When a former writer for Saturday Night Live and The Simpsons, an individual with practically no professional background in performing, was given the task of succeeding David Letterman, the consensus opinion was that this new fellow with the distinctive name wasn’t likely to last. Then the revamped program, now dubbed Late Night with Conan O’Brien, made its debut, and outside observers were dead certain that the show wouldn’t last. Initial reviews were savage, and Conan O’Brien and his crew spent the first several months — maybe the first couple years — sure that cancellation was imminent. The sense of doom was a sort of freedom. Already inclined to absurdity, O’Brien presided over a show that aired comedy with no particular attempt to milquetoast taste.

Twenty-eight years later, one year shy of Johnny Carson’s tenure as host of The Tonight Show, O’Brien is officially stepping away from the task of presiding over a night offering of late-night comedy. He didn’t have an uninterrupted run as a host. There were a few gaps in there. Most notably, and notoriously, he was cast into purgatory after a messy, unfairly truncated turn as host of The Tonight Show. He rebounded by going to TBS, a cable network that compensated for what it lacked in reach by offering greater creative latitude. By all accounts, TBS didn’t meddle with O’Brien and his staff, many of whom had been with him since Late Night. They made the comedy they wanted to make, they way they wanted to make it.

Despite the arrows initially shot his way, O’Brien was worth watching from day one. (Well, maybe week four or five.) He took Letterman’s celebration of the odd and mundane and sheared away some of the the protective irony his predecessor relied upon. The comedy was equally ingenious, but it was kinder, with an undercurrent of joyfulness. Like Letterman, O’Brien did some of his best work on remotes, sparking off of people who hadn’t been trained by showbiz convention to couch their reactions. From his time on TBS, few segments capture that spirit better than O’Brien’s visit to a Chicago elementary school to workshop blues songs with the kids. It’s filled with perfectly timed gags, such as the reveal of Tommy’s rhythmic accompaniment, an expert callback to Nathaniel’s plight with hurled balls, and the interjection of a special title card for Olivia.

It’s been a long time since I watched O’Brien’s show with the devotion he earned. I was always glad he was out there, though, still working and following his goofy muse. And he was pretty dang good and coming up with impromptu blues songs based on the suggestions of citizens still sporting baby teeth.