Chicago singer Jimmy Damon might not be a household name, but he is the only person who was authorized to sing Frank Sinatra’s songs while he was still alive. For the last 30 years, Damon has called Chicago home, and his mark on windy city culture spans far and wide. This summer, you can find Damon performing at various street festivals and Spirit of Chicago Cruises. Damon talked about what brought him to Chicago in the first place.

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Listen to an extended interview with Jimmy Damon