Critics worry that Stewart will cross the line between commentator and political participator. | REUTERS Jon Stewart gets serious

Jon Stewart’s “Rally to Restore Sanity” on the Mall Saturday has occasioned handwringing from some devoted fans who worry that he’s losing his outsider credibility, and celebration from some Democrats who hope to channel his energy to advance their electoral prospects.

But Stewart is an entertainer and, just as when Glenn Beck led a rally on the mall, this rally will be all about him and his Comedy Central partner Stephen Colbert.


Their flirtation with political activism carries risks — just as some believe Oprah Winfrey did real damage to her image with a heartfelt endorsement of Barack Obama. But it also carries massive opportunities for Stewart, a man positioning himself as a cultural figure as central to his generation as Johnny Carson was to an earlier, less distracted one.

“It’s fantastic for the brand,” said MSNBC analyst Lawrence O’Donnell, marveling at Stewart’s ability to escape the TV section of the newspaper and generate what’s known as off-the-page publicity. “He’s a great comedian extending his work to another stage.”

“He knows what he does for a living,” O’Donnell said. “He will stand up there as a comedian and leave as a comedian.”

Stewart’s gambit had already proved itself out, perhaps, Wednesday night, when he scored an interview with the president of the United States, whose presence was enough to quiet grumbles from some on the left that an election-eve snark-fest made light of the real dangers of Republican control.

But if he's on trial for sycophancy, Stewart appeared set on proving his independence from Obama and the White House, choosing to advance the critique from the left that Obama — who appeared, at times, chastened — had been too cautious and moderate in advancing and selling his presidency.

“You ran on very high rhetoric, hope and change, and the Democrats this year seem to be running on, ‘Please baby, one more chance,’ ’’ Stewart quipped to Obama, chiding him for – if anything – a presidency too “timid” as Obama used the interview to plead with his supporters to vote.

Stewart repeatedly baited Obama with his own words and his 2008 campaign message.

It's " 'yes we can,' given certain conditions," Stewart said.

" 'Yes we can,' ’’ Obama replied almost resignedly, “but it's not going to happen overnight."

Stewart will navigate two sets of risks Saturday: He will, a handwringing legion of journalists and bloggers worry, cross the once-bright line from commentary to political participation, and find himself stranded, unable to return.

And he could — television industry analysts say — alienate portions of an audience for his show that isn’t as polarized as that of the real cable news shows, with viewers divided starkly left and right.

The first risk has been the subject of a great deal of prose, much of it in The Washington Post, as TBD.com’s Ryan Kearney catalogued Wednesday. Writers suggest either that Stewart is taking politics too seriously or that his supporters aren’t taking it seriously enough, and those fears are shared by some of Stewart’s most devoted aficionados.

“He’s moving to a very new position — and very much runs the risk of alienating some people who liked him because he didn’t seem to be positioning himself as in the mainstream of political life,” said Geoffrey Baym, who actually studies “The Daily Show” at the University of North Carolina-Greensboro. Stewart, he said, is transforming himself from an “outside figure” to a “mainstream political player.

“He’s walking a tightrope here,” Baym said.

A liberal executive who sometimes works with Stewart, and who declined to be quoted by name for fear of jeopardizing the relationship, said Stewart had “gotten in way over his head.”

This executive worried that Stewart wouldn’t have either the political or the comic impact he sought. “It’s one thing doing some stunt or doing some shows from Washington this week,” this person said. “It’s another thing to organize a rally whose goal is muddy at best.”

With Stewart’s goal vague, others are looking to co-opt the energy: Everyone from the Democratic National Committee to campaigners for the legalization of marijuana is organizing political events in tandem with Stewart’s rally.

But Stewart’s schtick has always blended politics and comedy, with a dash of ambiguity about his own role, and he’s given no sign that he’ll break out of character on the Mall.

“What we are doing is we are using the rally format to do the same thing we do with our shows,” Stewart told Larry King recently. “The message will be a very similar-type idea.”

Perhaps the more serious concern is that if Stewart appears to be rallying Democrats for the midterms — as Democrats earnestly hope — he’ll alienate some of his fans. The Pew Research Center in Washington found last month that 41 percent of his fans identify themselves as Democrats, 38 percent independents, and 18 percent Republicans. Twenty-five percent identified themselves as Christian conservatives, and 13 percent as supporters of the tea party movement.

“Keith Olbermann, Rachael Maddow, even The New York Times have substantially more Democratic audience,” said Michael Dimock, Pew’s associate director for research.

Oprah Winfrey clearly risked her apolitical image and some analysts believe she paid a commercial price when she appeared at rallies with Obama on the cusp of the 2008 Iowa caucuses. She became embroiled in a rare controversy, with some of her fans complaining that she’d put racial solidarity over her bond with them.

“It was harming her numbers — harming her business actually,” said Janice Peck, a University of Colorado who has written on Winfrey’s impact. “She’s pulled away from that” to protect her “brand,” Peck said.

Stewart, though, may not face the same audience blowback, even if his audience isn’t quite as liberal as often assumed.

“He’s got a heavily, young, Democratic progressive audience,” said Steven Ross, a historian of Hollywood and politics at the University of Southern California, who said Stewart would give himself cover with the argument that, “It’s not political, it’s just a statement of disgust.”

And indeed, Stewart’s main challenge will likely be one of performance, not ideology.

“He risks not being funny. If his humor does not work with a large outdoor crowd, or if it fails to register on the small screen, he will look like a self-aggrandizing player inside the political scene rather than a witty satirist located outside it,” said the television analyst Andrew Tyndall. “For Stewart to succeed, he must make a triangle of positions in the political sphere — politicians-activists, journalists-pundits and a third space, equidistant from both, commentators-entertainers.”

“The whole thing turns on the quality of his performance,” said MSNBC’s O’Donnell, who predicted that “the only problem he’s going to have is acoustics.”