4,368 Episodes Later, Conan O’Brien’s Late-Night Run Ends

“Conan” has been on cable channel TBS since 2010, but this send-off is effectively for Mr. O’Brien’s entire run as a late-night host, which started in 1993 and included two previous shows on NBC. Next he’ll head off to streaming with a new weekly variety show for HBO Max (which he recently mocked in a bit comparing HBO Max’s business model to a pyramid scheme). He has also been pulled away from traditional TV by other projects from his Team Coco production company, including his long-form interview podcast “Conan O’Brien Needs a Friend.”

In 2019, Mr. O’Brien dispensed with his host’s desk and trimmed “Conan” to fit a 30-minute time slot. Despite the many changes he has weathered on the air, the host’s style has remained consistent—a balance of relentless self-deprecation and faux demagoguery. He turned his shows into a vehicle for surreal silliness, and influenced a rising generation of comedians who watched him. As former “Saturday Night Live” star Bill Hader said when he appeared on Mr. O’Brien’s show this week, “It was the first thing in comedy that was mine. It was the first thing that, like, my parents didn’t understand.”

Among countless sketches on the 4,368 episodes that Mr. O’Brien and his collaborators produced, here are five examples that mark the evolution of his late-night run:

Absurdism unleashed

Though the former “Saturday Night Live” writer was an unknown when he took over

David Letterman’s

post-midnight time slot on NBC in 1993, “Late Night With Conan O’Brien” immediately stood out as something different. “Letterman took an ironic position to the talk show,” Mr. Ross says. “We did the absurd version of the talk show.” Fake guests included

Bill Clinton

(talking out of someone else’s mouth). Head writer Robert Smigel introduced his Triumph the Insult Comic Dog. And Mr. O’Brien and sidekick Andy Richter made goofy predictions for the year 2000—a recurring routine that lasted long past the turn of the millennium.

These would become classic bits. At first, however, the show was panned and faced long odds of survival at NBC. “When we knew there was trouble we just put our heads down and ignored everything. Luckily we were in New York, and they [the network executives] were all in L.A.,” Mr. Ross says.

Out in the field

Even after his show had started to charm critics, Mr. O’Brien used his status as an underdog on TV’s graveyard shift for his popular remote segments. in his underdog status on TV’s graveyard shift. In 1997, he personally went searching for viewers in Houston where, due to local scheduling quirks, “Late Night” didn’t hit the air until 2:40 a.m. The host attempted to win over people he found in the wee hours in a bail bonds office, emergency room and bus terminal, where he explained to one skeptic: “For the first year and a half, crap. Now, the show is good.”

Exiting “The Tonight Show”

After 16 years of “Late Night,” Mr. O’Brien spent a tumultuous eight months leading “The Tonight Show,” until the host he had succeeded, Jay Leno, took that job back. It was a painful chapter for Mr. O’Brien behind the scenes, but on camera it resulted in some gleeful bridge-burning.

“Until NBC yanks us off the air, we can pretty much do whatever we want and—this is the best part—they have to pay for it,” Mr O’Brien said to viewers in 2010. He described the running gag, featuring a Bugatti outfitted as a mouse with a Rolling Stones theme song, as “comedy bits that aren’t so much funny as they are crazy expensive.”

Utilizing (and mocking) his staff

For on-camera cameos and recurring characters, Mr. O’Brien always relied on his deep bench of writers, many of whom were experienced stand-up comedians and improv performers. More surprising, however, was the comedy mileage he got out of regular staff members. One of the most effective of these in-house straight men was associate producer Jordan Schlansky, whom Mr. O’Brien roasted for his posh tastes and love of Italy.

Going abroad

Whether mocking his own ancestry in Ireland or his resemblance to the (female) then-president of Finland, Mr. O’Brien has long specialized in being a fish out of water in foreign countries. Over time, the host added nuance and educational elements to that schtick in his series “Conan Without Borders.” It took him to Cuba, after the Obama administration relaxed travel restrictions there, as well as to countries such as Ghana, Haiti and Armenia, where he starred on a soap opera and hunted for a husband for his longtime assistant Sona Movsesian.

Write to John Jurgensen at john.jurgensen@wsj.com