I graduated from stories-on-tape on the first night of Chanukah in 1995, when my sister gave me my first real album—Madonna’s The Immaculate Collection on cassette. I was 10, and at 14 years my senior, my sister was part of the Madonna generation, but this wasn’t something I registered until much later.

Getting your first album—your first encounter with musical pop culture—has to be one of the most definitive moments in a girl’s childhood. For me, the Madonna cassette represented a new grown-up connection to my sister. Everything before—games, stuffed animals, books—had marked the differences between us. While I couldn’t wear the same clothes and makeup as her, I could at least now listen to her music.