Is David Letterman Ready to be Done with the Late Show?

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Put two misanthropic comic geniuses in a room together, the results are bound to be interesting—and Howard Stern’s visit to the Late Show on Thursday night was no exception. In a wide-ranging exchange that covered everything from chess to their mutual hatred of Jay Leno, Stern did what he does best, hijacking the conversation with a disarming lack of tact. But was Stern serious when he suggested that Regis Philbin has been fired from LIVE!? And was Dave serious when he said the next two years would be his last on the air?

Stern made it clear from the get-go he was disappointed in what he deemed to be a “complacent” attitude among Team Letterman when it came to the business of crushing Leno in the ratings.

“You had your foot on his neck,” Stern admonished Letterman, referring to the 2010 Super Bowl ad that placed the Late Show host on a couch just inches away from his nemesis. “What was that? I didn’t like it...I don’t acknowledge my competitors.” He had a point. It was a popular promo, but it undercut the vicious attacks on Leno’s character that were dominating Dave’s monologues around this time last year. (The themes are still prevalent. Just the other night, Letterman wondered out loud if Egyptian President Hosni Mubarak would indeed step down, or wind up “pulling a Leno.”)

“I love you. I am in your corner,” Stern pledged, eliciting a fist-bump from Letterman. “I don’t want the same thing to happen to you that happened to Regis.” This elicited a big laugh from Dave and the audience, but Stern pressed on, making Letterman uncomfortable. “You know, he was fired. He lives in my building... He got fired. He asked for more money and they gave poor old Regis the boot.”

Stern, a former CBS employee when he still worked in terrestrial radio, made a funny and valid point about his contentious relationship with the company: “I watch what’s going on. You had your scandal. Charlie Sheen has his scandal. They keep hiring you guys. Me, I get fired. They took me to court and sued me. What did I do wrong? I mentioned where I work.” (He was referring to a 2006 lawsuit against him and Sirius radio for having promoted his new satellite show on their airwaves.) Stern credited Transcendental Meditation with helping him avoid the porn star-strewn road not taken.

Dave tried valiantly to change the subject to Stern’s new Sirius deal, rumored to be worth even more than the $500 million contract he signed with them in 2005. But once again, Stern (now 57) turned the tables on Dave (now 63), asking the host, “How much longer are you doing this?” To which Letterman replied: “Maybe two years, I think?”

Johnny Carson was 67 when he finally stepped down from The Tonight Show, so Letterman’s retirement timeline seems right. But the man is as sharply funny and ornery as ever. I know I'll miss him when he's gone. Will you? And what did you think about Howard’s visit? Too much, or just enough?

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