About the Artist
Anna May is a singer-songwriter based in Los Angeles, by way of Connecticut, Colorado, New Orleans, and a handful of other places she has called home along the way. Her music is folk with a jazz current she picked up during a year in New Orleans, and her songs tend to run long, closer to poetry than radio. At 15 she left public school to unschool herself in nature, reading Thoreau and writing constantly. She calls herself a PhD in Breakup Songs, and last year she released a four-part single series to back up the claim. Her newest song, Crying at Erewhon, takes a sharp turn from the rest of her catalog.
Anna May
About the Episode (Episode 143)
Anna May: A PhD in Breakup Songs
Anna May joined Jason English from under the redwoods in Mill Valley, California, sitting outside in her dad's hometown. She had just finished a run of breakup songs, started embracing makeup for the first time in her 30s, and written a new song about the worst afternoon of her year. The conversation is about what it costs to protect a creative life when everything, from social media to AI, keeps knocking on the glass.
Key Conversation Points
Fireflies, Buffalo, and a PhD in Breakup Songs: Anna writes long, and she is fine with that. On her four-part breakup series and songs that run past the three-minute rule, she says, "my songs are better than the relationships themselves."
The Emotional Greenhouse: She left school at 15 to protect the part of her that needed to write. "Being in uncomfortable situations forces you to write some of your best work," she says.
Crying at Erewhon: Dumped by text on her way into a Los Angeles grocery store, she decided the moment was a song instead of a breakdown. "I feel terrible right now, but I'm gonna write the song."
The episode closes with the question Jason asks every guest, the one about curiosity. Anna's answer is worth hearing in full. Watch the conversation below.