"The Bengalee alone who is unfitted by physical disqualification for a constable, makes in this country the perfect detective” (The Annual Police Report of Calcutta of 1855)1 From the onset the detective is asserted as not just another man, his skills, mettle and personality sets him apart from the reader. The thrill and excitement that is integral to the genre creates the competitive sphere where the reader engages with the puzzle with the intention of solving it before the super intelligent man. This distance is often bridged by awe and aspiration. For the detective, therefore, it is imperative that he becomes inspirational and upholds the incredible feats as credible at the same time. This is when I argue the characterization of a detective becomes of supreme importance. He must not only stand for the imagination of a Bengali who can be identified with, but also account for his awe inspiring characteristics and his impeccable road to success. For the Bengali, this was an area which captured the reader’s imagination on the onset; thankfully we had the police reports created by our superior colonial masters attesting to the fact that we always already had it in us and in the historical reality of colonial capital Calcutta such a figure became social presence. Thus it was just a matter of a proficient pen to capture such a figure and by incredible bouts of eulogizing and narrativising, to create in Bengali literature a genre which has been both popular and successful at the same time. This paper traces the penetration of a cultural and social real into pages of literature and studies the evolution of the detective from a mere man to a super man of reasonable capabilities. Keywords: Crime fiction, Detective literature, characterization, Masculinities, Gender roles, Colonialism, Holmes, Subversion, appropriation.