In one of their final head-to-head guest-booking battles earlier this year, ratings king Jay Leno beat David Letterman yet again, becoming the first host of a late-night entertainment talk show to interview a sitting president.
But Letterman's sitdown with President Obama, broadcast Monday night, may go down as more memorable, controversial – and funnier.
"We told him Megan Fox would be here," Letterman said, offering one of the Top 10 reasons the President agreed to appear on “Late Show.” Reason No. 2: "Said ‘yes,’ without thinking… like Bush did with Iraq."
Obama's March appearance on "The Tonight Show" largely played out as an amiable chat, though the President raised some ire by referring to the Special Olympics while joking about his poor bowling skills.
Obama's appearance Monday night – depending on your point of view – was perhaps the boldest, riskiest or least appropriate stop on his healthcare media barnstorming tour.
The stakes also were high, in a very different respect, for Letterman. While he lambasted President Clinton with little mercy during the Monica Lewinsky scandal, Letterman’s humor turned more acerbically political during the Bush years. From the Bush-bashing "Great Moments in Presidential Speeches" bit to his post-administration shots at Dick Cheney to dustups and tentative make-ups with Sarah Palin and John McCain, Letterman hasn’t exactly been a pal to the GOP.
But Letterman didn’t roll over like a Stupid Pet Tricks lapdog for Obama. He asked reasonable, if not always hard-hitting questions, and put his sharp wit to use even as he gave the President ample opportunity to talk about the economy, Afghanistan -- and healthcare.
Asked by Letterman about the possible role of racism in criticism of his presidency, Obama quipped, "First of all, I think it's important to realize that I was actually black before the election."
“How long have you been a black man?" Letterman shot back.
Accustomed to playing the cranky clown, Letterman walked a tightrope, trying to stay true to his sardonic style while maintaining his respect for the office of the president. Obama’s challenge was to maintain respect for the timeslot – firing off some jokes (on how he wound up on Letterman: “You ask your advisers, ‘Who’s responsible for this?’”), while sticking to his healthcare talking points.
"Your job is more difficult than my job," Letterman told Obama.
Both men's jobs are changing, at least in terms of their media roles.
Politicians are proliferating on late-night entertainment programs, not only “Saturday Night Live,” “The Daily Show” and “The Colbert Report,” but on less traditionally politically pointed broadcasts. The pols apparently see the talk shows as an opportunity to make their cases direct to the people – or at least the people who watch late-night talk shows.
Obama, to the distress of some critics, has turned up repeatedly on entertainment shows since being elected. In addition to sitting for interviews with Leno and Letterman, the President welcomed Conan O’Brien to “The Tonight Show” in a video gag, appeared on “The Colbert Report” via satellite and even taped a promo for George Lopez’ new TBS program.
But taking a legislative battle to an entertainment program is a new strategy for Obama – and uncharted territory for Letterman. The host’s best known moments over the years largely have been generated by the confrontational and the unexpected – everything from Madonna’s potty mouth to Joaquin Phoenix’s bearded zombie act – not from presidents pitching policy.
Still, the Obama appearance could wind up on Letterman’s Top 10 list of most memorable shows.
Hester is founding director of the award-winning, multi-media NYCity News Service at the City University of New York Graduate School of Journalism. He is the former City Editor of the New York Daily News, where he started as a reporter in 1992. Follow him on Twitter.