In his deeply personal and politically charged documentary, filmmaker Justin Schein ventures into emotionally turbulent territory by turning the camera on a subject he knows better than most—his own father. A seasoned documentarian known for grappling with emotionally dense topics such as 9/11 and childhood depression, Schein now aims his lens at a more intimate yet equally complex figure: Harvey Schein, a man of considerable wealth and even more considerable opinions.
The film opens on idyllic imagery: a placid lake, autumn foliage ablaze in color, and an imposing Connecticut estate—the so-called “Country House.” It’s 2003, and what could be a commercial for American prosperity quickly pivots into a portrait of its contradictions. This peaceful scene gives way to Harvey Schein, a man both formidable and fixated, sounding off about his least favorite subject: the U.S. estate tax, which he calls a form of legalized robbery.
“My dad’s favorite topic,” Justin narrates, “is how to make sure the government doesn’t get a penny when he dies.”
Harvey Schein doesn’t just dislike the estate tax—he is almost pathologically obsessed with it. What others might see as a fair share, Harvey interprets as a betrayal of personal freedom, the state’s intrusion on a life of industrious financial accumulation. His passion borders on a kind of madness, or at least eccentricity. But as the film progresses, his son peels back the layers to uncover the deeper motivations—and contradictions—that fuel this relentless crusade.
The estate tax, or as conservatives have successfully rebranded it, the “death tax,” looms large over the elder Schein’s life. But as Justin dryly points out in the voiceover, this is not a concern for most Americans. The exemption threshold is so high—$27 million at the time of filming—that very few people are affected. Which begs the question Justin scribbles in his notebook early in the film, and one that many viewers might share: “Why am I watching this movie?”
The answer lies in the collision between the personal and the political. This isn’t just a documentary about estate planning or conservative economics. It’s about how ideology takes root in families, how wealth can distort relationships, and how even love can be taxed—if not by law, then by resentment and misunderstanding.
A Family Affair with a Political Edge
The film toggles deftly between intimate family scenes and broader social commentary. Justin pits his liberal sensibilities—what he openly admits might be “bleeding-heart” tendencies—against his father’s cold, pragmatic worldview. These clashes are not just philosophical. They are deeply emotional, revealing the generational and ideological divides that fracture many American households.
In one of the film’s many telling moments, Harvey reflects, “It’s not a bad problem to have, as long as you don’t let it drive you crazy.” But as the footage unspools, it’s clear that this is precisely what has happened. Harvey is driven—not by greed, exactly, but by a deep-seated anxiety that his life’s work will be undone by governmental interference. His vision of fairness is not communal, but familial. Why should strangers benefit from what he’s earned for his children?
Yet, ironically, this obsession with legacy and wealth often alienates the very people he seeks to protect.
The Voices We Hear—And the Ones We Don’t
To his credit, Justin doesn’t stack the deck entirely against his father. He assembles a chorus of voices from across the ideological spectrum to weigh in on taxation, inequality, and the American dream. Among them is former U.S. Labor Secretary Robert Reich, a frequent voice in progressive circles, who articulates the growing economic disparity in the country. Reich’s presence gives the film a grounding in policy, adding weight to Justin’s arguments without making them feel preachy.
Then there’s Clive Davis, legendary music executive, who recalls Harvey Schein’s own time as a hard-nosed record industry player. Harvey’s reputation, Davis suggests, was built more on his business instincts than his musical taste—a man always watching the bottom line. In fact, Harvey was such a force in the industry that Sony’s co-founder Akio Morita took him to Japan for a stint. There, he became a passionate supporter of the Betamax format—a superior technology to VHS, as any old-school electronics journalist will affirm. Yet, as history shows, even the better product can lose out to the market’s whims.
The film is peppered with these kinds of detours—into history, memory, and pop culture—that give it texture and levity. For instance, Schein includes a tongue-in-cheek Godzilla clip to depict one of his father’s verbal tirades, describing Harvey as turning into a “fire-breathing monster” whenever the estate tax is mentioned. It’s a literal-minded choice, but one that speaks to the emotional intensity of these family discussions.
The Luxury of Frugality
Interestingly, despite his wealth, Harvey is a man of modest habits. He champions walking over public transport, and public transport over taxis. He lives by a frugal ethos that’s as much philosophical as it is economical. In a more generous light, you could see this as a kind of humility—proof that he doesn’t worship money for its own sake. But Justin sees through the contradiction. His father benefited from government programs like the G.I. Bill—programs that were systematically denied to Black veterans—and yet rails against redistributive policies that aim to level the playing field.
This raises the ethical paradox that haunts the film: Can a man be held accountable not just for his personal choices, but for participating in a system that privileges him while excluding others? For Justin, the answer seems to be yes, or at least, it’s a question worth confronting. But in doing so, he risks turning his father into a symbol of something larger than himself—a scapegoat for societal ills.
One might argue that Harvey is being saddled with burdens that are not entirely his to bear. After all, as the film makes abundantly clear, his wealth was not inherited but built through relentless work. That doesn’t absolve him of critique, but it complicates the narrative. And perhaps that is Justin’s point: the story of wealth in America is not simple, and neither are the people who embody it.
The Tragedy in Perspective
As the film marches forward, Harvey’s personal life begins to fray. His marriage unravels, and even he seems to sense the futility of his obsessive planning. In one poignant moment, he recalls a conversation with his mother, who spent her life saving for her children only to realize it had become “ridiculous.” Harvey sighs and says, “And now I find myself being ridiculous.”
It’s a rare moment of vulnerability, one that punctures the film’s otherwise steady tempo of confrontation and commentary. Here, the documentary touches something more universal: the fear of death, the desire for legacy, the dread of being forgotten or misrepresented. It’s no longer about taxes or fairness—it’s about meaning.
And in that light, the title “The Tragedy of a Ridiculous Man” (though never explicitly named in the film) feels apt. Harvey Schein is not a villain. He is a man who has spent his life trying to secure a future for his children, only to alienate them in the process. He’s not ridiculous because he’s wrong, but because he can’t see past his own fixation long enough to understand the deeper values at play.
A Movie About Privilege That Acknowledges Its Own
It’s worth noting that the film itself occasionally stumbles under the weight of its subject. For viewers who struggle financially, who rent cramped apartments or juggle multiple jobs, the story of a wealthy man lamenting how to preserve his fortune might feel tone-deaf or indulgent. The filmmaker seems aware of this, offering self-effacing commentary and ironic asides—like a longing reference to the local public pool he wishes he could visit instead of editing footage of tax arguments.
Still, this awareness doesn’t always redeem the film’s more indulgent stretches. At times, you may feel the urge to echo the filmmaker’s own scribbled complaint: “Why am I watching this?” But in the end, the answer circles back to something deeper: because these conversations matter, even when they’re uncomfortable, even when they make us squirm.
Because in documenting the ideological divide between himself and his father, Justin Schein also captures a broader American rift—the gap between generations, between classes, between those who believe government can be a force for good and those who see it as a threat to personal liberty.
Inheriting More Than Wealth
In its final act, the documentary reveals one last twist. Despite his son’s moral objections, Harvey finds a legal maneuver to help his heirs avoid paying the estate tax. It’s a hollow victory, one that might feel like a betrayal—or at least a disappointment—after so many attempts at dialogue. But it’s also oddly fitting. This is, after all, a man who always gets what he wants. That’s part of the tragedy too.
And yet, the film doesn’t end in bitterness. For all its critique, it is, at its core, a love letter. A complicated one, full of frustration and generational dissonance, but a love letter nonetheless. Justin Schein may not agree with his father, but he doesn’t stop trying to understand him. In that effort, there’s grace.
