"I'm proud of you," Stern said. "I read in the paper that Conan is going to replace Jay Leno, thank god. Do you think that's really going to happen?"
"I think it's about a 40 percent chance that's going to happen," O'Brien jokingly replied.
"I don't see this guy leaving and letting you walk in," Stern pressed on. "I'm concerned about you."
"You're concerned, what about me?" Conan said.
It's a conversation cliffhanger that viewers just may be able to hear the end of this week.
Last week, word broke that The Tonight Show bookers were trying to get the notorious Leno-basher and ratings goldmine on as a guest during Conan's final week, and while time is running out, it's possible they may get their wish.
Sure, Stern told his Sirius listeners that his laziness made it unlikely that he would be hopping on a plane to L.A. before tomorrow night, and The Tonight Show has already released its rundown of final week guests (officially, Tom Hanks and Will Ferrell have the swan-song honors).
But the blogosphere is ablaze with rumors that it will be none other than Stern himself who may appear as the final surprise guest (à la MacDonald and a crooning Ed Helms last night) when O'Brien films his last Tonight Show tomorrow.
Stern noted this week that Rosie O'Donnell offered to pay to fly him to L.A. for the guest spot and even mused that it would be "a hell of a way" to send Conan off—that is, if NBC hadn't imposed a gag order. Which really is just another reason why speculation is rampant that the parties are trying to keep the appearance under the radar.
We'd advise you to watch this space, but judging by Conan's ratings surge, we're pretty sure the nudge is unnecessary.
In the meantime, if it's balls-to-the-wall prescience you're after, look no further than Norm MacDonald, who dropped by Late Night With Conan O'Brien back in February 2009, just a week before the show's end.
"It's stunning how Jay Leno outfoxed you again," he began. "Everybody's like, 'Oh, I'm Jay Leno,' they do the voice and everything.
"Meanwhile, he's the shrewdest guy. He outfoxed—you're in good company—he outfoxed Johnny Carson, David Letterman. Every 10 years some redheaded rube shows up."
Well then, looks like Conan was right on time.
In order to bookend his knife-twisting, albeit good-natured, appearances, MacDonald made a surprise stop on The Tonight Show With Conan O'Brien (get the name in while you still can) Tuesday night, ostensibly to deliver a comically belated congratulatory gift basket for Conan's no-longer job.