I’ll never forget the look on Conan O’Brien’s face as we sat in his ninth-floor office at 30 Rockefeller Plaza one night in 2003 and he described the humiliation he had experienced a decade earlier when he succeeded David Letterman as host of a late-night show on NBC.
Up to that point, O’Brien had spent most of his career as a writer (”The Simpsons,’' “Saturday Night Live’'), not as a performer. As the Brookline native and Harvard grad tried to find his footing in front of the cameras in 1993, the verdict from TV critics was utterly blistering.
NBC stopped just short of canceling “Late Night with Conan O’Brien,” but the network clearly signaled it was poised to lower the boom by forcing O’Brien to struggle ahead on 13-week contracts. That was an insult he did not forget, even though by the time we spoke he was riding high, having deployed his singular comedic and conceptual gifts to establish his show as must-see TV.
“You know the Clint Eastwood movies where they beat the crap out of Clint Eastwood and then hang him but then ride off and forget to kill him?” O’Brien asked me. “When he comes back and walks through the flames and everyone’s like ‘Omigod, it’s him!’? It’s kind of like ‘Hey guys, you forgot to kill me, and now I’m back’.”
O’Brien paused, then added with a faint smile on his face: “So the bar gets really quiet when I walk in.”
Clever, yes, but there was unmistakable anger beneath the trademark wit. And there was another, much bigger blow at the hands of NBC in store for O’Brien down the road, when he landed his dream job as host of “The Tonight Show,” only to leave it in less than a year after a highly publicized fiasco involving Jay Leno.
But O’Brien proved both resilient and adaptable. He launched “Conan” on TBS in 2010 (and, later, a podcast, “Conan O’Brien Needs a Friend”) and he eventually achieved a status that few would have envisioned for him back in 1993, becoming the longest-tenured current host of a late-night TV show.
Indeed, O’Brien’s 28-year-run, first on NBC and then on TBS, rivals the epic late-night tenures of Letterman (33 years) and Johnny Carson (30 years).
To be sure, his viewership numbers on TBS are not anywhere near what they would have been had he stayed on NBC, and “Conan’' was downsized to a half hour a couple of years ago. But it hasn’t constrained the freewheeling comic imagination that makes Conan Conan.
Last November, it was announced that “Conan” would wrap up this summer, and this week came word that the end date will be June 24. That will not be the end of O’Brien’s television career, however. He has inked a deal with WarnerMedia, the parent company of TBS and HBO, to produce and host a weekly variety show for the streaming platform HBO Max, and he will continue to be a presence on TBS with “Conan Without Borders” travel specials.
As he prepares to step down from late night next month, O’Brien’s longevity — and unflagging creativity — entitles him to feel a measure of vindication. At the end of my interview with him in 2003, he recalled a day when he was in his 20s and sitting at a diner in Los Angeles, broke, unemployed, and thoroughly bummed out: “And I remember just, almost like a prayer, saying to myself: ‘I don’t care what happens to me as long as it’s interesting. Please, God, whatever happens to me, let it be interesting’.”
At a minimum, it has certainly been that.