Bill Callahan – The Man I’m Supposed To Be

14th November 2025 · 2020s, 2025, Music

Bill Callahan looks back on his life and reflects on the man he has been, and the man he’d like to be, at the age of 58.

“I saw that demon inside of me,” sings Bill Callahan over a plaintive musical backing, “Trying to claim my body as its own.”

Mid-life crisis might not be the most natural subject for a song but Callahan’s confessional ruminations on a life lived – and one that’s meant to be – are perfectly poignant.

I love the way the song starts with gentle strumming  before disintegrating into distortion he concludes with a message that will surely resonate with anyone of a similar age (or older): “Now my biggest fear is not the dying / My biggest fear is that I’ll stop trying / To be the man I am supposed to be.”

The Man I’m Supposed To Be is the first song from his forthcoming eighth album, whose theme is encapsulated in its title, My Days Of 58.