Film
Operation Odessa
Operation Odessa is a documentary thriller about three misfits—a Russian mobster, a Miami hustler, and a Cuban spy—who attempted to sell a Soviet submarine to Colombian drug lords in the early 1990s. It's a breathless, darkly funny true-crime story that feels too wild to be real. Perfect for anyone who loves crime stories where the absurdity is as gripping as the danger.
Should you watch it?
Watch it if you enjoy true-crime stories that sound made up, where the pleasure is watching real people talk about their own absurd schemes with a straight face and a lot of pride.
Skip it if you want a tight, polished documentary with a clear arc, since this one leans on talking heads and wanders through the scheme's odd byways at its own unhurried pace.
What it asks of you: Ninety-two minutes of interviews and archive-style storytelling, so it rewards patience and a willingness to follow a tangled plot without much visual flourish.
Not sure? Find tonight's pick in a minute.
If you liked this
Catch Me If You Can2002
A stylish cat-and-mouse tale about a charming con artist and the FBI agent hunting him. Like Odessa, it finds comedy and humanity in criminals who are more clever than dangerous, with charismatic leads you can't look away from.
But Spielberg's direction occasionally softens the stakes. If you want real consequences, not just a game, this might feel too breezy.
The Wolf of Wall Street2013
Excess, swagger, and barely-believable true crime told with operatic energy. Both films find dark humour in men so caught up in the game they lose sight of the danger they've created around them.
But Nearly three and a half hours of relentless debauchery. Some find it numbing rather than thrilling; others just find it exhausting.
McMafia2018
A glossy, propulsive thriller about organized crime that moves between continents with the same feverish energy as Odessa. It's got that same sense of criminal networks as baroque chess games played by charismatic idiots.
But The plot can feel scattered across eight episodes. If you want tighter storytelling, the TV format works against it here.
Not sure tonight? Get a pick in a minute, starting from Operation Odessa
The wildcard
Something you would not have found on your own.
Lord of War2005
Both centre on men operating in the margins between superpowers, selling weapons in a world where legality is a fiction negotiated between governments. Both suggest the criminal and the state are playing the same game.
Nicolas Cage as an arms dealer navigating geopolitics, bureaucracy, and absurdity with charm and desperation. It shares Odessa's fascination with how international crime works—the logistics, the contacts, the moment when the game stops being theoretical.
But It's a political thriller dressed as character study. Some find it preachy; others find the tonal shifts between satire and despair uneven.
More like this (7)
Blow2001
Johnny Depp in a cocaine epic that captures the intoxicating rush of the drug trade in the '80s and '90s. Both films centre on men seduced by the scale of what they're attempting rather than its logic.
But It's visually stylish to the point of glamorizing addiction and criminality. The film never quite lands its moral reckoning.
The Godfather Part II1974
The definitive crime epic that established the genre. Odessa is fundamentally a smaller, funnier, more documentary take on the same world of transnational criminal ambition and the corrosion of character.
But It's nearly three and a half hours and moves at a deliberate pace. Modern viewers sometimes find the pacing glacial compared to current thrillers.
City of God2002
A Brazilian crime film with kinetic energy and dark wit. Like Odessa, it captures the ecosystem of organized crime with visual flair and finds unexpected humanity in criminals operating at different scales.
But The violence is visceral and sometimes exploitative. The documentary-like style can make brutality feel matter-of-fact rather than shocking.
American Hustle2013
A con-artist thriller that prioritizes style, charm, and the psychology of the grift. Both films are fascinated by men who talk themselves into impossible situations and somehow almost pull them off.
But The plot is deliberately meandering and the ending feels slight. If you want tight narrative resolution, this resists it.
Ozark2017
A crime family saga that captures the steady escalation of criminal entanglement. Odessa's one-shot audacity is inverted here—same world, but watched over seasons as compromise compounds into catastrophe.
But Four seasons is a long commitment and quality dips by the end. The protagonist's moral arc gets muddled by sheer repetition.
The Two Popes2019
A dialogue-driven drama about two men from opposing worlds finding unexpected common ground. Like Odessa, it's built on the chemistry between charismatic characters and finds humour in high-stakes situations where stakes feel negotiable.
But It's talky and meditative rather than thrilling. If you're seeking propulsion, this moves at a contemplative pace.
American Animals2018
Both blur documentary and dramatization, letting subjects tell their own story while showing you the story unfold. Both are fascinated by the moment ambition collides with reality and the gap between the two.
A heist film that blends documentary interviews with dramatic reconstruction. Four college kids steal rare books; the film cuts between them now, reflecting on their younger selves committing the crime. It captures the same dreamlike unreality as Odessa—the gap between what people planned and what actually happened.
But It's formally experimental in ways that distract from narrative momentum. The crime itself is small-scale, which some find anticlimactic.
People
Cast
- Ludwig FainbergSelf
- Kristy GaleotaSelf
- Tony GaleotaSelf
- Brent EatonSelf
- Mike McShaneSelf
- Dick GregorieSelf
Directing
- Tiller RussellDirector
Production
- James CarrollCo-Producer
- Justine MedeirosCo-Producer
- Trevor DavidoskiConsulting Producer
- Aaron SaidmanProducer
- Eli HolzmanProducer
- Sheldon YellenProducer
- Maria RachkoProduction Manager
- Kim FoehringerResearcher