Just saying "Chris Elliot with David Letterman" should give a sense of weird enough, which is fine by me since I love his humor. But it's also offbeat because of the topic and how that relates to what came later. I don't want to give all of it away, but will just say that at the heart of it is Jay Leno. Yes, that should be clear from the image and graphic below, but it swirls in many different directions from that.
Though this is one 9-minute video, it's actually several related segments from different shows edited together. The first segment may not seem to be part of it, but it all comes around in the end.