Singer-songwriter Caitlin Cannon joins us for a conversation that swings between funny, uncomfortable, and unexpectedly heavy in the best way. We talk about how her songs often hide jokes inside darker truths, why meaning in her writing shifts as the story unfolds, and how learning to do less vocally completely changed the way she writes and records. Caitlin walks us through the ideas behind her album Love Addict, her relationship with faith and desire, and why some of her songs tend to make people squirm before they make sense.

Things also take a turn into the deeply personal, as Caitlin opens up about writing a song from her incarcerated brother’s perspective and how music became the only way she could tell the truth about something that big. It’s a loose, honest conversation about art, discomfort, and where songs really come from — with plenty of laughs along the way — and one that slowly reveals just how much weight can live underneath humor.

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