Initially, Jon Stewart didn’t devote much time on the “The Daily Show” to business topics. But then the financial crisis happened, and Stewart, like many others, was drawn to the notion that there was something very wrong with Wall Street. He didn’t always get it right. Fortune’s Dan Primack characterized a segment The Daily Show did on a questionable deal struck by private equity firm Blackstone as too simplistic and unfair. Stewart was roundly criticized for a piece he did on the trillion dollar coin, a hypothetical Washington workaround to the debt ceiling, which was itself a Washington created problem. Among those who called out Stewart was Nobel laureate economist Paul Krugman.
But what Stewart did get right, again and again, and in ways that were more compelling, and certainly funnier than others, is that our complicated financial markets don’t always work in the best interests of average investors, borrowers or even the companies that are supposed to tap them to raise the money that can drive innovation.
Here are six of the most memorable business-related guests and segments from Stewart’s run as the host of The Daily Show. Stewart will host his final show on August 6.
1. The Jim Cramer smackdown
This is thought of by many as one of Stewart’s finest moments. Stewart drags former hedge fund manager and CNBC host Jim Cramer over the coals, essentially blaming him for helping to exacerbate the financial crisis, famously saying (seven minutes into the above clip), “I understand you want to make finance entertaining, but it’s not a [expletive] game. And when I watch that, I get, I can’t tell you how angry that makes me.” Cramer did his best to defend himself, but Stewart clearly came out of the exchange on top.
2. Tim Geithner talks “Stress Test”
The former Treasury Secretary of the United States came on last year to talk about his book “Stress Test,” and he stayed on for more than 40 minutes, most of which was available only online. Geithner defends the bank bailouts, even as Stewart makes some clever jokes. “That first obligation in a panic is to do whatever it takes to protect [the American people] from what we saw in the Great Depression,” Geithner said.
To see the full Daily Show segment, click here.
3. Stewart and Samantha Bee take on Blackstone
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In 2013, Stewart talked about a shady, but legal, insurance deal the hedge fund Blackstone, which he referred to as “an evil wizard’s castle,” did with Spanish gambling company Codere. He then brings on veteran reporter Samantha Bee to figure out why news media wasn’t covering the story more. Perhaps because the deal wasn’t as evil as Stewart seems to think. Shortly after the piece aired Dan Primack got Blackstone’s side of the story. The full story is that the Codere deal was more complicated than Blackstone simply taking advantage of other investors in a troubled company. That doesn’t stop Bee from summing up the deal as “rich assholes want all the money for themselves” and riding a wrecking ball, Miley Cyrus-style.
To see the full Daily Show segment, click here.
4. Stewart trips on the trillion dollar coin
Jon Stewart has a knack for rooting the absurdities in our political and policy debates. But when he made fun of the proposal to mint a trillion dollar coin as a means of obviating the debt ceiling, economist Paul Krugman took umbrage, arguing that the debt ceiling itself is the truly silly idea.
5. Warren Buffett and Carol Loomis appear
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The Oracle of Omaha and his unofficial writer — longtime friend and Fortune writer of nearly 60 years Carol Loomis — appeared to talk about a new book collecting Buffett’s thoughts from the past 40 years. The three also talked about income inequality and the proposed “Buffett Rule,” which Stewart cheekily compared to Lou Gherig’s disease.
To see the full Daily Show segment, click here.
6. Howard Schultz of Starbucks comes on
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In 2014, Stewart talked to Howard Schultz of Starbucks right after the CEO announced that his company would be providing access to a free college education for all of its employees. Stewart asked why more companies don’t do things like this. “Corporations are people, we’ve learned,” Stewart said to chuckles. “But generally they’re sociopaths.” Schultz had been on the show before, but this interview really got to the core of how corporations navigate the struggle of building value for shareholders and providing a good life for their employees.
To see the full Daily Show segment, click here.
For more: TIME: Watch Jon Stewart’s 11 best Daily Show takedowns
