Obama's Last Laugh

Jon Stewart warmed up for his Washington rally this weekend by needling the president on the Daily Show. Howard Kurtz on how Obama did—and whether the comic will incite liberals on the mall, or just joke around.

10.28.10 12:50 AM ET

Jon Stewart warmed up for his Washington rally this weekend by needling the president on the Daily Show. Howard Kurtz on how Obama did—and whether the comic will incite liberals on the mall, or just joke around. Plus, midterm predictions from the Election Oracle.

Jon Stewart didn't just go for the gags.

While joshing around with Barack Obama last night on a set festooned with faux Roman columns, Stewart spoke as the voice of disenchanted liberalism, demanding to know: What happened to that hope-and-change guy?

"You ran with such, if I may, audacity… yet legislatively it has felt timid at times," the host said. "I am not even sure at times what you want out of a health care bill."

The guest, buoyed by an adoring audience, pushed back: "Jon, I love your show"—here Stewart mugged for the camera—"but this is something where I have a profound disagreement with you…This notion that health care was timid—you've got 30 million people that will have health insurance because of this."

That the president of the United States would appear on the Daily Show six days before a midterm election that could sink his party speaks volumes, or at least chapters, about that buzzworthy forum. But it was also a test of sorts for the host, who is casting his big "sanity" rally in Washington as an escape from the nuttiness fostered by the extremes of both parties.

Can Saturday's extravaganza live up to its nonpartisan billing if its ringmaster is seen as too friendly with the Democrat-in-chief? I'd say Stewart passed the initial exam, making Obama feel comfortable while also delivering the zinger that "Democrats this year seem to be running on 'please baby one more chance.'"

Stewart told me years ago that he regarded the nightly interview segment as little more than filler that spared his staff from having to write one more comedy sketch. But it's evolved into an key component of the program, as anyone who saw his combative sessions with CNBC's Jim Cramer or health care critic Betsy McCaughey can attest (though Stewart conceded that Bush torture defender John Yoo "slipped through my fingers").

Obama stepped in it by echoing W.'s praise for Brownie, saying Larry Summers had done "a heck of a job."

"You don't want to use that phrase, dude," Stewart shot back.

Obama's last appearance—days before the 2008 election—was a friendly encounter. Stewart asked whether his "white half" would have trouble making a decision in the voting booth, and the candidate played along, saying he'd been "going through therapy to make sure that I vote properly."

Now Stewart's stature is such that White House spokesman Robert Gibbs was questioned about the rally at a briefing Tuesday.

Q. Robert, does the president not have any concern about the conflation of entertainment comedy and politics? Does that—does it take away from the seriousness?

MR. GIBBS: Jon Stewart is sort of past that.

White House Goes Into Election Bunker ModeEveryone knows Stewart is a liberal. He announced that he was voting for John Kerry (who also stopped by the Daily Show in the waning days of his campaign) and was relentless in attacking George W. Bush for his "Mess O' Potamia" misadventure. But when Obama began to stumble in office, Stewart started taking potshots—such as when the president unwisely set up a teleprompter in a sixth-grade classroom. No national leader remains immune from comedic barbs.

And the left didn't like it: Americablog's John Aravosis accused Stewart of "picking on Dems for insignificant BS to burnish his indie credentials."

There's been some teeth-gnashing in the punditocracy over whether Stewart is stepping out of his funnyman role by orchestrating this rally, as if that were a federal offense. His rally ally, Stephen Colbert, drew similar criticism when he recently testified at a House immigration hearing.

"I think the arrogance of Stewart and Colbert has reached a point with this rally that I find appalling," writes Baltimore Sun television critic David Zurawik. "But I am even more worried about the bow-down-and-blindly-worship followers who seem to have lost all sense of perspective."

C'mon, they're not exactly grabbing pitchforks and forming a third party. But fears that the rally might be seen as (gasp) political prompted National Public Radio to ban its journalists from attending. One wag wondered whether it would be acceptable to attend but not laugh.

The gathering on the Mall, featuring such performers as Sheryl Crow, captures the dual sides of the Stewart persona. There is the just-a-standup-comic dude who says he's happy to deliver social commentary but don't take him too seriously because he's all about the punchline. Then there's the razor-sharp political analyst and media critic who cares passionately about the issues he dissects under the cloak of mockery.

I learned this when I was on the Daily Show and Stewart got so wound up ripping the media that he went way past our allotted six minutes, whispering to me, "Don't worry, we'll cut this part out." The man fervently believes that news outlets fail to get at the "truth" because they are superficial, sensational and obsessed with phony balance. It's no accident that his famous rant on Crossfire, accusing the hosts of "partisan hackery," got CNN to cancel the show.

Colbert once told me that reporters would privately confide to him, "I wish I could say what you say." Well, he asked, why couldn't they? If a politician denied saying X, and there was tape of him saying X, why couldn't news programs play the video and bust the guy, the way Comedy Central did?

Some MSM types now mimic the masters. But if the fake-news style has infiltrated the mainstream, is the Rally to Restore Sanity a meta-sendup of Glenn Beck's religious revival at the Lincoln Memorial? Stewart says no, that it's for "the people that are too busy, that have jobs and lives, and are tired of their reflection in the media as being a divided country and a country that's ideological and conflicted and fighting," as he told Larry King.

Surely it's not his problem that some Democratic strategists say the rally could give the liberal side a morale boost, or that Arianna Huffington is spending about $250,000 on bus service to the event. The man says he's all about the mushy middle.

Some of the advance criticism seems to emanate from the humor-impaired, the same people who found it blasphemous for Brian Williams to host Saturday Night Live. It's as if they have to squeeze Stewart into a box, that he can't be both satirist and citizen, that he should have stayed on his side of the camera. But he demonstrated Wednesday night that he can press a president without shelving the shtick.

When Obama began, "Let me say this about members of Congress," Stewart jumped in: "Are you gonna curse?" But that jibe followed a question about backpedaling Democratic candidates and whether the president had "convinced your own party that the legislative progress has been enough."

Obama mentioned three Democratic House members who he said had taken tough votes to support his policies. It's worth noting that all of them—Tom Periello in Virginia, Betsy Markey in Colorado and John Boccieri in Ohio—are trailing their Republican challengers by a few percentage points in recent polls. Perhaps the president was giving them a calculated shout-out.

Stewart wasn't afraid to wander into the weeds on health care. And when he questioned the hiring of Larry Summers, Obama stepped in it by echoing W.'s praise for Brownie, saying the economist had done "a heck of a job."

"You don't want to use that phrase, dude," Stewart shot back.

That, of course, took place within the confines of a Washington studio. By what standard, then, should we judge the Stewart stagecraft on Saturday?

Certainly not by the crowd size, or whether the host is better than he was at the Oscars. If the rally is merely entertaining, he will have failed to make a larger point. If the rally is excessively political, he will have sacrificed a bit of his comedic credibility in favor of earnest activism.

Or Jon Stewart could hit the sweet spot between being provocative and preposterous. And that would be a truly sane outcome.

Howard Kurtz is The Daily Beast's Washington bureau chief. He also hosts CNN's weekly media program "Reliable Sources," Sundays at 11 am ET. The longtime media reporter and columnist for The Washington Post, Kurtz is the author of five books.