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Grodin and Shepherd do wonders in making their shallow characters believable, and the fact that charming Ben Stiller and Michelle Monaghan couldn’t do the same in the Farrelly Brothers’ ill-conceived remake is a testament to the tightrope walked by May in her underseen classic. In a masterpiece of awkward tension, Grodin stars as an aloof salesman who suddenly – as in, en route to the honeymoon – realises his new bride (Jeannie Berlin, May’s real daughter) is the absolute worst, then promptly falls for another guest (Cybil Shepherd) while his unsuspecting spouse heals from a bad sunburn. In a just world, her Heartbreak Kid would be her calling card – a proto cringe comedy from the pen of Neil Simon that features one of the best jittery performances of Charles Grodin’s career. Improv pioneer Elaine May completely changed comedy through her influential stage work with Mike Nichols, yet as a director she’s mostly associated with the unfairly maligned mega-bomb Ishtar. ‘They should have warned us that there was a danger of running out of pecan pie.’Ĭast: Charles Grodin, Cybill Shepherd, Jeannie Berlin And if you don’t find something to bring the chuckles, well, there are 99 more options where that came from. Next time you need something to turn that frown upside down, you’ll know where to start. To help us with the task, we enlisted the help of comedians (such as Russell Howard and Diane Morgan), actors (John Boyega and Jodie Whittaker, among others), directors and screenwriters (including Richard Curtis), as well as several generations worth of Time Out writers. That makes choosing the 100 best comedies of all time a little tricky. And that’s to say nothing about comedy being the hardest genre to translate across cultural divides, class strata and generations. And they need to do it effortlessly, because once a comedy shows signs of straining for a joke, the audience checks out. No matter the flavour – romcom, satire, gross-out, teen, screwball – they need to hit their punchlines with deadly precision.

Thrillers and action flicks can appeal directly to the adrenal gland. A great horror film can tap a universal fear to be effective. Of all film’s genres, comedy might be the hardest to nail.

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