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Chicago residential novelist Dan Dark (Robert Downey Jr.), crippled by a horribly severe case of psioriasis, starts rewriting his 1950s noir novel "The Singing Detective" in his mind in a desperate effort to hang on to his sanity. Becoming the title character himself, he heads off in pursuit of Nazis in the 1940's who serve in place of his own personal demons. With the help of eccentric psychologist, Dr Gibbon (Gibson), who uses the book as a road map into the Dan Dark's psyche, he slowly liberates himself from the trauma of his childhood.
This is the story of a sensitive teenager, Leland (Ryan Gosling), faced with issues of morality and hope under difficult circumstances, who is arrested and sent to juvenile hall, after he kills an autistic child out of sympathy. Once there, he meets a teacher, Mr. Pearl (Don Cheadle), who helps him figure out the reasons for why he committed the crime, as we also see the ramifications of the murder have on his community, his family, and that of the victim.