In his first years on TBS, Mr. O’Brien still seemed haunted by losing “The Tonight Show,” but his series now has the pleasing eccentricity of someone who doesn’t care about ratings or expectations.
In the past two weeks, he has brought on weirdo characters like Butterscotch, part of a long tradition of creepy clowns, and a guy doing a Dracula impression who can’t stop making bad puns (“I don’t want to sound like your mummy but …”), a bit that spun out unexpectedly into a story of addiction that led this bad joker to attend the Lestat Institute for Word Therapy. The fake institute, complete with serious-looking people in white lab coats, evoked Albert Brooks’s classic sendups of the conventions of comedy.
Just because the premises of these sketches are tethered to a tradition doesn’t mean they aren’t peculiar. Mr. O’Brien’s brand of silliness has always been delightfully, often gruesomely askew. Recently, he began a sketch by asking strangers what they thought about the news that Sears would no longer be carrying Whirlpool appliances. But this man-on-the-street premise was only the setup, because after a few people expressed normal curiosity or indifference, one man appeared stunned, immediately called his family, went home and buried himself alive while they watched. The video ended in another interview with a person showing mild interest in the news, but in the background, the family looked down on the grave and set it aflame.
While some jokes are connected to the calendar, like the clown for Halloween, many of them are evergreen. A punch line about the daily goings-on in Washington can get easy laughs from like-minded viewers. But they won’t age well, and Mr. O’Brien, generally speaking, aims for jokes that depend less on the news cycle than his competitors do.
This even extends to how Mr. O’Brien handles politics. While he does an ordinary joke or two about President Trump every night, he also produced one of the most truly daring episodes of political comedy this year, with a September show shot entirely in Israel and the Palestinian territories, one of his many episode-long forays into other cities. Mr. O’Brien floated in the Dead Sea, engaged in some terrible haggling with street vendors and delivered a minute-long history of the area that covered thousands of years.
Much of the special was simply Mr. O’Brien unscripted, making a connection with game strangers and turning that into an amusing scene. But he didn’t only stay light. When he traveled to the West Bank barrier, he bumped into pro-Palestinian activists, who criticized Zionism, describing a Palestinian girl killed by an Israeli settler. He spent most of this awkward but compelling exchange listening, without defensiveness, and then posted the entire 24-minute segment online. Inevitably, his show was criticized for bias, but wading into this dispute, even clumsily, displayed an admirable willingness to take risks.
Earlier this year, there were rumors that “Conan” was shifting to a weekly format, and Lord knows, after being a daily talk-show host since 1993, he has earned the right to a slower schedule. But here’s hoping he sticks around, because more than anyone else on air, he is a reminder that talk-show hosting is an art form deserving respect. The increasing politicization of late-night comedy has been great for ratings, and has helped certain hosts find their voices, but it’s worth examining if it comes at a cost. Comedy doesn’t need to serve a political end to be important.