I wanted to post this interview for quite a while but it wasn't up anywhere. It's a terrific interview and a terrific return to the "old style" of Letterman political interviews.
I knew that Rumsfeld had been the oldest Secretary of Defense but I had no idea that he had been the youngest as well. And likewise that he had known, interacted with and served for so many U.S. Presidents. A fascinating interview and includes some great "mule" banter.
Segments like this one are one of the main reasons that Letterman is (has been) head and shoulders above every other talk show host. When bringing on political or polarizing figures, he isn't content to be apolitical and have them tell stories about how they love their cat (as other talk shows will do). Instead, he does the opposite - mixing the jokes with direct questions about the important matters of the day. At times like these the show ceases to be just a dumb comedy show and gains an edge of serious journalism.
And the BEST part of the serious political interview segments was that it was entirely detached and objective. When someone from the left was on, for instance, Letterman would ask fair but hard-hitting questions. When someone from the right was on, it was the same deal. Again, in the vein of journalism, the questions would be fair but tough regardless of the guest. This was probably most evident during the presidential campaign of 2000. The "Late Show" were able to book both presidential candidates and the reviews on both interviews were that Letterman had actually been harder-hitting than most interviews done by the "serious" journalists.
Unfortunately all of this is filed under the "old style" above because recently things have changed. Though THIS interview is recent and that shows Letterman is still capable of doing it, lately he's become much more politicized. He'll give guests from the left a free pass and say things to those on the right are treated with outright hostility. Recently in an interview with Rand Paul for instance, Letterman actually uttered the phrase, "You know, I think he’s wrong about some of these things. I just can’t tell you why.” It's a statement so dumb, I couldn't (and can't) believe it was said.
All the more reason to enjoy interviews like these because they're an endangered species.