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Sondheim's Cinema: 21–30 of His Favourite 40 Films

  • Writer: Ellen Cheshire
    Ellen Cheshire
  • Sep 23
  • 4 min read

Mandy Patinkin and Madonna in Dick Tracy
Mandy Patinkin and Madonna in Dick Tracy

Continuing my journey through Stephen Sondheim’s top 40 films, I have watched numbers 21–30, revealing another diverse batch of international cinema from bleak anti-war dramas to playful mockumentaries and films about films. Alongside these, I also caught up with another stage work that I'd never seen and some bonus screenings that enrich my annual project celebrating all things Sondheim.

21/40: Fires on the Plain (1959, Kon Ichikawa, Japan) A brutal, unflinching portrait of a Japanese soldier’s descent into starvation and madness in WWII’s final days. This anti-war masterpiece strips conflict of all glory, bleakly beautiful and emotionally searing. Hard, important work, just like its subject.


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22/40: High and Low  (1963, Akira Kurosawa, Japan) A kidnapping gone wrong leads to a tense exploration of morality, class and justice. Gripping, subtle, stylish and sharply structured, a first-time watch that blew me away.


Bonus: Dick Tracy (1990, Warren Beatty, USA) Taking a detour from Sondheim’s list to catch this one, featuring five songs by Sondheim for Madonna’s nightclub character Breathless. Looks good but ultimately disappointing. But you do get Mandy Patinkin and Madonna singing Sondheim (see link below).

23/40: The Organiser (1963, Mario Monicelli, Italy) Marcello Mastroianni plays a wandering professor aiding textile workers’ strike in 19th-century Turin. Socially conscious, humane, blending realism with wit and elegant cinematography.


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Bonus Watch: A Funny Thing Happened on the Way to the Forum (1966, Richard Lester, UK/USA) A chaotic adaptation of Sondheim’s Broadway debut, full of slapstick and visual gags. Only a few songs survive the stage-to-screen transition, but the energy of Zero Mostel and cast makes it a messy delight. Watched following seeing a live production (see below).


24/40: Au Hasard Balthazar (1966, Robert Bresson, France) The tragic life of a donkey mirrors that of Marie, a girl crushed by cruelty. A bleak, haunting reflection on innocence, suffering and the fleeting nature of kindness.


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25/40: War and Peace  (1967, Sergei Bondarchuk, USSR)

Sondheim chose Bondarchuk’s monumental adaptation of Tolstoy, but I was unable to find a copy to watch. Famously vast in scale, it runs over seven hours, with thousands of extras recreating the Napoleonic Wars, and is often cited as one of cinema’s greatest historical epics. One to keep hunting for.

26/40: Bang the Drum Slowly (1973, John D. Hancock, USA) Baseball teammates Henry (Michael Moriarty) and Bruce (Robert De Niro) play out a season while Bruce faces terminal illness. Thoughtful but not for me.

27/40: A Slave of Love (1976, Nikita Mikhalkov, USSR) During the Russian Civil War, a film crew shooting a silent melodrama faces revolution, blurring staged romance and real danger. Strange, uneven yet magnetically cinematic, especially for silent-film lovers.


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28/40: The Elephant Man  (1980, David Lynch, UK/USA) The haunting true story of John Merrick (John Hurt) rescued from a freak show by Dr Treves (Anthony Hopkins). A profound exploration of dignity, humanity and acceptance.

29/40: The Contract (1980, Krzysztof Zanussi, Poland) A wedding that never happens becomes a stage for restless guests circling in ego games and quiet despair. Leslie Caron glides elegantly through unease and disillusion. Clever satire but it did not stay with me.

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30/40: This Is Spinal Tap  (1984, Rob Reiner, USA) The definitive mockumentary of a rock band’s hilariously disastrous tour. Sharp, absurd, endlessly quotable and still brilliant decades later.



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Stage Interlude Alongside these films, I saw A Funny Thing Happened on the Way to the Forum live at The Roman Theatre, Verulamium. Experiencing Sondheim’s chaotic Roman comedy in an authentic ancient amphitheatre created a thrilling dialogue between stage and space, making the humour, spectacle and historical context feel vividly alive. Revisiting Sondheim on stage and screen deepens the cinematic journey, revealing the playful, theatrical energy that threads through both his musicals and his favourite films.

Recurring Threads Across Films 21–30

Watching this next group of films, patterns emerge in the themes and ideas that caught Sondheim’s eye:

Bleakness and Endurance – From the starving soldier in Fires on the Plain to the suffering donkey in Au Hasard Balthazar, survival is depicted without sentiment, stripping existence down to its harshest truths.

Morality and Social Critique – High and Low, The Organizer and The Contract each use their settings to probe questions of justice, class and responsibility, exposing the hypocrisies of social structures.

Entertainment and Art Reflecting Itself – A Slave of Love blurs staged melodrama and political reality, while This Is Spinal Tap parodies the very form it imitates. Both show Sondheim’s interest in works that hold a mirror to performance, storytelling and spectacle.

Mortality and Fragility – The tender friendship of Bang the Drum Slowly and the dignity reclaimed in The Elephant Man return us to questions of vulnerability, decay and death, whether faced with quiet compassion or physical deformity.

Together, these threads reveal Sondheim’s attraction to films that combine formal precision with moral weight, often pairing stark depictions of suffering with sharp social or artistic commentary.

More soon as I continue with films 31–40 #SondheimOnSunday



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