Angel from Montgomery

John Prine would often assume a character for his songs and sing them in the first person, even if that character is a woman. "Angel From Montgomery" begins: I am an old woman named after my mother The woman in the song is looking for meaning in her life, which has gotten quite dull. She dreams of turning into an angel or becoming a rodeo poster - anything that could make her feel special. Prine had no misgivings about assuming a female character. As a writer, he felt he could be any gender.

Prine got help writing this song from his friend Eddie Holstein. They set out to write a song together, and Holstein suggested it be about old people, similar to another song Prine wrote called "Hello In There." Prince didn't want to do that, but hit on the idea to write about "a middle-aged woman who feels older than she is." "I had this really vivid picture of this woman standing over the dishwater with soap in her hands and just walking away from it all," Prine said in the book More Songwriters On Songwriting. "I just kept that whole idea image in mind when I was writing the song, and I just let it pour out of that character's heart."

Prine was working as a mailman when he wrote this song. After doing two years in the Army, he took the job and loved it because he could think up songs while walking his route. The track appeared on his first album, which made him a star in the Chicago folk music community.