(Published by The Culture Trip. Read the full article at their website.)


Chicago in the movies often acts as a cipher rather than a city. It is a place of underground jazz clubs, stylised mob violence – a gangster’s paradise. This Hollywood version of a Chicago certainly does not exist now (and may never have done). As Doris Day put it in ‘Calamity Jane’, ‘the Windy City is mighty pretty’ and we give you ten movies that more than testify to that statement.



‘A whoopee spot/ where the gin is cold but the piano’s hot’. Although Velma Kelly (Catherine Zeta-Jones in an Oscar-winning performance) is singing about a specific club in the opening song to ‘Chicago’, she might as well be singing about the city as a whole. Despite ostensibly being the story of two murderers and their desperation to be famous, the sumptuous jazz age design makes the city of the title seem infinitely appealing – all hot jazz, cool neon and street smarts, a place where half of Chicago are basking in the late night glamor of jazz bars and dancing girls.

High Fidelity

Transferred from the London of the original Nick Hornby book to Chicago, ‘High Fidelity’ paints the city as one of record stores, small gigs and relatable losers, painting a very accurate Chicago just before the millennium. The screenwriters chose Chicago as it was a city they knew well, and whose rich alternative music scene they knew well, and both of these facts are evident in the final film. And when obsessive record shop workers Barry and Dick (Jack Black and Todd Louiso) spend so much of the film making lists, they would be pleased to know they have made the top ten.

Little Caesar

One of the first gangster films ever made (and the fifth film of director Mervyn LeRoy’s nearly 40 year career), ‘Little Caesar’ paints a Chicago where people come to make their fortunes but quickly find themselves led astray. Yes, that sounds like a cliché, but only because ‘Little Caesar’ invented the cliché as well as most of the tropes of the gangster genre. Although the Chicago it depicts no longer exists (some may doubt it ever did), it is a glorious depiction of a salubrious (and dubious) past.

Read the full list, including classic films like Ferris Bueller’s Day Off, The Blues Brothers and When Harry Met Sally at The Culture Trip website.

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