The world has lost the legendary Bobby Caldwell. More than just a futuristic and soulful singer/songwriter, he was also the greatest Sinatra interpreter of his era. This week, we pay tribute to his life - from the strange original songs that made him a superstar in Japan during the City Pop era, to his stunning Sinatra-inspired recordings and the legacy he left for subsequent generations in hip-hop, vaporwave and neo-soul.

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