A lament of grief, "Playboy Mommy" was written following a miscarriage that Amos suffered. Amos suffered her first miscarriage in December 1996 and began the process of writing and recording From the Choirgirl Hotel soon after. "Around three months, I lost the baby," she said in an interview for the Phoenix New Times in 1998. "I thought I was out of the woods and everything, so it was a really painful thing. She was a little girl, and I was really connected to her.

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