Disgraceland’s Jake Brennan, Songs About Shady Characters & Black Pumas


This week, hosts Jim DeRogatis and Greg Kot share favorite songs about shady characters and talk with Jake Brennan, host of the Disgraceland podcast. Plus the Black Pumas share the songs that got them hooked on music. 

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Disgraceland’s Jake Brennan


This week, Jim and Greg chat with Jake Brennan, the host of the true crime music podcast Disgraceland. They discuss the differences between "transgressive fiction" storytelling and journalism, plus talk about the myths and stories associated with musicians behaving badly.

Songs About Shady Characters

Jim and Greg highlight songs about shady and sometimes nefarious characters.


  • Erykah Badu, "Tyrone"
  • The Clash, "Wrong ‘Em Boyo"
  • The Dixie Chicks/The Chicks, "Goodbye Earl"
  • Pink Floyd, "Arnold Layne"


  • Solomon Burke, "Maggie’s Farm"
  • Nick Cave, "Mack the Knife"
  • Nelly Furtado, "Maneater"
  • Ghostface Killah, "Maxine"

Hooked On Sonics: Black Pumas


Photo by Jody Domingue

The Grammy nominated Austin duo Black Pumas shares the songs that got them Hooked On Sonics.

Adrian Quesada - N.W.A., "100 Miles and Runnin’"

Eric Burton - New Radicals, "You Get What You Give"

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