A Tribute to David Letterman's Best Stupid Politician Tricks

Rating the performances of presidential hopefuls and one ex-president on the “Late Show With David Letterman,” just as Obama makes his last appearance.
Photographer: Getty Images

Tonight, President Obama will make his eighth and final appearance on “Late Show With David Letterman,” so we know what to expect. The way he is with Dave is the way he is with just about everything: Smart, composed, with better comedic timing than you’d suspect … but still sort always sort of removed from the situation, always talking to a theoretical version of you rather than the actual you. It’s why his best-ever talk show appearance remains his Between Two Ferns chat with Zach Galifianakis:

It used his barely hidden disdain for the public theater of politics to sharp, hilarious effect.

Still, he’s had some fine set-piece moments with Dave. Here is one of his first appearances, when he was running for the nomination in 2008 and popped in via remote to deliver the Top Ten list. I love the way he sells the Mitt Romney joke. 

His most recent appearance was September 2012, right after the conventions, when he gave Letterman a full show. He was relaxed and comfortable, but Letterman didn’t make it easy on him: As Letterman has grown as a broadcaster, he has become a reliable cut-the-bullshit interlocutor, whether he’s talking to President Obama, Jack Hanna, or Paris Hilton. 

Still, Obama—who in fact was the first sitting president ever to go on Letterman’s show—isn’t a signature Letterman guest the way some other presidential-level politicians are. With apologies to Herman Cain, Chris Christie (who ate a donut and made a rather terrific joke), and John Edwards (who, like with everything else, seemed really charming at the time and seems almost sinister now), let’s focus on the big dogs of politics over the last three decades. The presidents, the man who were almost president … and, perhaps most memorably, the women who could be the next one.

George W. Bush

Dubya was perhaps Letterman’s most constantly needled target, if only because Bush’s plain-spoken, sometimes dunderheaded, amiably fratty way of speaking was right in Letterman’s wheelhouse: Letterman’s dumb-guy voice is the voice Bush’s enemies imagined was constantly playing in his head. In the beginning, though, before 9/11, Bush was relaxed and funny and downright genuine, particularly when “explaining” the time he called New York Times reporter Adam Clymer an “asshole.”

Once Bush got closer to Election Day, he was less relaxed and pretty clunky doing his own Top 10 list, though there is a great line about putting together an executive order to make “my brother Jeb wash my car.” 

After he was elected, Bush never showed up again. Probably for the best: Bush was never skilled (pace Steven Colbert at the Correspondents’ dinner) at being in on the joke.

Bill Clinton

Bill is arguably America’s best talker—a friend once said after meeting Bill that “he makes you feel he’s a guest on a talk show you personally host”—and he’s as impressive with Letterman as he is with everyone else. Not that there are not flaws. He has a tendency to get a little pedantic and in the weeds on side topics on a show with a quick clock, but no one in the world is better at telling an anecdote—the most important job of a talk show guest—than Bill Clinton.

Hillary Clinton

Hillary Clinton is, by all accounts, a funny person in real life, but the talk show is just not the right format for her. On Letterman, with its comic Midwestern vibe, she can seem a bit more comfortable. She plays around with Paul Shaffer, she tells an amusing story about catching fish, she laughs at Dave’s jokes convincingly, and even gets in some good pantsuit lines. Clinton may never be a natural couch guest, but awkwardness is part of the point of Letterman—so she can fit right in. 

John McCain

One of the most pivotal media moments of the 2008 campaign was Letterman’s relentless mocking of McCain for canceling on his show in the midst of the economic crisis … and yet still talking to Katie Couric just down the street. It was a bit unfair of Letterman—canceling on his show is not the mortal sin he made it out to be—but it did jibe with the narrative at the time: That McCain was grandstanding and campaigning at a moment of deep import rather than trying to help. Letterman’s dissection of him, with Keith Olbermann as fill-in guest, of all people, still stings.

It’s forgotten that McCain was a longtime friendly face on Letterman’s show. (Actually, McCain might be the best political talk show guest of all time.) He even announced his candidacy in 2007 on Letterman’s show.

Not that anyone will ever remember that. It’ll always just be McCain, obliviously having makeup put on while Letterman destroys him a month away from the election, with the whole world to see. Letterman’s jokes about Sarah Palin, and especially her daughter, are the reason many right-wing sorts think Letterman is a lefty. But he never actually affected politics more than his McCain roast.

Mitt Romney

We just have to include this one because, as usual, Mitt is stiff and formal and so fundamentally decent by nature that you sort of cheer him on when he finally delivers a laugh line right. And they’ve given him some good Top Ten jokes. “I have no proof … but I have a feeling Canada is planning something.”