David Letterman called one of the Late Show employees and asked her what she had been doing. When she mentioned that she was listening to music, he asked her if she was listening to Jimmy Buffett, because apparently he knew she was a fan. She said yes, he then pressured her into singing one of the songs, to which she sang a line from “Volcano”… “I don’t know…I don’t know…I don’t know where I’m a gonna go when the…” To which Dave said “Okay, that’s enough.”
For the next 4 or 5 minutes Dave sang a line from “Come Monday” and Paul Shaffer played a bit of the song.