Oh hell -- most of you youngsters won't even know who David Letterman was, but that's a separate issue.
In any case, that's a Creative Zen Nano mp3 player -- a birthday present a friend gave me in the early 90s, as I recall -- that was essentially a flash drive, with a built in volume control and LED readout, that stored approximately 200 songs in various digital formats. I loved it, not least of which is because you didn't have to worry about charging it on your computer; you could just pop in a AAA battery and you were good to go.
Bottom line is, I recently found that gadget in the back of a drawer somewhere, and was delighted to discover that it still worked like a charm. More to the point, I was listening to it yesterday, because the playlist was a snapshot in time of the music I dug in the past but -- alas -- the title readout was so small and I'm so old geezer blind I couldn't really figure out who this one of the songs was by when it popped up. Obviously, it was a cover of The Byrds' version of Bob Dylan's "My Back Pages," which struck me as relevant to that Byrds tribute album I'm producing, but I couldn't quite place who it was by or where it was from.
Fortunately, a trip to Amazon provided the solution -- it was Marshall Crenshaw from this 2006 compilation album I had totally forgotten ever having owned.
BTW, you can still get a copy of that CD to stream at the aforementioned Amazon OVER HERE. The identical mp3 player can also be found over at eBay for a paltry 35 bucks.