Shadow of a Doubt (1943): Fritz Lang’s M (1931) featured a cinema first: a psychopath who was borderline sympathetic. But Peter Lorre’s child killer wasn’t exactly likable; he did kill children, after all. Neither is Joseph Cotten’s “Merry Widow Murderer” in this Alfred Hitchcock masterpiece. But at least someone loves him: his niece Teresa Wright, who’s ecstatic when Cotten pays a visit to her boring American town, unaware he’s really just eluding capture.
Arsenic and Old Lace (1944): What are two adorable old spinsters doing poisoning lonely old men with laced elderberry wine? Cutest serial killers ever.
Monsieur Verdoux (1947): For his second talkie, Charlie Chaplin ditched the Tramp in favor of a less immediately lovable, but no less adorable creation: a fey, elegant character who marries wealthy widows then plots their death. But why? All to put food on his family’s table after he loses his job in the 1929 stock market crash.
A Shock to the System (1990): A longtime executive (Michael Caine), tired of being passed over for promotion, plots the violent murders of all those who have wronged him. In the Andrew Klavan source novel, Caine’s character is brought to justice and the world is set aright. Not so in the movie. Here is one of the very few times when an unapologetic killer not only gets away with it but does so without remorse.
Grosse Pointe Blank (1997): At the height of the Tarantino deluge, when lovable hitmen were all the rage, John Cusack popped up in the trend’s most novel concoction: Lloyd Dobbler at his high school reunion, offing people. How many romantic comedies feature a lead who’s not above coldly dispatching a heavy with a pen to the jugular?
The Talented Mr. Ripley (1999): Patricia Highsmith’s Tom Ripley tended to be obliviously amoral, unlike Matt Damon’s incarnation, who’s so socially awkward and insecure his murders almost seem justified—snap judgments that, unfortunately, have to be done.
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