Philip Marlowe

Main character of Raymond Chandler's mystery stories.

Marlowe is a rough private detective whose path usually crosses those of the upper class and big city gangsters and mobsters
He is extremely sarcastic and very used to being beat up. He once worked in the DA's office, but was fired for Insubordination

Butter wouldn't melt. The quintessential cool cat of the detective world - sharp, hard and smooth with the ladies.

Also the very un-cool protagonist of Dennis Potter's immortal TV miniseries, The Singing Detective; cursed with the name, he hallucinates about playing the game while in hospital with a debilitating bout of psoriasis.