‘Why Is This Guy Here? Who Will Be the Real Host?’: David Letterman Shares His Reaction to Conan O’Brien Taking Over ‘Late Night’

When Conan O’Brien first filled David Letterman’s seat on Late Night in 1993, questions similar to “What kind of name is that?” and “How the hell does NBC expect this nobody to follow up the greatest late-night host in history?” echoed across Letterman’s apartment.

The acrimonious ending to Letterman’s time at NBC is the stuff of late-night legend. As Johnny Carson’s closer and protégé, many thought Letterman would be first in line to replace his mentor when Carson retired from The Tonight Show — including both Letterman and Carson. When NBC decided to promote regular Tonight Show substitute host Jay Leno to the permanent position instead, an incensed Letterman jumped ship for CBS to start The Late Show, leaving hurt feelings and hot gossip in his wake. NBC then made the (at the time) puzzling decision to replace Letterman in the role he originated on Late Night with an accomplished but un-stage-tested TV writer who was part of the brain trust in charge of finding the successor. 

Yesterday afternoon, Vanity Fair published its oral history of Conan O’Brien’s tumultuous first year on Late Night, including interviews with Lorne Michaels, Robert Smigel and, of course, Letterman, who admitted that, “My reaction to Conan behind that desk was similar to everyone’s reaction, which was, ‘Now who is this? Why is this guy here? Who will be the real host?’” I imagine Letterman had similar thoughts when he saw Leno and his representatives slip into a conference room with the Tonight Show producers.

“I remember in that overlap transitional period, there was so much attention to the change,” Letterman said of the months following Leno’s promotion to permanent Tonight Show host. “‘Is he going to stay? Is he going to leave?’ In the beginning, it was kind of exciting. And then I soon sickened of the attention because I was unaccustomed to it. It really began to be superficial. And I felt my ego had been set on fire and I can’t possibly stand it anymore.”

After Letterman left for The Late Show and O’Brien replaced him in his NBC role, O’Brien’s first season at Late Night was legendarily rocky as the show struggled to find both its voice and its audience. Meanwhile, Letterman’s new project was a critical and commercial hit as CBS celebrated the beginning of a new late-night empire. In a moment of desperation, O’Brien invited Letterman to return to his old haunt at NBC Studio 6A as a guest — and, to O’Brien’s surprise, his predecessor accepted.

Letterman recalled of the historic guest spot, “It was kind of like, ‘Dave, it’d be great when you’re done with varsity practice if you could swing by and talk to the freshmen.’ It was kind of like that.” Letterman then admitted, “I’m nothing if not self-centered. So I felt like, ‘This would be great for me.’”

It was great for O’Brien, too — the appearance won O’Brien a brief respite from his harshest critics who applauded his humility for bringing on the man whose shoes he was struggling to fill. And, in the process, he won Letterman’s respect. “I remember I was quite taken by the quantity and the quality and the kind of comedy they were doing, which was not similar to anything I had done,” Letterman explained, “I was legitimately impressed by that.”

If quantity impresses Letterman, then he should take a look at the podcast empire Conan commands at Team Coco — maybe he'd follow in Conan's footsteps, for a change.