When Barack Obama met Jon Stewart: A love story

President Obama talks with Jon Stewart, host of "The Daily Show," during Tuesday's taping in New York. It is Obama's third appearance on the show as president and seventh appearance overall.

President Obama talks with Jon Stewart, host of “The Daily Show,” during Tuesday’s taping in New York. It is Obama’s third appearance on the show as president and seventh appearance overall.

(Evan Vucci / AP)

Rewatching President Obama’s appearances on “The Daily Show With Jon Stewart” is like watching a love story unfold, with the initial meet-cute, the excitement of the initial courtship and the snipes that come after the honeymoon period wears off and the relationship reaches a comfortable security. Obama will make his final appearance on Stewart’s show tonight.

The meet-cute: Sen. Obama makes his first appearance on the show

Obama starts off young, jubilant and idealistic in his first interview with the liberal Stewart on Nov. 7, 2005. He’s the freshman senator from Illinois still riding a wave of hype after his powerful keynote at the 2004 Democratic National Convention.

In typical Stewart fashion, the interview touches on healthcare, Senate hazing and Iraq but not on the book Obama was there to shill: “Dreams From My Father.”


Obama is still learning the ropes — instead of coming to Stewart’s New York studio, he appears via satellite because he wanted to stay in Washington, D.C., and vote on what his staff thought was a defense bill but turned out to be a healthcare bill — and he responds jovially when Stewart asks about hazing in the Senate.

“They make me sharpen pencils, and sometimes I have to stand between Harry Reid and Bill Frist,” Obama says, referring to the minority and majority leaders.

Obama is enough of a newbie to tell Stewart that appearing on the show gave him “coolness” with his wife and 4-year-old daughter, who knew Stewart from “Elmopalooza.”

But Obama is already sensing more is in store for him.

“I worry about the hype,” he says to Stewart. “The only person more over-hyped than me is you.”

Here’s the full segment:

The Daily Show
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The initial courtship: Obama hits the ‘Daily Show’ on the campaign trail

Two years after their meet-cute, Stewart welcomes Obama back to the show as a presidential candidate.

Obama makes two appearances while fighting his way through the Democratic primaries against Hillary Rodham Clinton, first on Aug. 22, 2007, and again April 21, 2008. Stewart has Clinton’s husband, former President Bill Clinton, on the show before the primaries heat up but not the candidate herself. Obama appears again Oct. 29, 2008, after he has secured the nomination and just days before the election.

In the three interviews with Obama, Stewart throws softballs, mostly about the dominant media narratives in the presidential race.

The first of these dates — er, appearances — is hopeful, with Obama believing he is the one to shake up Washington. The second includes bad omens of a weakening economy and increasing tensions over whether white people will vote for a black president.

Stewart satirizes the situation by asking Obama to tell the truth about whether he’ll enslave the white race if he’s elected.

“That is not our plan, Jon. But I think your paranoia might make you suitable as a debate moderator,” Obama replies.

By the third, once Obama has become the Democratic nominee, Stewart is joking about Obama’s critics calling him a Marxist, a socialist and even a witch.

Obama shares Stewart’s sarcasm at the ridiculousness of the accusations. “I said today that I think they found proof that while I was in kindergarten I shared some toys with my friends, and that is clearly a sign of subversive activity,” he says. “Being on your program, I think, is further evidence of these tendencies.”

Here’s the first of those segments:

The Daily Show
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And links to the rest of them: Aug. 22, 2007, part 2; April 21, 2008, part 1; April 21, 2008, part 2; and Oct. 29, 2008

Honeymoon’s over: Obama makes his first ‘Daily Show’ appearance as president

The courtship between Stewart and Obama that was so clear in the prior appearances has slipped into the testy part of a relationship when the scales fall from one’s eyes and the other person’s flaws become apparent.

Obama’s first “Daily Show” visit as president of the United States is Oct. 27, 2010, when he is staring down the midterm elections. The conversation gets testy in a three-part interview as Obama defends his achievements. Stewart calls his legislation on healthcare “timid” and challenges his praise of Harvard economist Larry Summers, calling the president “dude.” Obama tries not to “lump” Stewart in with other pundits he disagrees with. Stewart tries not to lump Obama in with other presidents.

The honeymoon is clearly over, starting from the moment Obama appears to reject Stewart’s offer of water in a “Mug Force One?” cup. Throughout the nearly 27-minute interview, Obama makes his case for progress, and Stewart expresses his disappointment.

The interview ends with Stewart asking Obama if he will now run as a pragmatist, with a twist on his 2008 rallying cry: “Yes, we can, given certain conditions.”

“I think I would say, ‘Yes, we can, but it is not going to happen overnight,’” Obama replies.

Democrats ended up losing the House in the 2010 midterms as well as six seats in the Senate.

Here’s the first part of that interview:

The Daily Show
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And links to the other segments: Part 2 and Part 3.

A secure relationship: Obama visits while running for reelection

By 2012, when Obama makes his sixth appearance Oct. 18 while running for reelection against Republican nominee Mitt Romney, Stewart gently teases the president about his epic failure in the first debate and gives him free rein to make either the positive case for his own reelection or the negative case. Here, the relationship seems to have fallen into the comfortable joshing and security of an old married couple.

Beyond asking Obama what happened in the debate, the only tough question is over Benghazi.

Romney never appears on Stewart’s show.

Here’s the first part of Obama’s appearance:

The Daily Show
Daily Show Full Episodes, More Daily Show Videos, Comedy Central Full Episodes

And a link to Part 2

Love fest? Obama’s last visit to Stewart’s ‘Daily Show’

Early reports indicate the president’s seventh and final appearance on Stewart’s “Daily Show” is filled with mutual admiration.

“I can’t believe you’re leaving before me,” Obama told Stewart on Tuesday. “I’m going to issue an executive order. Jon Stewart cannot leave the show. It’s being challenged in the courts.”

Stewart replied: “To me, this is a states’ rights issue.”

READ MORE: Obama defends record, begs Jon Stewart to stay at ‘The Daily Show’