Oh, I used to love watching the Jay-Walking segments! My favorite was the one who tried to explain to Jay why you couldn't circumnavigate the globe, and, with the visual aid of an actual Rand-McNally globe, proceeded with an explanation that was as absurd as it was hilarious. (Apparently, he was of the belief that some of the illusionary markings, such as the Equator, were actual physical boundaries.) What was worse, was the girl who was with him when the question was originally posed suddenly understood what he was talking about and agreed with him, which only dumbfounded Leno all the more.

I wish I could find a Youtube of that particular sequence.