Ripliad

Patricia Highsmith wrote this series of novels about Tom Ripley. The Talented Mr. Ripley, Ripley Under Ground, Ripley's Game, The Boy Who Followed Ripley and Ripley Under Water are a chronicle of a charming and utterly sociopathic man. All evidence much black humor, and are notable as inverted mysteries in which Ripley always gets away with his crimes in the end.

The labels Affably Evil, Heroic Sociopath and Villain Protagonist describe Ripley well, and every novel after the first invokes Villains Out Shopping by depicting Ripley's affluent life in the French countryside, beloved by his servants and engaging in artistic pursuits. Ripley is also somewhat Ambiguously Gay (or rather, explicitly states he just doesn't know what he is), although it could be argued that, like Dexter, he is simply a rather warped Chaste Hero, having difficulty forming any kind of relationship given his psychological problems.

Other tropes used in the series:

 * Alter Ego Acting: In The Talented Mr. Ripley, Tom is able to both convincingly take Dickie Greenleaf's identity, and portray an exaggerated version of himself before the same police officers who saw him as Dickie and get away with it.
 * Cut Himself Shaving /GoodScarsEvilScars /RedRightHand: One of Ripley's criminal contacts is a gangster, Reeves Minot, whose handsome features are marred by a nasty scar on his face, which he attempts to explain away with various unconvincing stories.
 * Dead Artists Are Better: Played with in Ripley Under Ground, in that it features Ripley as part of a scam to produce further works of an artist unsuccessful in life who killed himself at a young age, and Ripley ends up masquerading as the artist.
 * Devil in Plain Sight: Ripley is a version of this from the second book onward, as he has a lot of suspicion attached to himself but no one has ever been able to pin any crimes on him.
 * Dorian Gray: Found in Ho Yay moments.
 * Even Evil Has Standards: Ripley tries to avoid killing people unless absolutely necessary, first trying to get them to cooperate with his schemes. The only people he ever kills without any guilt are some gangsters in Ripley's Game.
 * Ripley Under Water has this as a major part of its Evil Versus Evil plot, where Ripley's peaceful life is threatened by a nasty Inspector Javert who is a wife-beater and ugly American who while ironically on the side of good (he tries to expose Ripley's murders), is mostly interested in the sadistic pleasure in hurting others.
 * He never feels any guilt for killing Freddie in the first book.
 * Freudian Excuse: Ripley was an orphan brought up by his emotionally abusive aunt.
 * Funetik Aksent: used for all of the French characters who call Ripley "Tome".
 * Sociopathic Hero
 * Idiosyncratic Episode Naming
 * Inspector Javert: Ripley often is dogged by someone on to his crimes, but if they're police will ultimately escape them, and if not, likely kill them.
 * Ivy League for Everyone
 * Karma Houdini: Except for the film 'Purple Noon', where he just barely misses pulling one of these off.
 * Unreliable Narrator: While the books are narrated in third-person, everything is essentially from Ripley's perspective as he has the Sympathetic POV, and thus his reasonings for his various crimes are presented as legitimate.