Film

Icahn: The Restless Billionaire

Name: Icahn: The Restless Billionaire
Genre: Documentary
Released: 2022
Cast: Carl Icahn, Bill Gates, Oliver Stone, Andrew Ross Sorkin, Cara Lombardo

Biopic

A portrait of Carl Icahn that doesn't look away from its subject's contradictions. The documentary examines how a Queens kid became a billionaire raider, a man who crusades against inequality while embodying its extremes. Brisk, intelligent, heavy with interviews from Gates and other heavyweights. For anyone fascinated by how money and power actually work.

Should you watch it?

Watch it if you enjoy watching a financier's public image get picked apart, and you like documentaries that let a subject's contradictions stand rather than settling on a tidy verdict.

Skip it if you want a fast, crisp business exposé or a close look at deal mechanics; this is a talking-heads portrait, so the finance stays loose.

What it asks of you: At about 102 minutes it moves at a measured clip, asking you to hold several competing views of one man at once and sit comfortably with ambiguity.

Not sure? Find tonight's pick in a minute.

If you liked this

The Big Short2015

Like Icahn, it's obsessed with how the financial system creates fortunes through others' suffering. Sharp, angry, and brilliantly structured to make you understand the mechanics of greed before you fully process the human cost.

But The stylistic flourishes—fourth-wall breaks, celebrity cameos explaining mortgage bonds—can feel gimmicky if you're in the mood for something graver.

Succession2018

If you want to understand how billionaires actually think—the paranoia, the hunger that money can't satisfy, the way power becomes its own addiction—this is the closest drama gets. Jesse Armstrong writes it like he's been in the room.

But Four seasons is a commitment, and the finale divides people sharply. It's also so well-written it becomes almost sympathetic to monsters, which some find morally uncomfortable.

Barbarians at the Gate1993

A brilliant, funny look at the 1988 RJR Nabisco buyout. Shows how titans of finance convince themselves they're the heroes of their own stories while burning everything down. Henry Kravis and Ross Johnson are cousins to Icahn's mythology.

But It's a TV movie from the nineties, and the aesthetic hasn't aged gracefully. The pacing is slower than modern audiences expect.

Not sure tonight? Get a pick in a minute, starting from Icahn: The Restless Billionaire

The wildcard

Something you would not have found on your own.

The Wolf of Wall Street2013

Both Icahn and Belfort are American mythologies about self-invention and appetite. Icahn claims restraint and principles; Belfort claims nothing. Same DNA, different messaging.

DiCaprio's Jordan Belfort is everything Icahn claims to despise—crude, hedonistic, a pure predator. But the film understands something crucial: this energy, this hunger, is baked into the system. It's the same drive in different packaging, same moral vacuum wearing a better suit.

But It's nearly three hours of watching beautiful people do repellent things. Scorsese makes it exhilarating, which some find morally queasy.

The Founder2016

Michael Keaton is mesmerizing as Ray Kroc, a man who saw opportunity and took it without apology. Like Icahn, he's ruthless, charming, and utterly convinced of his own righteousness. The film captures that particular American pathology beautifully.

But It's ultimately sympathetic to a man who wasn't particularly sympathetic. If you need your protagonists to have a conscience, this will frustrate you.

The Laundromat2019

Soderbergh's wild ride through shell companies, offshore accounts, and the machinery that lets billionaires hide their money. It's chaotic and exasperating by design—a mirror to the system itself. Gary Oldman, Jeffrey Wright, and Matthieu Amalric are unforgettable.

But It's deliberately fragmented and sometimes confusing. The anger can feel scattered, and you might leave knowing you've been shown something without fully understanding what.

The China Hustle2018

A taut documentary about how American investors got fleeced by Chinese reverse-merger stocks. Shows the other side of the confidence game—how even smart money can be fooled by the right story and enough charisma.

But It's narrower in scope than Icahn, focused on a specific hustle rather than a lifetime of them. Might feel like a footnote rather than a complete portrait.

Margin Call2011

A single night during the 2008 financial collapse, told with surgical precision. Everyone here is smart, everyone is trapped, and everyone knows the system is rotten. It captures the thought process of men like Icahn—the calculations, the rationalizations.

But It's glacially paced and full of finance jargon. If you want action or emotional catharsis, you won't find it here.

Becoming Warren Buffett2017

A gentler but equally probing look at another self-made billionaire who also claims to believe in restraint and fairness. Useful counterpoint to Icahn—two different philosophies, same outcome, similar contradictions.

But It's softer and more reverent than you might want. Buffett's narrative is largely unchallenged, which makes it less interesting than Icahn's fractured portrait.

A Prophet2009

Both are about self-made men operating by their own code within systems that reward ruthlessness. Both show the psychic cost of that choice, even when you win.

A French prison drama about a kid who rises through brutal cunning and intelligence. It has nothing to do with finance, but it's about the same thing Icahn embodies: how hunger and isolation breed genius, how power becomes addictive, how you can't go home once you've tasted it.

But It's violent, grim, and in French. The world is claustrophobic and there's no redemption waiting. It takes itself and its darkness seriously.

Synecdoche, New York2008

Icahn the documentary is about a man who built and rebuilt himself across decades. Kaufman suggests that project is itself a kind of madness—beautiful and terrible and ultimately hollow. It's the nightmare inside Icahn's dream.

A philosophical nightmare about ambition, creation, and the impossibility of ever being satisfied or understood. Philip Seymour Hoffman's director builds a world to escape his actual life and discovers he's built the same prison. It's about the fundamental emptiness at the heart of self-invention.

But It's baroque, difficult, and deliberately disorienting. Kaufman doesn't explain himself. You either surrender to the fever dream or you resist it the whole way.