Film
Havana
A 1990 romantic drama set during Cuba's revolution, following an American gambler who arrives in Havana chasing high-stakes poker games and dangerous passion. Sidney Lumet directs a lush, atmospheric film that uses political upheaval as backdrop for intimate human stakes. Best approached as a character study in temptation rather than a thriller.
Should you watch it?
Watch it if you love sprawling, old-fashioned romances where a grand historical backdrop, gambling-table tension and a slow-burning affair against political upheaval are the whole point, and you don't mind lingering over them.
Skip it if you want brisk plotting or a tight runtime, since at well over two hours it moves at a leisurely clip and its romance takes its time getting to the heart of things.
What it asks of you: Settle in for a long, unhurried film with a stately rhythm, where scenes breathe and atmosphere carries as much weight as the dialogue.
Not sure? Find tonight's pick in a minute.
If you liked this
Casablanca1943
The ultimate prototype for this story: exile, impossible romance, moral choice, and intrigue unfolding in a bar during wartime. Bogart's performance sets the standard for the roguish charmer caught between worlds.
But At 102 minutes it moves slowly by modern standards, and the gender dynamics are entirely of its era. Some of the supporting performances haven't aged equally.

The Last Temptation of Christ1988
Scorsese's Lumet-adjacent deep dive into forbidden desire and moral anguish. Matthew Dillon and Willem Dafoe bring raw, uncomfortable intensity to a character wrestling with earthly temptation and larger responsibility.
But Aggressively slow, theologically provocative, and nearly three hours. It's challenging in ways that feel almost oppressive rather than entertaining.

Out of Africa1985
Sweeping, romantic, achingly beautiful cinematography of a colonial world in flux. Streep and Redford again, but exploring how privilege and love collapse when history overtakes personal life.
But Nearly four hours, operatic in tone, and the pacing assumes patience you might not have after a long day. The romance doesn't fully earn its ending.

Not sure tonight? Get a pick in a minute, starting from Havana
The wildcard
Something you would not have found on your own.
Memories of Murder2003
Both use personal story—romance, ambition, desire—as the lens through which to examine a larger historical moment. Both argue that individual choice is constrained by forces larger than the self.
Bong Joon-ho's masterwork: a serial killer hunt in 1980s South Korea that is simultaneously procedural and political, noir and tragicomedy. Brutal, intelligent, and constantly surprising in register. The final 10 minutes will hollow you out.
But Subtitled, graphic violence, and a refusal to provide catharsis. The tonal shifts will frustrate anyone seeking a conventional crime narrative or neat resolution.

More like this (8)
The Tamarind Seed1974
Blake Edwards' elegant Cold War romance with Omar Sharif and Julie Andrews—espionage, forbidden attraction, and moral complications wrapped in a glossy but genuine love story. Deeply underrated.
But The geopolitical intrigue is thin, and some viewers will find it too mannered, too much a product of its decade. The stakes feel smaller than they should.

Cuba1979
Another Redford film, another revolution—this one about an American military officer caught between his job and a former lover as Castro's forces close in. Gritty, unglamorous, and genuinely tense.
But Less character-focused than it intends, and the politics overshadow the emotional core. It never quite decides what it wants to be about.

Reds1981
Warren Beatty's ambitious three-hour romance set against the Russian Revolution, with real witnesses commenting on the events. Epic in ambition, intimate in execution, and genuinely moving about artists caught in history.
But Glacially paced, intellectually dense, and the interwoven documentary segments break romantic momentum. Demands more patience than most viewers have.

The Spy Who Came In from the Cold1965
le Carré's Cold War espionage rendered with unglamorous fidelity and genuine moral complexity. Richard Burton's weary professionalism and the film's commitment to character over spectacle rewards close attention.
But Relentlessly bleak and slow, filmed in drab, wintery locations. If you came for thrills, you'll leave disappointed and somewhat depressed.

The Mission1986
A morally complicated romance (of sorts) amid colonialism and faith in eighteenth-century South America. Jeremy Irons and Robert De Niro, Ennio Morricone's score, and genuine heartbreak about the cost of idealism.
But Heavy-handed at moments, the romance is spiritual rather than passionate, and the tragic inevitability can feel manipulative if you resist it.

Rollover1981
Jane Fonda and Kris Kristofferson in a Pakula thriller about financial espionage and attraction during economic crisis. Intelligent, paranoid, and genuinely weird in ways that reveal more on rewatching.
But The plot becomes genuinely convoluted, and the romance feels bolted on. It's fractured in ways that work thematically but not always narratively.

A Prophet2009
A gambler and a prisoner both navigate systems designed to corrupt them, each making small choices that reveal larger truths about power, survival, and complicity. Both are studies in how individual agency dissolves.
Jacques Audiard's French prison epic following a 19-year-old's transformation over years inside. Spare, brutal, hypnotic cinematography and a protagonist whose moral arc mirrors the film's unflinching political consciousness.
But Two and a half hours in a prison, in French, with minimal sentimentality and violence that doesn't flinch. The pacing assumes you're willing to sit with discomfort.

The Dreamers2003
Both are tales of seduction by a forbidden world—in one case Havana's dangerous glamour, in the other the intoxication of cinema and revolutionary politics. Both romanticize worlds that are simultaneously dangerous and doomed.
Bernardo Bertolucci's sensual, intellectually alive film about two cinephile siblings and an American student during 1968 Paris. Cinema-mad, erotically charged, and deeply romantic about film itself. Bathed in golden light and literary allusion.
But Explicit sexuality, a frankly incestuous dynamic, and an almost oppressive nostalgia for a time and place. If you resist the film's self-consciousness about its own beauty, it will feel precious rather than profound.

People
Cast
Robert RedfordJack Weil
Lena OlinBobby Duran
Alan ArkinJoe Volpi
Tomas MilianMenocal
Daniel DavisMarion Chigwell
Tony PlanaJulio Ramos
Betsy BrantleyDiane
Lise CutterPatty
Richard FarnsworthProfessor
Mark RydellMeyer Lansky
Vasek SimekWilly- Fred AsparagusBaby Hernandez
Directing
- Sydney PollackDirector
- David TomblinFirst Assistant Director
- Adam SomnerThird Assistant Director
Writing
- David RayfielScreenplay
- Judith RascoeScreenplay
- Judith RascoeStory
Production
- Lynn StalmasterCasting
- Ronald L. SchwaryExecutive Producer
- Robin CitrinLocation Manager
- Richard A. RothProducer
- Sydney PollackProducer