Conan O’Brien entertains hundreds of thousands of people each year. On a recent clandestine trip to Cuba, however, the TBS latenight host had to please just one – and for several harrowing minutes, thought he had failed.

O’Brien quietly journeyed last month to Cuba in hopes of giving viewers a taste of Cuba’s culture now that President Obama has declared the United States will “normalize” relations with the island country just 90 miles off the coast of Florida.  A group of four (“Conan” executive producer Jeff Ross, head writer Mike Sweeney and O’Brien’s personal assistant were in tow) was to meet up with six staffers – camera crew, audio technicians and writers who had flown in from Toronto. O’Brien and team, who had not informed many executives at TBS owner Turner Broadcasting or its parent, Time Warner, of their trip, did not have visas ready to produce, only documents saying they had been invited to visit Cuba to take part in a cultural exchange.

The official who greeted them at Cuba’s Jose Marti International Airport wasn’t impressed. And the group discovered their smartphones were no longer connected to any kind of service.

“We handed him this form we had been told takes care of everything. He looks at us. ‘No!’ ‘No!’ And then he folded up the paper and he walked away,” O’Brien recounted over lunch with a group of reporters in New York last week.  “And Jeff and I were sitting there. We don’t know if he’s coming back. If he isn’t coming back, we have no phones. We’re in Cuba. We had this idea. We thought it was pretty cool. We might just be completely f—ed.”

Such are the risks one must take to keep latenight TV fresh. O’Brien has been at the helm of a latenight talk show longer than everyone currently on TV except David Letterman, and feels a need to explore new avenues. After being on the air for about 22 years, “The only way you can keep going at a certain point is to change, and to grow up and try different things,” he said, and “maybe try a different muscle.” Viewers will be able to see the results Wednesday night at 11 p.m. on TBS as part of a special that will bear only a small resemblance to O’Brien’s regular program, “Conan.”

His desire comes as two venerable latenight institutions – David Letterman and Jon Stewart – have announced their exits. Stewart recently told viewers that he had grown “restless” after hosting Comedy Central’s “The Daily Show” for more than 16 years, and he is expected to leave his perch sometime between July and the end of 2015. In a moving monologue delivered in 2014 to his studio audience, Letterman told a story about how his efforts to identify a bird with his son had captured more of his attention than the CBS program he has led for years. He will leave “The Late Show” in late May. The secret of working in latenight is that the job injects the host regularly into popular culture, but the staff behind the programs must hurl themselves through an onerous process night after night after night to keep things going.

O’Brien’s Cuba sojourn also takes place as the economics of latenight are shifting. More of the signature moments from nearly every program in the genre, whether it is O’Brien’s “Conan” or Jimmy Kimmel’s “Jimmy Kimmel Live,” are seen not as they air on the shows themselves but on streaming video passed along the morning after. Speaking to investors last week, NBCUniversal CEO Steve Burke noted that 70% of the views for NBC’s “Tonight Show Starring Jimmy Fallon” came from digital media, most of which can’t be monetized at present.

Meanwhile, viewers seem to crave more authentic material, said O’Brien. “They really like seeing you out and unscripted and sort of having these adventures and it is not that processed. A lot of them have grown up with reality TV. This is actually more real than reality TV — because we don’t really script them,” he added.

Pursuing a new path could lend O’Brien’s “Conan” more distinction, particularly as the number of wee-hours programs has expanded over time. “I still love the form, but in a world where there are more and more and more and more shows, there actually is an impetus to — all right, I want to keep changing,” he said. “I want to do something radically different than I would have done 10 years ago.”

In a different era, an unsanctioned trip abroad to a dangerous locale by one of the nation’s longest-serving latenight hosts would be cause for something grand. Announcements would be made. A large crew would be procured. Video from the trip might be aired and posted in hopes of sparking anticipation. Instead, O’Brien and his team made their excursion in guerrilla fashion, hoping to keep the project quiet out of fear of alarming authorities and having the whole thing shut down.

In Cuba the team tried to stay out of mainstream restaurants, which are largely government-run. They were forced to stop shooting in a grocery store, because workers there wanted to get permission from officials. To lend the program some resemblance to his normal show, O’Brien borrowed a table at a café, put an old microphone on top of it, and asked a group of female musicians to serve as his house band.

The idea was not to do the typical man-on-the-street piece that makes fun of people who agreed to talk, O’Brien said. “I felt really strongly about it. I do not want to do what is going to be a snarky, American comedy take. I don’t want this to be political.” Instead, he said, he aimed to portray himself as “a fish out of water” where “the joke is usually on me.” Viewers will see O’Brien try to make Cuban cigars and sing Cuban music.

If viewers liken his Cuban adventure to something Anthony Bourdain might do on CNN, O’Brien seems comfortable with that.  “I could see doing remotes in high definition in different parts of the world with more of a comedic bent” should he face a career change in the years ahead, O’Brien said. “I love travel and I love exploring things, and I love trying to see if I can make someone laugh in a different culture.” His most satisfying moments during the trip, he said, came in “just getting people to laugh who might not speak very much English, don’t know much about our culture, but they understand this guy not being able to make a cigar, not being able to play this music.”

The comic also grappled with Cuba’s shoddy record on human rights as he made his visit. O’Brien carried with him a memoir by Reinaldo Arenas, a gay writer who was imprisoned in Cuba, partly to see if it would cause any problems. It did not. “I don’t think that it’s a great place to be an artist. I don’t think think it’s a great place to be a homosexual,” said O’Brien. “The question is what is the best way forward and what is the best way to get it to change.” Promoting better access to the Internet and more exchanges of information with other countries, he suggested, would be great steps.

Was O’Brien suggesting he sees a day when he too might step down? Not necessarily. He likened the role of latenight host to that of a farmer who keeps people fed or an eye surgeon who helps people see. Should these folks retire just because they’ve learned many of the nuances of their craft?

“The fight now is to keep it interesting,” O’Brien said. “Let’s try and surprise ourselves and maybe surprise people who wouldn’t expect it. And in a weird way, maybe this is not a bad form of diplomacy.”