Walter Matthau plays Henry, an entitled man-child who squanders his trust fund taking his Ferrari into the shop after every time he drives it, wearing tailored suits, and having his butler take care of his every need. After he loses all his money with no other financial prospects, he does what any self-important ex-rich playboy would do and decides that he will marry a rich woman and murder her. Elaine May (who also directed the film) plays Henrietta, a plain-Jane botanist with an immense fortune and no interest in spending any of it. She is clumsy, uncultured, and infantilely clueless. Henry, seeing Henrietta as the perfect target, woos and marries her. With a synopsis like that A New Leaf seems like your typical straightforward black comedy where you’re lead along the entire film wonder if he will or won’t kill her, and in a way it is. Although much of what would be considered straightforward here seems actually more like subversive satire. Henrietta doesn’t get a makeover that involves removing her glasses. Henry doesn’t gain more affection for her and have a change of heart. They both just end up being frustratingly useless enough to deserve each other.
Henrietta is such an endearing character, before you find out how helpless she is. Her only dream in life is to discover and name a new species of fern. May shines as a clueless nerd, with the awkward muttering and the soft exclamations of, “Oh, heavens.” I, being a little bit of a clueless nerd myself, loved every awkward outfit, the bizarrely fitted hats, drab cardigans, and huge framed glasses. She is the perfect incompetent foil to Henry’s scheming, manipulative brooding. But eventually you realize she can’t even button her own shirts right.
A New Leaf is told mostly from Henry’s point of view. There’s a lot of handheld shots, grotesque close-ups from his perspective, and even a dream sequence. Though we’re constantly viewing everything from his side, we’re never expected to sympathize. If anything it only exaggerates his insufferable jackassery. Though, there is an interesting thing this movie brings up from his side: there seems to be some sort of underlying gay subtext. He is horrified at the idea of women. He’s never been married. There’s many jokes about the fact that he would even consider marriage. It’s a shame it’s played as a joke.
Elaine May had her own cut of the film that ran 180 minutes long. It was taken and re-edited to it’s released length of 102. The original cut of the film may not exist any more, so there’s no telling if the extra length added to the kooky absurdity. As it is, A New Leaf is one of the most warm and charming black comedies I’ve seen. It’s an awkward story about how two differently awful people deserve each other.