President Obama first visited "The Daily Show With Jon Stewart" in November 2005 when he was a rising star in the Senate who'd made a name for himself with a stirring speech at the 2004 Democratic National Convention.
Nearly a decade and many gray hairs later, both men are preparing to leave office. Obama has 18 months to go before his successor moves into the Oval Office, while Stewart signs off after 16 years at "The Daily Show" next month -- a fact that many, including Obama, are already mourning.
"I can't believe that you're leaving before me," he said Tuesday, prompting enthusiastic applause from the audience when he proposed "issuing a new executive order that Jon Stewart cannot leave the show."
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"To me, this is a states' rights issue," Stewart joked in response.
While both men's admiration for each other was evident, their conversation was not exclusively a love fest. Stewart held Obama's feet to the fire over one of his most passionate causes, the administrative delays that have left many veterans waiting months for medical treatment at government-run health facilities, while Obama needled Stewart for jumping, along with much of the media, on the alleged IRS scandal.
Here's what the president had to say on these issues, and several others, Tuesday night in the televised interview and an extended conversation made available online.
On improving the Department of Veterans Affairs:
"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."
"I can say this unequivocally: The VA is better now than when I came into office. Government works better than when I came into office. The economy by every metric is better than when I came into office. And so the reason I can sleep at night is I say to myself: 'You know what? It's better.' Now am I satisfied with it? No. And should voters be satisfied with it? Absolutely not. Because otherwise we get complacent and lazy and stuff doesn't happen."
On hitting a winning streak in the waning days of his presidency:
"A lot of the work that we did early starts bearing fruit later. And it just so happened over the last couple months that people are seeing some of the work that we started way back when I first came in.... The way I'm feeling right now is I've got 18 months. There are a bunch of other things that we want to get done. Climate change is a good example."
On critics of his nuclear deal with Iran:
"You've got to ask them: 'Well, what represents a better deal? What is it that you think could happen?' Typically they're vague and they fall back on, 'Well, if you beat your chest a little bit more or brought Dick Cheney to the negotiations, everything would be fine.'"
On the partisan media landscape:
"I think that the problem with our interaction with the media is probably overstated. I think what's understated is the Balkanization, the splintering of the media so it's hard for us to get one conversation. You have folks who are constantly looking for facts that reinforce their point of view as opposed to having a common conversation. One of the things we have to think about, not just the president but all of us, is how do we join together in a common conversation around something other than the Super Bowl."
On the IRS:
"Congress had passed a crummy law that didn't give people guidance in terms of what they're trying to do. They did it poorly and stupidly.... The truth of the matter is there was not some big conspiracy.... The real scandal around the IRS right now is that has been so poorly funded that they can't go after these folks who are deliberately avoiding tax payments and the real scandal is a tax code where multinationals can pay zero taxes making massive profits."
On the current frontrunner for the GOP nomination in 2016:
"I'm sure the Republicans are enjoying Mr. Trump's dominance."
Follow @MeredithBlake on Twitter.
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