In his seventh appearance on the show, the president said he's proud of the work he's done during his time in office but added that there's still "a bunch of other things we want to get done."
"You're always going to fall short, because if you're hitting your marks, that means you didn't set them high enough," said Obama, who still has a year and a half left in the White House. "We don't score a touchdown every time, but we move the ball forward."
Like the rest of the world, Obama is not happy about Stewart's departure from The Daily Show. "I can't believe you're leaving before me," he told the late-night host. "In fact, I'm issuing a new executive order that Jon Stewart cannot leave the show."
Jokes aside, a true-to-form Stewart grilled Obama on heavy issues, including his nuclear deal with Iran, which has drawn ire from Republicans as well as some Democrats.
"I do think the work we did early starts bearing fruit later," the president said. "It just so happens that people are seeing the work we did when we first came in – Iran, for example, it took four or five years to get them to to table."
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This isn't the first time the president has discussed weighty issues on The Daily Show.
Obama – who has appeared on the late-night political satire show now three times during his presidency and four times before he was elected – has touched on topics such as health care, financial reform, and economic recovery during past appearances.
In a 2012 interview, Stewart pressed Obama on everything from Benghazi to "government overreaching" to the president's poor performance in the first presidential debate that year.
"If you look back at 2012 and the series of interviews the sitting president of the United States gave, probably the toughest interview he had was with Jon Stewart," Obama press secretary Jay Carney said in a 2014 interview, according to EW. "Probably the most substantive, challenging interview Barack Obama had in the election year was with the anchor of The Daily Show."
Obama did, however, manage to squeeze in a few jokes during his final Daily Show appearance before Stewart leaves next month – including one about controversial presidential candidate Donald Trump.
"I'm sure the Republicans are enjoying Mr. Trump's current dominance as the front-runner," Obama said.
"Anything that makes them look less crazy," Stewart shot back.