4 Times Jon Stewart Called Out Obama On 'The Daily Show,' A Level Of Comedic Reporting That No One Else Can Touch

Daily Show host Jon Stewart knows how to conduct a great interview. More importantly, he knows how to conduct an interview with the commander-in-chief of the United States — and that's no easy feat (just ask The Daily Caller's Neil Munro, who once interrupted the president mid-sentence to ask a flippant question about "foreigners"). It takes a light touch and a lot of propriety to address the president without coming off as entitled or rude, but more than that, it takes guts to politely call him out when the American public believes the administration may have slipped up. Tuesday night was no exception. There were plenty of times Stewart called out President Obama, particularly on several tough issues his administration had come across in recent months.

Obama has now made seven separate visits to Stewart and the Daily Show gang over the past eight years (three of them as president), and during all of them, Stewart has maintained a tough air of skepticism, preferring not to handle the president with kid gloves despite his rank and the fact that, as a comedy host, a breezy interview might arguably fare better with viewers.

"You'll find almost unanimous agreement that you've failed," said Stewart during an unaired portion of the interview, calling out the administration's hollow promises of reform among Veterans Administration health services, which came under heavy fire in 2014 for allegedly faulty scheduling procedures and claims of inappropriate record-keeping (the VA's top health official and VA Secretary Eric Shinseki both resigned over those claims).

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Obama responded:

If you have a government that was built on 1930 models and it’s not updated for decades, there’s going to be a gap, relative to what other folks do. ... Government works better now than it ever has, given what we ask it to do. ... [The problem is figuring out how to] systematically work through some of the challenges of a big, freaky bureaucracy.

It was a meager and diplomatic response on the president's part, but a terrifically meaty inquiry by Stewart, who also went on to call out Obama on a few other hot-button issues throughout the interview.

On Iran & The Infamous Nuclear Deal

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Putting the president directly on the defensive regarding the recent (and heavily criticized) nuclear deal struck with Iran, Stewart quipped, "Whose team are we on in the Middle East?" Obama attempted to intervene on Stewart's apparent comedic trajectory by explaining that his query wasn't "quite right," when Stewart interrupted:

Who are we bombing?

Obama then joked that "if [the administration] had brought Dick Cheney to the negotiations, everything would be fine."

On Why He Can't Get Stuff Done

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As Obama began to launch into his sentiments regarding the current status of Middle Eastern conflict, Stewart interrupted him quickly to cut to a commercial break, leaving this zinger on the constant political stalemate in Washington and the president's failed attempts at getting things done:

What you said about the Iran pact was excellent. And once the Senate shoots it down, we'll talk about it again.

(Sorry, Mr. President, we laughed a little too hard at that one.)

On The Media

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Of course, no Daily Show episode would be complete without a veiled barb at the fine folks at Fox News and a comment on White House journalism. In a sarcastic tone, Stewart asked the president whether the media was asking too much in its hard-hitting press inquiries or if they were impeding on his seemingly "guarded" demeanor:

Are the media — myself included — are we focused on the wrong things? Are we demanding too much of you? Are we demanding to much of the government?

The president responded that, while some media "got on his nerves ... more than others," he had done everything in his power to make himself open to them. Speaking on the recent, one-hour Iran deal news conference, Obama noted:

Not only did I stay there for an hour, I said, "Who else has got a question?”

Stewart shot back:

On your terms, though. You feel really good about that deal. If you didn't feel as good about that deal...

Obama then conceded:

I think the truth of the matter is, there have been a lot of times I sat there, and we talked about stuff where I did not feel as good about what happened, but I feel that we have to be accountable.

On "Shared Purpose"

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In a smart move, Stewart made sure not to forget Millennials during Tuesday's interview, asking the president whether he believed there was a way to counter feelings of distrust among more youthful generations and exhaustion of service members' families who might have grown weary with the current bureaucratic haze in the White House and on Capitol Hill. Stewart stated:

We have all these endless wars — it's been 15 years. We're in Iraq, Afghanistan, Yemen. Military families, [who make up] less than 1 percent of Americans, are bearing the entire brunt of this. There is no sense of shared sacrifice.

Obama then responded that the way to stem the tide of pessimism was to get Americans involved in their communities and with local governments, citing his own time as a community organizer as a possible example:

This notion that young people have lost their idealism, or that they're too cynical or ironic, it's not true. But we have to give them pathways to get them involved.

We have this huge issue of war and peace. ... You've got a bunch of talking heads and pundits, and folks who are not going to be making sacrifices if, in fact, you end up in a conflict, who are reprising some of the same positions that we saw during the Iraq war, not asking tough questions. And if they're not hearing from citizens, then we end up making bad choices.

The president then added that "if people are engaged, eventually the political system responds," despite money and lobbyists.

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