Stool Pigeon Saturday - Samuel on Diamond Tooth Lil
From Behind Gray Walls by Behind Gray Walls
February 14, 2026 · 44 min
About this episode
Samuel tells the story of Diamond Tooth Lil, a dance hall girl and madam, and her relationship with gunslinger Diamondfield Jack.
In this Valentine’s Stool Pigeon special, Samuel tells the story of a great Western romance. We follow Diamond Tooth Lil, who found work as a dance hall girl, a singer, and eventually a madam. Through her travels, Lil earned fame for her beauty and charm—but she also stole the heart of gunslinger Diamondfield Jack (Jack Davis #820). Through their relationship, we gain a perspective on one of the penitentiary’s most notorious prisoners in a way we’ve never had before. Join us for a story of heartbreak, longing, and enduring love you won’t want to miss.
People in this episode
Host: Samuel
Topics covered
- Western romance
- dance hall girls
- madams
- notorious prisoners
- heartbreak
- enduring love
Keywords
- Valentine's
- fame
- beauty
- charm
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