In a career studded with historic firsts, President Obama is preparing for yet another: hitting the late-night comedy circuit to pitch his economic recovery plan.
It's hardly a laughing matter, with the country in its worst economic shape in decades. And it certainly doesn't approach the import of Obama's election as the nation's first black president.
However, by taking a seat Thursday night on "The Tonight Show with Jay Leno," Obama will become the first sitting president to appear in such an unlikely venue, erasing -- perhaps once and for all -- any vestige of the line that separates news from entertainment.
It will also extend Obama's habit of speaking past the Washington press corps and ditching the capital for events that distance him from the Beltway status quo; for those keeping accounts, Obama may be sending a signal by going on the "Tonight Show" and then skipping Saturday night's Gridiron Club dinner.
The evening of music and comedy hosted by an exclusive Washington journalists' organization is a white-tie highlight of the capital's social season. But Obama plans to spend the evening with his family, becoming the first president since Grover Cleveland not to show up for the first Gridiron dinner of his presidency.
"He's kind of setting a tone that he's not going to be restrained by the rules," said Michael Dimock, associate director of Washington's nonpartisan Pew Research Center
There is every chance that Obama will fall flat on the "Tonight Show," given the dismal topic. Country singer Garth Brooks is the musical guest, and even the most heartbroken girl-done-me-wrong performance may seem carefree by comparison.
But for Obama the unconventional appearance is a risk worth taking -- and not just because Leno, as the top-ranked host in his TV time slot, draws 5 million nightly viewers.
The president, who remains personally popular despite growing questions about his policies, is banking on the chance to broaden his audience beyond cable news junkies and political elites, appealing to those who don't already know the intricacies of his budget blueprint and healthcare overhaul plan.
"That's the group he needs to convince that he's doing a good job and his budget makes sense," said Darrell M. West, a Brookings Institution expert on the intersection of politics and celebrity.
Obama will undoubtedly enjoy a more congenial conversation than he would by, say, holding a White House news conference. (On Monday, the president blasted American International Group Inc., the insurance giant, for paying millions in bonuses, then let White House Press Secretary Robert Gibbs face a grilling on why the federal government bailed out AIG knowing those bonuses were in the works.)
Obama has visited Leno before, making his first "Tonight Show" appearance in December 2006, when he was plotting his White House bid. Other successful presidential candidates preceded him on the show, including Richard Nixon and Bill Clinton.
In 1993, Al Gore made history by going on "The Late Show with David Letterman" and shattering an ashtray with a hammer as part of the sales pitch for his reinventing government initiative. But Gore was vice president at the time.
Times staff writer Maria Elena Fernandez contributed to this report.