Conan O'Brien doubles down on late-night comedy

Conan O'Brien's show has become more distinctive than ever, doubling down on comedy for comedy's sake.
Conan O'Brien's show has become more distinctive than ever, doubling down on comedy for comedy's sake. PHOTO: FACEBOOK/ CONAN O'BRIEN PRESENTS: TEAM COCO

NEW YORK (NYTIMES) - In September, Tom Cruise stepped into a car with Conan O'Brien and, with his characteristic exuberance, exclaimed that he was ready to sing karaoke or talk comedy. O'Brien waved away those ideas. "My thing, Tom, is take it back to basics," he said, before describing his plan: "Two guys, just driving." What followed was not a spoof of James Corden's signature Carpool Karaoke but something delightfully weirder than that. This 11-minute video began as cringe-comedy performance art, with Cruise bored and baffled, and O'Brien, quietly driving, as a hostile, frighteningly intense version of himself. Then the narrative turned into a kind of thriller as the hero, Cruise, in his best comic role since Tropic Thunder, slowly realised he was trapped with a maniac and needed to take desperate measures. It was the funniest bit on late night I had seen all year.

Among the scrum of late-night hosts, Conan O'Brien - who is set to shoot his TBS show, Conan, at the Apollo Theater beginning Monday as part of the New York Comedy Festival - is not earning the highest ratings or generating the most talk. But his show has become more distinctive than ever, doubling down on comedy for comedy's sake. Now that New York magazine has called Jimmy Kimmel the new Walter Cronkite, and Jimmy Fallon and Stephen Colbert pursue viral moments with games or political diatribes, O'Brien suddenly seems like not only the sole host in the time slot truly desperate to make you laugh, but also the most willing to take artistic risks.

Maybe he really is just going back to basics. It's easy to take O'Brien's gift for refined silliness for granted, since he has been doing the job for nearly a quarter century. His show still looks a bit like what Johnny Carson did for decades: emerge from a curtain to big applause, deliver a topical monologue, then move to a desk, banter with a sidekick, do a comedy bit and talk to guests.

Instead of shying from appearing old-fashioned, O'Brien now uses that image, poking fun at himself, which was part of the joke of the Tom Cruise bit, but also earnestly embracing his status as the eminence grise of late night. When his sidekick, Andy Richter, ad-libbed a line a few weeks ago that referenced Jack Benny, O'Brien laughed, adding, "Could you send everyone a letter telling them who that is?" After a break, he brought up Benny again, recommending him to the audience, surely the only plug that this comedy legend has received on late night in a long while.

In his first years on TBS, 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, with serious-looking people in white lab coats, evoked Albert Brooks' classic send-ups of the conventions of comedy.

Just because the premises of these sketches are tethered to a tradition doesn't mean they aren't peculiar. 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 O'Brien, generally speaking, aims for jokes that depend less on the news cycle than his competitors do.

This even extends to how O'Brien handles politics. While he does an ordinary joke or two about President Donald 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. 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 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 travelled to the West Bank barrier, he bumped into pro-Palestinian activists, who criticised 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 criticised for bias, but wading into this dispute, even clumsily, displayed an admirable willingness to take risks.

Earlier this year, there were rumours 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 politicisation 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.