I'm often asked why I love Letterman by non-fans. They either don't get his humor, don't appreciate it, or liked Leno instead (uhg).
Joshua Rothman has written an excellent piece about David Letterman which aptly sums up my reasons for loving him. On his interview style:
Perhaps because it never leaves the real world behind, Letterman’s show isn’t always inventive enough to be truly side-splittingly funny. The upside, though, is that the show is often surprisingly real. Letterman is the best interviewer on late-night TV, for example, because he seems not to believe in the idea of celebrity (his own or anyone else’s). When he interviews famous people he doesn’t respect, he’s openly judgmental and censorious (he refused, for example, to talk to Paris Hilton about anything other than her time in prison); by the same token, when he interviews people he admires, like Tina Fey, his respect is palpable. (“Our first guest is an exceptionally talented and funny woman,” he said, introducing Fey, with great seriousness, earlier this year. “You can’t overstate this.”) Sometimes he lapses into respectful silence. On the other hand, when he’s angry, annoyed, impatient, or exasperated, he can’t hide it. Today’s comedy is fascinated by awkwardness, and comedians like Zach Galifianakis and Ricky Gervais excel at creating elaborate spectacles of squirm, but the awkwardness is almost always staged, and therefore toothless. Letterman’s interviews with Lindsay Lohan, Madonna, and Bill O’Reilly are actually awkward, because Letterman’s real personality is engaged. His sense of decency prevents him from keeping it light. Faced with Lindsey Lohan, he can’t bring himself to talk about “Scary Movie 5”—only about rehab. Faced with Bill O’Reilly, he can’t feign respect, or put on the airs of a serious political commentator; he can only be honest, telling O’Reilly, “I have no idea what I’m talking about, but I don’t think you do, either.”
Go read the whole thing.