Jon Stewart has never been shy about calling out dysfunction in the system. In a 2024 episode of the “2 Bears 1 Cave” podcast with Tom Segura, the “The Daily Show” host, broke down why so many middle-class Americans feel squeezed—even when they do everything “right.”
A Cycle That Doesn’t Add Up
“Most people, I think in the general area of what you would consider middle class…are stuck in this weird trap,” Stewart said. “Which is: I work till I’m 40 or 50 till my kids are going to college. Now I’m paying for their college. But just at that moment, my parents are getting sick.”
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The result, he explained, is a generation stuck in both directions. Parents who saved for decades watch their savings evaporate from medical bills and tuition costs—simultaneously. “Now I’m in debt on the college for the kids while also maybe going into a little bit of a debt for the parent,” Stewart said. “So now everything that you built up, all that equity right over those 20 years of work, is gone.”
The conversation was wide-ranging, touching on politics, fatherhood, health care, and the frustrations of trying to fix anything through normal channels.
System Rigged, Solutions Missing
Stewart argued that the system isn’t broken by accident. It’s designed to funnel public funds to corporate middlemen. “There shouldn’t be food insecurity in a country as rich as this,” he said. But even with programs like food stamps, most of the benefits end up with big food conglomerates because of what people are forced to buy: ultra-processed, unhealthy food that sets off a chain reaction.
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“So what do they do? They give us all diabetes,” he said. “Then what’s the next step? Big Pharma comes in.”
Even popular legislation like the Affordable Care Act, Stewart pointed out, was largely a giveaway to insurance companies. “How about we just give you a ton of money and, with that ton of money, you’ll cover people that maybe you wouldn’t normally cover,” he said.
The Problem Isn’t Resources, But Priorities
Stewart also talked about bloated corporate profits and endless healthcare middlemen. “I’m not saying you don’t want to have private corporations and private property and innovation and all those different things. But do we have to subsidize it?” he said.
He explained that what Americans really need is targeted support that matches real life: affordable education, child care and elder care. “Something that connects to your life,” he said. “It feels like we live in a place where that seems like it should be possible to do,” Segura added.
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One Bright Spot: Cuban’s Pharmacy
Stewart praised billionaire Mark Cuban for launching a fair-priced pharmaceutical company called Cost Plus Drugs to combat predatory drug pricing. “That can be done everywhere,” he said. “They put old people on buses to Mexico to get like insulin.”
The comedian-turned-activist said he’s seen firsthand how hard it is to get lawmakers to do the right thing. While lobbying for the Sergeant First Class Heath Robinson Honoring our Promise to Address Comprehensive Toxics Act of 2022—a bill to help veterans exposed to toxic burn pits—he said members of Congress told him, “Could you guys write the legislation?” Stewart recalled, “I could write a 10-minute bit about the legislation, but I don’t know the first thing about [actually drafting it].”
The system, he said, is built for insiders, not regular people. “They get ensconced in this really protected system and they lose sight of the people that they’re supposedly there to represent.”
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