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The Heartless Bastards' story starts in Dayton, Ohio, where Wennerstrom found the name on a multiple choice video trivia game at a bar. As a songwriting teenager during a time when Guided by Voices and Brainiac were packing local bars and three of The Breeders were still in town, Wennerstrom used to sneak into clubs to check out the scene. "I would just see those people—my music heroes—hanging out at the bar like everyone else," she remembers. "I could see myself in them. It gave me inspiration to do my own thing."