Photo: Dimitrios Kambouris (Getty Images)

In the current stable of late-night hosts, no one has been in the game longer than Conan O’Brien. That feels weird to say because, once upon a time, he was the sweaty, wide-eyed rookie in a field of veteran showmen. But after 25 years behind the desk at Late Night, The Tonight Show, and Conan on TBS—which will soon transition to a half-hour format—O’Brien has experience that few others have. He’s presided over a tumultuous, transitional period in late-night, where a conversational, slow-paced program has been pushed aside in favor of shareable, viral segments. This week, Conan sat down with Vulture to talk about his firsthand experience with the ever-evolving format.

“I used to love doing a whole hour; that was my assignment…but at a certain point you start thinking, ‘Wait a minute. Why am I still doing it the way I’ve been doing?’” Conan says in reference to his decision to halve the length of his show. Back in the day, he explains, late-night talk shows were put on the air to take advantage of a time slot that nobody else was using. They used the whole hour, because there wasn’t anything else there. As TV evolved and the landscape got more populated, the format remained stagnant. That left Conan feeling like he was vamping to fill an hour of television when he’d be more excited to have a single guest or just do a 30-minute travel show. “At this stage in my career doing a half an hour could shock me into coming up with new stuff.”

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But for some viewers, even a half hour is too much to invest in a single show, and Conan is well aware that, while his TBS show isn’t topping the ratings each week, his shorter segments that get shared online rack up millions of views. While this might seem frustrating from a business stand point, Conan seems to have a made his peace with it, and actually gets a little creative charge from figuring it all out:

The thing is, I’ve got 16-year-old fans that stop me and go on about Clueless Gamer. The fact that my show will be half as long is going to mean nothing to those teenagers — even though I want to explain to them, “I’m 78 years old and I’ve been doing this for a long time! I fought in the Korean War, you punk!” But the important thing is to make the stuff. Then we figure out what goes on the show, what goes directly online, what is put out as a caffeinated drink, what becomes a saline solution that goes in your eye.

Later in the interview, Vulture asks the question that gets asked of every entertainer whose been in the business for more than ten years: Do you ever think about hanging it up? “Yeah, I do, but maybe not in the expected ways,” Conan says. Remarking on the difference between Johnny Carson’s retirement from television and David Letterman’s “retirement” from one talk show format to another, Conan thinks there’s no reason why the end of one particular show has to mean the end of his career in television all together.

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You can read the whole interview here, which includes some of Conan’s thoughts on the whole Tonight Show debacle and how he deals with difficult guests.

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