Obama on Letterman and What I’ll Miss in Late Night Television

President Obama on Letterman

A little over two weeks ago, Conan staff writer Andrés du Bouchet got himself in a bit of trouble by whining about the state of late night comedy on Twitter. Since deleted, here’s what the tweets amounted to:

Comedy in 2015 needs a severe motherfucking shakeup. No celebrities, no parodies, no pranks, no mash-ups or hashtag wars. I’m fat. … and shove your lip-synching up your ass.

Prom King Comedy. That’s what I call all this shit. You’ve let the popular kids appropriate the very art form that helped you deal. Fuck. None of the funniest stuff ever involved celebrity cameos.

The tweets were in poor taste, but they struck a chord with me. The target of the criticism was surely Jimmy Fallon, but Jimmy Kimmel seems just as guilty. I don’t think it’s fair to necessarily call either host “the popular kids,” but “Prom King Comedy” rings true. Which is to say not really comedy at all, just dress up skits.

I can’t watch Fallon’s Tonight Show because I simply have no interest in the snackable, made-for-YouTube look-at-what-I-can-do bits. His show may be fun, but I don’t find it funny and, generally speaking, I wouldn’t really call it a comedy show. The sketches feel like a crutch, propping up the host to keep him from interviewing guests.

The Tonight Show today is wildly popular, and I don’t begrudge anyone for enjoying it before bed (or, more likely and by design, at work the next day). But to me it’s not a late night talk show. It’s a different thing than what I grew up with; a different thing than what I want in the evenings. And that’s fine. Perhaps the comedy talk show is done for. Maybe we’ve moved on from a format that worked for decades to something else.

Which brings me to David Letterman interviewing Barack Obama last night. Letterman, the elder statesman of late night television, is closing in on his final show. He’s stacking the deck with high profile guests and longtime friends on each outing. Having the President come on seems appropriate for the occasion.

It has been common for politicians to stop in on comedy shows for decades now to show off their softer side. These shows appeal to a younger, often-times not-politically minded crowd. The hosts are often friendly and welcoming in a way that makes it easy to get your agenda out in front of the public. Plus you get to be funny and appear soft and relatable. Everyone wins.

But it’s always been different with Letterman. He is a brilliant comedian, but an even better broadcaster. He has an extra muscle that allows him to know what makes great television, and he’s never been afraid to use those skills in front of the camera. On Letterman’s stage, no guest, no matter how powerful can outsmart him.

Perhaps the most famous example of Letterman’s broadcasting (and, arguably, political) prowess occurred on September 24, 2008, when John McCain, then deep in his failed campaign for president, canceled a Late Show appearance so he could go back to Washington to work on the faltering economy. Letterman’s response was to tear into the presidential hopeful. His master stroke was broadcasting the CBS News live feed of McCain, still in New York at the time of the taping, getting his makeup put on in preparation for an interview with Katie Couric. As Bill Carter puts it in his excellent The War for Late Night:

The event became part of the news cycle in the race. McCain had stiffed Letterman, and Dave made him pay. He got more licks in on McCain for several nights after, and McCain ultimately had to make a date in his otherwise packed calendar to return to New York (a state he was hardly going to win) on October 16 to formally seek Dave’s pardon.

It’s hard to think of any other late night host, past or present, who could have pulled off such a stunt. McCain went head-to-head with Letterman and lost. Today we think of our television personalities, even many of our news anchors, as lightweights, fluffy sounding-boards against which any candidate, analyst or celebrity can speak rehearsed talking points. That’s never been Letterman.

His interview with Obama last night certainly wasn’t hard hitting. The President rolled out a few obviously scripted zingers and Letterman tried to lighten the mood. But for the most part the conversation was deeply serious. They discussed poverty, race relations, policing, riots and how to help disabled veterans when they come home.

Where Letterman is a deft broadcaster, Obama is a staunch politician. And so almost none of what comes out of his mouth is off the cuff. Yet there is something so refreshing about seeing him asked about specific, major issues of the day.

Letterman is so good at getting to the heart of big questions, the conversation seemed like it could go in any direction. I wondered while watching, for example, if Letterman might ask the president to explain his sweeping drone strike strategy. Only a week and a half ago a contrite Obama admitted to the accidental killing of American and Italian hostages. Though Letterman didn’t go there, he could have, and he could have done it in a way that no other broadcaster today could.

And that’s what I’m going to miss when he’s off the air. Letterman holds court in the Ed Sullivan theater. He can mete out truth from his guests while keeping them comfortable enough to have a few laughs. That mix of off-the-wall comedy (earlier in the show Will Ferrell reprised his SNL Harry Caray impersonation from the audience) and plainspoken talk show is what makes late night television such a fertile and interesting space.

All of that is a long-winded explanation not only of why I’ll miss Letterman, but, ultimately, why I don’t like Fallon’s Tonight Show and its ilk. As Obama explained to his questioner the state of race relations in our country today, I turned to my girlfriend and asked if she could ever imagine Fallon doing an interview like this. She laughed.

“No way. They’d be playing the dunce game by now,” referring to a trivia sketch that ends when either the guest or Fallon, each in a pointy dunce cap, pops a water balloon positioned over his or her head. Fun, but funny?

There is room for so many types of shows and hosts, but I hope that we don’t lose the format that has been a cornerstone of American broadcasting for so long. As the powerful get savvier, so too must our interviewers find ways to break down the barriers to honest conversation. Letterman is the best at it. Hopefully soon someone else will be.1

  1. I actually think Stephen Colbert, Letterman’s successor, is great at precisely this type of interview. His learning curve on CBS will be whether or not he can be likable up against the likes of Fallon, whose populism, I don’t know if I’ve made clear, has clouded his ability to be much more than friendly face. ↩︎