Remember That Time Howard Stern Went On Letterman And Absolutely Destroyed Jay Leno?

Today is David Letterman’s 68th birthday, and to celebrate, let’s recall one of his most memorable interviews of all-time: Howard Stern. Now, Stern has done Letterman’s show quite a bit over the years, and there’s plenty of appearances we could focus on, but let’s look at one even-more-memorable-than-usual Stern-Letterman interview, when Howard decided to absolutely tee off on Dave biggest rival, Jay Leno.

In 2011, the Second Late Night War was over. Leno was back in his 11:30 slot, Conan had moved to TBS, and Letterman had watched the whole thing unfold with a great big smirk on his face. No one was really thinking about it at this point, but that didn’t stop Stern from bringing it up in the most hilariously awkward way possible.

As soon as Stern comes out, he says “I wanna see you beat Jay Leno in the ratings tonight,” making it quite clear the direction he was about to take things. After mentioning that he read Bill Carter’s book The War For Late Night and “studied it like the Torah,” Stern moves in for the kill, proclaiming that “you know, as well as everyone in this room, Jay is horrible, right?” Letterman doesn’t echo his sentiment, but he doesn’t necessarily disagree either. Stern goes onto to criticize Dave for his Super Bowl commercial with Leno, and makes fun of Paul Shaffer for “getting high all the time.”

Of course, brutal honesty is pretty much Howard Stern’s calling card. Even if you loathe him for some of his more controversial statements, it’s hard not to admire his willingness to say precisely what’s on his mind. In this case, it was his raw contempt for Dave’s biggest competitor. You get the strong feeling that throughout the interview, Stern is desperately trying to get Letterman to say he hates Jay Leno. Letterman doesn’t actually admit this, but his silence might say it all.

Throughout the interview Stern talks far more than Letterman, which Letterman references at one point, joking that he “didn’t really need to show up tonight.” And while Stern seems staunchly pro-Letterman, he’s an equal opportunity offender, and he relishes in the chance to mock Letterman for his 2009 sex scandal, about which he jokes “Dave’s finally having some fun at work.”

Stern is one of Letterman’s most popular guests, appearing on his NBC and CBS shows over 20 times, and it’s not hard to see why. His blunt honesty always make things interesting. The key here is that Letterman is usually the brutally honest one. We’ve seen this in famous interviews like the time he told Bill O’Reilly that “60 percent of what you say is crap,” or when he had Paris Hilton on and refused to humor any of her silliness. Unlike, the kill-them-with-kindness approach Jimmy Fallon takes, Letterman has always gotten a kick out of making them squirm.

Howard Stern is the one person who can make Letterman squirm, and it makes for brilliant television.