady into renting her spare room pretending, naturally, to be classical musicians. Modern critics have – rightly – stressed the barely veiled horror, mordant cynicism and festering substratum lurking behind the innocent-seeming surfaces of American-born Mackendrick’s movies. And ‘The Ladykillers’ is certainly as black as soot: an hysterical movie in more senses than one – which, no doubt, helps it to deliver its series of mischievously satisfying knock-out punches. But its delights are not only satirical: its classical pleasures are plenty. From the inimitable cast to Jim Morahan’s superb art direction and Otto Heller’s luscious early Technicolor cinematography, Mackendrick orchestrates his syncopated instruments with the precision of a Boccherini 'String Quintet', allowing us to bask in the oh-so delectable schadenfreude of watching the meticulous unravelling of yet another of man’s best-laid plans. Wally Hammond

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The Odd Couple (1968)

‘You’re the only man in the world with clenched hair.’

Director: Gene Saks

Cast: Walter Matthau, Jack Lemmon, Herb Edelman

Defining moment: When Matthau snaps – ‘kindly remove that spaghetti from my poker table!’ – it’s both insightful and a little bit scary.

Opened out yet reined in from Neil Simon’s original stage play, this greatest of buddy movies is a beautiful expression of Newton’s third law of classical mechanics: the mutual forces of action and reaction between two bodies are equal, opposite and collinear. The two bodies are sports writer Oscar, an irksome, egotistical slob who is a towering grouch (played with misanthropic self-enjoyment in a career-defining performance by Walter Matthau), and his equally annoying fellow writer and divorcé pal Felix (Jack Lemmon on top form), a man as insecure, neurotic and hypochondriacal as his friend is careless and heartlessly hearty. Oscar invites the suicidal Felix to share his flat and each quickly discovers what makes the other impossible to live with: a clear case of domestic histories repeating themselves, first as tragedy, second as farce. Director Gene Saks’s job was merely to bait his two sparring roosters and let them go. It’s a deeply unedifying spectacle – and still as funny as hell. Wally Hammond

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See numbers 40-31