In this case as well, the content started with the president. As Seth Meyers, the host of NBC’s “Late Night,” told Vox recently, “The White House has the best writers’ room in comedy.”
Where football is any given Sunday, late-night comedy is every single weeknight. And with its harder charge into anti-Trump political humor, it has sailed into what the former New York Times writer Bill Carter called “absolutely uncharted” territory.
I checked in with Mr. Carter not only because we are old colleagues but also because he is the nation’s foremost student of late-night entertainment. He literally wrote the book on it — that is, “The Late Shift,” the classic yarn about the war between David Letterman and Jay Leno to get Johnny Carson’s job on the “Tonight” show. (He followed it up with “The War For Late Night,” about the Conan O’Brien debacle at NBC.)
“There’s no example of any kind of sustained attack like this on a politician,” Mr. Carter told me last week. “There’s a horde of writers writing jokes about Donald Trump every single night.” (And, he said, he wasn’t even counting the weekly shows like “Saturday Night Live,” “Last Week Tonight with John Oliver” and “Full Frontal with Samantha Bee.”)
This has brought about an abundance of incisive political satire. But it has also come with new complications that threaten to kill the fun, through blowback on the pro-Trump right and the rigid expectations of an anti-Trump audience that wants Resistance TV every night.
Mr. Colbert bumped up against the latter when he hosted the Emmys last week and decided to do a bit with the former Trump press secretary Sean Spicer. His writing team from “The Late Show” knew it might not be well-received in some quarters and debated the idea ahead of time, people familiar with the deliberations told me (they spoke on condition of anonymity so as not to be seen as violating the sanctity of the writing room).
By normal comedic standards, the idea seemed pretty basic: Put Mr. Spicer behind a mock White House lectern and have him make a fake boast about the size of the Emmy audience — evoking the false claim he made about Mr. Trump’s inaugural crowd. The sketch fast became heckler…