Sondheim's Cinema: 31–40 of His Favourite 40 Films

Continuing my journey through Stephen Sondheim’s top 40 films, numbers 31–40 offer another diverse batch of international cinema, from gripping political dramas to tense character studies and meditations on mortality. Alongside these, I watched bonus screenings celebrating Sondheim’s love of puzzles, performance and storytelling itself.

31/40: The Official Story (1985, Luis Puenzo, Argentina) In Buenos Aires during the final days of the military dictatorship, a history teacher (Norma Aleandro) begins to suspect that her adopted daughter may be the child of a disappeared political prisoner. A gripping and devastating political drama about complicity, memory and truth. Winner of the Oscar for Best Foreign Language Film, it remains a powerful reminder of Argentina’s “Dirty War” and its enduring scars.

32/40: The Nasty Girl (1990, Michael Verhoeven, West Germany)

A sharp, provocative satire based on a true story. When a bright student researches her town’s Nazi past, she discovers how deep denial and hypocrisy still run. What begins as curiosity turns into defiance as the community closes ranks against her. Smart, unsettling and darkly funny, it skewers collective guilt with precision and nerve.

33/40: Adam’s Rib (1990, Vyacheslav Krishtofovich, Russia) I couldn’t find a copy to watch, but it appears to be a character-driven comedy-drama exploring domestic tensions and gender dynamics in contemporary Russia. Despite not seeing it, it seems to reflect Sondheim’s interest in human relationships and clever, observational storytelling.

34/40: The Oak (1992, Lucian Pintilie, Romania)

A raw, unsettling portrait of post-Ceaușescu Romania, following a young teacher and a weary doctor through a society still scarred by its past. Bleakly funny and quietly chaotic, it captures the confusion and exhaustion of a country trying to find meaning after collapse.

35/40: Fresh (1994, Boaz Yakin, USA) In Brooklyn’s unforgiving streets, 12-year-old Fresh (Sean Nelson) navigates a world of drug dealers, violence and survival. But he’s always thinking a few moves ahead. Drawing lessons from chess games with his father (Samuel L. Jackson), he crafts a plan to outsmart everyone trapping him. Fresh is tense, gritty and impressively controlled for a debut feature. It flips the crime genre into something more cerebral and haunting, with a quiet, devastating ending.

36/40: Lone Star (1996, John Sayles, USA)

In a dusty Texas border town, the discovery of a long-buried skeleton pulls Sheriff Sam Deeds (Chris Cooper) into the shadows of his father’s legacy. Sayles weaves past and present together with remarkable ease, creating a slow-burn mystery that deepens into a study of community, memory and the stories people choose to believe. Beautifully acted, richly textured and quietly political, Lone Star feels both intimate and sweeping.

37/40: Henry Fool (1997, Hal Hartley, USA) Henry (Thomas Jay Ryan), a brash and self-serving drifter, pushes a timid garbage man Simon (James Urbaniak) to unleash his hidden writing talent. Parker Posey is eccentric as Henry’s sister Fay, who becomes his ‘love interest’. The dialogue is witty at times but often pretentious, and the pacing drags so the quirky charm wears thin. Interesting in parts but not my vibe.

38/40: Character (1997, Mike van Diem, Netherlands)

Set in 1920s Rotterdam, a determined young law student struggles with his domineering father. Framed partly as a mystery, the film gradually reveals how pride, ambition and resentment shape both men. Carefully structured and compellingly told, Character balances emotional intensity with narrative precision. Absorbing and thoughtfully made.

39/40: Elephant (2003, Gus Van Sant, USA) Loosely inspired by the Columbine shooting, the film drifts through the corridors of an American high school in long, hypnotic takes, observing students on an otherwise ordinary day before violence erupts. Minimalist and distancing, it resists easy explanation. The final stretch brings a chilling clarity that re-contextualises what came before.

40/40: The Barbarian Invasions (2003, Denys Arcand, Canada)

A thoughtful, bittersweet exploration of life, death and the generational divide. As terminally ill Rémy faces his final days surrounded by friends and family, the film mixes sharp social commentary with humour, reflecting on politics, culture and personal legacy. Intelligent and often moving, though uneven in tone at times.

Bonus Watches

Sondheim as a Character Double Bill

Blue Moon (2025, Richard Linklater) Richard Linklater’s latest unfolds over a single night in 1943, following lyricist Lorenz Hart on the opening night of his former writing partner Richard Rodgers’ Oklahoma!. What initially feels like a small, contained setup gradually opens out into a layered portrait of Hart’s personal and professional life, capturing both his brilliance and his isolation at a pivotal moment.

Among those who drift into Hart’s orbit on this auspicious evening is “Little Stevie” Sondheim (Cillian Sullivan), attending the Oklahoma! after-show party at Sardi’s as a family friend of Oscar Hammerstein II. Sondheim appears as an eager Broadway nerd, sharp-eyed and opinionated, already critical of Rodgers and alert to the shifting tides of American musical theatre.

tick, tick… BOOM! (2021, Lin-Manuel Miranda)

Jonathan Larson’s semi-autobiographical musical comes alive with Andrew Garfield as the struggling composer racing to finish his first show before turning 30. Bradley Whitford plays Sondheim in a few scenes, and the real Sondheim leaves a touching voicemail cameo, reflecting his generosity and mentorship.

A Sondheim Murder-Mystery Double Bill

Glass Onion (2022, Rian Johnson)

A glossy, sun-soaked whodunnit that follows master detective Benoit Blanc (Daniel Craig) as he unravels a tech billionaire’s elaborate game on a Greek island. Sondheim makes a brief cameo on a Zoom call with Blanc, Angela Lansbury, Natasha Lyonne and Kareem Abdul-Jabbar, all playing Among Us during lockdown. The cameo nods to Sondheim’s lifelong love of puzzles and to The Last of Sheila, the 1973 mystery he co-wrote with Anthony Perkins that inspired Johnson. The film is dedicated to both Sondheim and Lansbury.

The Last of Sheila (1973, Herbert Ross)

A sharply constructed yacht-set mystery co-written by Stephen Sondheim and Anthony Perkins. Full of games, secrets and twisty reveals, it remains one of the cleverest whodunnits of its era and a clear precursor to Johnson’s modern murder-mystery style.

Recurring Threads Across Films 31–40

• Political and Social Consciousness – The Official Story, The Nasty Girl and The Oak confront historical trauma, collective guilt and societal collapse, reflecting Sondheim’s interest in human accountability.

• Mortality and Intergenerational Tension – Lone Star, Character and The Barbarian Invasions explore legacy, pride, mortality and familial obligation.

• Survival and Strategy – Fresh and Henry Fool highlight cleverness, resilience or ambition in challenging environments.

• Form, Precision, and Tension – Elephant demonstrates formal control and measured narrative, exemplifying the structural inventiveness Sondheim admired.

These threads reveal Sondheim’s attraction to films that combine moral, social or artistic weight with formal or narrative precision, often pairing stark realism with insight into human character.

Closing Note

The list of Stephen Sondheim’s top 40 films list was drawn up in 2003, when he served as guest director for the Telluride Film Festival in Colorado. It seems he selected films he loved from his own “moviegoing period” to share with young people attending the festival who might not be familiar with the work of these directors. This also helps explain why the final two films on the list date from 2003.

A year-end round-up post will follow, reflecting on all 40 films, my bonus watches, and my attempts to catch up with the Sondheim musicals I’d previously missed on stage in 2025 - a year that also coincided with the London premiere of his final musical, Here We Are, at the National Theatre.

I’ll also be sharing my plans for what comes next.