Broken Record with Rick Rubin, Malcolm Gladwell, Bruce Headlam and Justin Richmond Loudon Wainwright III
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Sep 2, 2025 
Loudon Wainwright III, a Grammy-winning singer-songwriter, shares his journey through over five decades of music. He discusses his candid songwriting, often infused with humor, about family life and personal struggles. Wainwright reflects on his privileged upbringing and the electric feeling of performing live for the first time. He recounts collaborations with Richard Thompson and delves into the emotional depths of his songs—balancing nostalgia, loneliness, and creativity, showcasing how his past profoundly shapes his music.
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Crafting A Distinct Stage Persona
- Loudon adopted his boarding-school Brooks Brothers look to stand out in the 60s folk scene.
- He leaned into his upper-class background and wrote truthfully about it instead of inventing a false persona.
Channel Competition Without Self-Destruction
- Use competitiveness as a motivating engine but monitor its cost.
- Let it spur you to better work while avoiding isolation and family damage.
Journalistic Clarity Shapes Songwriting
- Loudon credits his journalist father for his song structure and clarity.
- He writes with beginnings, middles, and ends and carries a Filofax to capture ideas.