Bill Callahan is an alternative country and indie rock institution, so it is difficult to think about a time when he will no longer be around. However, Callahan‘s legacy is clearly at the forefront of his mind with his newly announced record, My Days of 58, out 27 February 2026 on Drag City In that spirit, lead single, “The Man I’m Supposed to Be”, is a call to action, a carpe diem for the advanced middle age malaise that will eventually come for us all.
The opening tone is bleak, like Richard Buckner, donning all black, with very little cause for hope. The gloomy notes open up for a brief moment to unveil the sentiment that, in the end, the kids will be fine on an imagined island (maybe some connection to global warming and rising sea levels). If they’re not, perhaps it’s for the better. Callahan kicks the music with a need to get back down to business (he is in his late 50s after all): “I’ve been living too long in my head / Not loving you enough in our bed.”
Discordant sounds enter, signaling that the next thing he knows, he will be dead. However, that is not the end, for in any thought-provoking poem, there is always a turn. It comes in palpitating fashion: “And now my biggest fear is not the dying / My biggest fear is that I’ll start trying / To be the man I am supposed to be.” His call to take life seriously becomes quite the paradox, as it means laughing in the face of death. The central meaning is brilliant on so many levels, especially when the track comes to an abrupt halt with a maniacal laugh.