During Letterman’s opening monologue last night, he quipped: “It was so cold here in the New York area today, Chris Christie was wearing two giant sweaters.” Then, irked by the weakness of his joke, he asked writers Joe Grossman and R.J. Fried to come onstage and punch it up, and—after running through some alternatives (“It’s so cold, Taylor Swift wrote a song about breaking up with her shorts”)—they landed on “It’s so cold, I chipped a tooth on my soup,” before being kicked offstage. A little later, in a bit where Dave made him guess the atomic numbers of various elements, music director Paul Shaffer had a voiceover monologue wondering what poor life choices had led him to this sorry moment. Both of these are classic Late Show bits: comfortably within the “so cold I chipped a tooth on my soup” realm of classic, broad, network nightly-show humor, while gently ribbing the very flaccidity of that style.
But then John Oliver took the stage. Oliver, who was Letterman’s guest in advance of the Feb. 8 Season 2 premiere of Last Week Tonight, began regaling the host with anecdotes about tasering himself while entertaining troops in Afghanistan and watching a man try to steal a whole side of beef during a summer job in the freezer section of a slaughterhouse. And seeing Oliver and Letterman’s distinct styles bump up against each other offered a revealing window into the old vs. new guard of late night. The currency John Oliver trades in is substance—the packaged delivery of information and argument, while Letterman dwells lovingly in daily ephemera. “I heard you had a bad job once” is exactly the kind of question the Late Show With David Letterman asks. “Here’s 16 minutes of well-sourced argument outlining the corrupt use of civil forfeiture in America's police departments” is an answer Last Week Tonight With John Oliver gives.
Letterman remains the kind of show where half the jokes are literally about how tepid the jokes are, while, when John Oliver dumps a 400-page stack of Miss America research onto his desk, his only joke is just how ridiculously well-substantiated his joke is. It’s basically the same gag—we tried hard, but we ran out of time—but one played for “You love it because it’s dumb” and one played for “You love it because you’re learning something.” So when Letterman lobbed the softball “Are you going to watch the Superbowl” question at him, Oliver—who has taken jabs at the NFL on his own show—took the opportunity to declare: “It’s patriotic, it’s religious, it’s happy, it’s sad, it’s incredibly dangerous on a personal level, and Pepsi sponsored the whole thing...when you beam that around the world everyone else is thinking ‘if they’re capable of this, what else can they do?” The Late Show and Last Week Tonight, needless to say, are shows with very different goals. And it remains to be seen how much Stephen Colbert, when he takes over the Late Show gig, will really be able to push the late-night envelope in light of the rigid expectations of the form. But watching Letterman and Oliver side-by-side still felt like kind of like seeing the clash of Late Night Past and Late Night Future play out before our eyes.