Arsenic and Old Lace (1944): Playwright Joseph Kesserling initially conceived his 1941 Broadway hit—likely inspired by a real-life Connecticut biddy who poisoned boarders for their pensions—as a heavy drama. Luckily, he realized it would fare better as a manic comedy. Although a high mark for neither director Frank Capra nor star Cary Grant, the film version is at least faithfully dark, with two adorable geriatric murders and Raymond Massey, so menacing it’s possible he never realized he was in a comedy.
Monsieur Verdoux (1947): Charles Chaplin cracked jokes about immigration (The Immigrant), the Depression (Modern Times) and Hitler (The Great Dictator). It was only natural he would make a light souffle about a serial killer. Chaplin’s anti-hero is the most charming of psychopaths, an elegant gentleman who spends the film offing wealthy widows, but only to support his children and crippled wife. But Chaplin had finally gone too far: It was his first major bomb and an inevitable cult item.
Kind Hearts and Coronets (1949): Though they produced films in many genres, Britain’s Ealing Studios are primarily remembered for the wonderfully mordant comedies they made with Alec Guinness. Here, an amoral schemer (Dennis Price) hoping to inherit a dukedom murders the eight people standing in his way, all played by Guinness (including a feisty Suffragette). Later came The Ladykillers (1956), in which a gaggle of thieves try and fail to murder a granny.
Pretty Maids all in a Row (1971): An insane teaming of Barbarella’s Roger Vadim and Gene Roddenberry turns more insane still with excellent stunt casting: Rock Hudson, exhibiting crack comic timing and a porn mustache, plays a high school gym teacher who, while coaxing a sexless nerd on how to be a stud, gleefully beds and then offs the school’s bevy of hot young babes.
Grosse Pointe Blank (1997): The post-Tarantino wave produced piles of dreck, but they also birthed George Armitage’s sharp rom-com, in which the lovelorn hero (John Cusack, rarely better) is also a paid assassin who can kill with a pen.
Horrible Bosses (2011): Strongly suspecting, in this tamer era, Bateman, Day and Sudeikis will wuss out on murdering Spacey, Aniston and Farrell.