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Tom Ripley is a charming sociopath who inspires both love and loathing in The Talented Mr. Ripley, the first of the five-book Ripliad series. Patricia Highsmith’s most notorious character, a nefarious social climber willing to do anything to attain a life of wealth and privilege, became a blueprint for psychopathic anti-heroes from Tony Soprano to Walter White. The 1955 novel sees Tom travel to the fictional Italian resort town of Mongibello on a deceptive mission to befriend errant shipping heir Dickie Greenleaf and persuade him to come home to America at the behest of his beleaguered father, who is funding Tom’s venture. It won the Grand Prix de Littérature Policière for best international crime novel and has inspired a number of stage and screen adaptations, including the 1960 film Purple Noon and the 1999 Matt Damon-led The Talented Mr. Ripley. Highsmith would publish more than 20 novels throughout her career, including renowned titles such as Strangers on a Train, The Price of Salt (later republished as Carol), and Deep Water. But while her legacy as one of the most influential crime writers of the 20th century is undeniable, her reputation as an outspoken anti-Semite has raised questions about her troubling personal views. —Megan McCluskey

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