The White Stripes – “Fell in Love with a Girl” and “Little Room” (2002)
This is the first of these that I actually remember watching live and I remember being absolutely blown away. It’s a little more shambolic than I remember it being, but to me it’s still a good reminder of how good this band was, how much I loved White Blood Cells when it came out, and – to an extent – how i’ve pretty much had no interest in anything else Jack White has done since the band called it quits.
Warren Zevon – “Roland the Headless Thompson Gunner” (October 2002)
In 2002, frequent Letterman guest Warren Zevon was diagnosed with inoperable mesothelioma. He made his final appearence on the show in October of that year, in which he was the only guest for entire half-hour. The show ended with his final public performance, of 1978’s “Roland the Headless Thompson Gunner.” “Roland,” like many of Zevon’s songs, showcases his acidic wit, but it takes on a new tone in the light of his battle with cancer. Zevon died less than a year later in September 2003, shortly after releasing his excellent final album The Wind. Letterman and Shaffer payed tribute to Zevon on the first episode after his death, and also played his performance of “Mutineer” from this episode. You can watch Zevon’s entire final episode, complete with interviews and a few musical performances on YouTube.
Kanye West – “All Falls Down” (2004)
Note that Yeezy was so new at the time that Letterman actually introduces him as a “record producer” first and foremost. As much as I love Kayne’s other records, I still have a special place in my heart for The College Dropout and this is a really great showcase for his talents as a performer. In addition to Syleena Johnson, West is also backed by a pre-fame (by which I mean, even pre-“Ordinary People”) John Legend on piano.
TV on the Radio – “Wolf Like Me” (September 2006)
From how many times he’s had the band on, TV on the Radio seems to have become another of Letterman’s personal favorite musical guests. They performed a total of five times on the show (plus one of those Live on Letterman sets) over the past decade – pretty much guaranteed to be booked whenever they had a new record (on one occasion they performed a standalone single!). They killed it every time they played, but their best performance is still their first, of “Wolf Like Me,” in September 2006.