“The Nightfly”—second song, side two of The Nightfly (Donald Fagen) (1982)

The cover of The Nightfly LP is a theatrical photo of Donald Fagen as a late-night radio DJ, in front of his mic, smoking, crumpled Chesterfield pack, full ashtray, a record on the turntable (I can't tell what it is, though the cover is visible). There's a clipboard with possible ad copy, or station protocol. A large clock says 4:09, which we presume is A.M. The back cover shows a suburban house, lit by what could only be moonlight. A light is on in an upstairs bedroom, that you have to assume, because of a brief biographical note, belongs to the young Donald Fagen, who is listening to a late-night jazz radio station. “The Nightfly” is a funny song, beginning with such specifics, “I'm Lester the Nightfly,” followed by some radio DJ talk, all kind of unfocused, then leading into this beautiful chorus, with the backup singers: “An independent station/WJAZ”—sounding exactly like a radio call sign jingle from yesteryear. In the second verse, then, he says he's got “plenty of java and Chesterfield Kings”—but feels like crying and wishes he had a heart like ice. But then he goes into ad copy for a beauty product. By the third verse, though, it's all broken-hearted confessional, ending with “Tonight you're still on my mind.” So this song really does get that feeling, with the music wavering from kind of jittery, jazzy formlessness to the friendly, nostalgic jingle, and the DJ going from business as usual to melancholy confessional. It's nearing the end of his shift (the Bourbon's no doubt in a hidden pint somewhere), and his ex-flame is certainly not listening. Maybe no one's listening, except for, of course, those lonely insomniacs and young romantics, jazz fans, the radio volume low, so they don't wake their parents.

—Randy Russell 4.26.20