Oprah: So let's go back to five years ago when it was first announced to us, the public, that you were going to be leaving The Tonight Show. How did that come about?
Jay: I was in my office, and one of the executives came and said: "Listen, Conan's getting offers from the other networks. We don't want to lose him. We want to give him the show, and we're asking you to leave," essentially. And that was pretty shocking.
Oprah: This is in 2004. Had there been a prior discussion that, at some point, you would hand the show over to Conan?
Jay: No. ... I assumed that as long as you're keeping something number one, you remain number one. And, then when you start to slip or [there are] indications that you're slipping, that's when you step down.
Oprah: When they came into your office—"they," the NBC executives—came into your office, your show is number one in nighttime, and tell you that you're going to be moving out in five years, what is your first reaction to that?
Jay: It broke my heart. It really did. I was devastated. This is the job I had always wanted, and it was the only job that ever mattered in show business to me. It's the job every comic aspires to. And it was just like: "What? Why? What is it?" "Well, we're getting pressure here, and Conan's people want to make this announcement and to make sure you do leave, we want to announce it right now, you know, prior to the five years." And I said, "Can't we at least wait?" As I said the other night on my show, couldn't you wait until I'm number two and then say, "Okay, you dropped to number two."