A divorced socialite (Grace Kelly) finds her affections caught between her ex-husband (Bing Crosby), her new fiancée (John Lund), and a tabloid reporter (Frank Sinatra) in Charles Walters’ musical comedy High Society (1956). It is a remake of George Cukor’s The Philadelphia Story (1940), adding in a string of Cole Porter songs and embracing the then-hugely popular jazz scene via supporting performer Louis Armstrong.

As is the case with most films both popular and old, High Society is generally regarded as a classic. It is always worth interrogating that claim with films from Hollywood’s Golden Age, since viewers tend to automatically associate ‘old’ with ‘good’, and that is not always the case. High Society, which boasts a stand-out cast of famous talent and a few hugely memorable songs, ostensibly deserves the classic label. That said, the film has to work to get there: the first half of the film really does not stand up to the quality of the second, and it never quite matches the original work.

Grace Kelly makes her final professional film appearance here, and while she seems a little out of place – a non-singing protagonist in a Hollywood musical feels like a miscasting – she demonstrates a tremendous gift for comedy. As is always the case with Kelly, she also wears designer clothing like nobody in cinema before or since.

By contrast, Sinatra feels entirely comfortable. When paired with Gene Kelly in earlier MGM musicals he seemed hamstrung by having to dance opposite one of the all-time greatest dancers. Here he is in his element: a superb singer and musical performer, his character is a perfect fit and an absolute delight. He is paired for much of the film with Celeste Holm, an immensely talented and engaging performer. Their light-hearted duet “Who Wants to be a Millionaire” stands as one of the film’s highlights.

The other highlight is the charming and funny “Well Did You Evah”, pairing Sinatra with male co-star Bing Crosby. High Society captures Crosby closer to the end of his career than the beginning, and while he perhaps feels a little more relaxed and understated here than in earlier roles he remains a winning talent and a wonderful vocalist. Supporting actors including Lund (perfectly humourless), Margalo Gillmore, and particularly Louis Calhern (who died between shooting the film and its release) all make strong, engaging contributions.

It really is the second half of the film that shines: the pre-wedding party, everybody getting too drunk, Crosby and Armstrong singing jazz, the bride climbing out of windows and falling into swimming pools, and finding herself caught between two romantic suitors – neither of whom is her fiancée. These days High Society requires a little patience to reach its best parts, and it is very clear that it fails to embrace either jazz culture or class issues in the way that it could, but as a work of 1950s populist entertainment it still delivers the goods.