When it comes to being rich without any effort, no one is better than Henry Graham (Walter Matthau), a very wealthy man who has never worked a day in his life, living off his vast inheritance and wasting his fortune through his excessive tendencies. However, this can’t go on for much longer, as he soon discovers that he has completely run out of money, and without any hope of salvaging his fortune through any simple means, he contemplates just ending his life. This is until he realizes there is an easy way out of this predicament – he needs to find a wealthy single woman without any heirs, marry her and subsequently kill her, inheriting her fortune and once again taking his place amongst the upper-class elite. He sets his sights on Henriette Lowell (Elaine May), a timid botanist who makes up for her social awkwardness with her vast fortune, most of which she doesn’t know what to do with. An extraordinarily gullible woman, she falls for Henry’s charms and believes his professions of love are authentic, not realizing that beneath his veneer of passion sits a very sinister motive. Those around her start to warn Henrietta about her suspicions, not realizing that Henry is one of the most cunning people they’d ever hope to meet, and is more than capable of getting himself out of any situation – and nothing will deter him from achieving his goal of bringing an end to Henrietta’s life so he can resume his own comfortably.

A New Leaf has become one of the most definitive comedy films of its era, a wonderfully dark satire about the upper-class, told through the perspective of two people sitting at the very top of the social ladder. Written and directed by Elaine May, making her directorial debut in what would prove to be one of the most impressive introductions to filmmaking of its era, she makes exceptional use of her background in comedy to deliver one of the funniest films ever made. A New Leaf has many components that needed to be executed with deft precision and a lot of meticulous care, but considering the director was willing to submerge herself into the experience results in a daring and subversive comedy that is both outrageously hilarious and hopelessly bleak, the perfect combinations of both the broad vaudeville that May was well-versed in, and the shift towards more sinister stories as a result of New Hollywood, where we films could position reprehensible characters in the central roles, and not have to resolve to any sort of redemption. In all honesty, May’s first film is also her best, and while she would go on to do very good work in The Heartbreak Kid and Mikey and Nicky, she never again reached the incredible heights she did here, with everything about A New Leaf being so well-composed, you’d find it almost impossible to find a more perfect comedy – perhaps not received as the defining comic masterwork that it deserved at the time, this film has aged incredibly well, and is just as uncomfortably brilliant as it was nearly half a century ago.

Perhaps we can say this is a result of my bias, but I’ve never met a Walter Matthau performance I didn’t adore – whether lead or supporting, hero or villain, charlatan or lovable rogue, he was consistently great in everything he did. The problem with a career like Matthau’s is that his output was so regularly terrific, it’s almost impossible to form a consensus on what his best film actually was. A New Leaf is one of many that can legitimately contend for the position, as not only does it allow Matthau to show off his unique comedic talents, he also occupies a very different role than he normally does. No longer the endearing everyman he perfected over the years, his performance as Henry Graham is a masterwork of comedic ingenuity – playing the character with a combination of hubristic charm and detached disdain, he perfectly captures the upper-class malaise this film is so potently satirizing. Matthau’s performance is contrasted by that of May herself, who occupies the other central role of Henrietta, the milquetoast botanist who finds herself captivated by the charms of a man who claims to love her, not realizing that it is all a ruse to further his own status and get himself out of a difficult situation. May hasn’t always gotten the credit she deserved as a comic hurricane, someone whose sensibilities never wavered throughout her career, and while her output over the years started to wane as she gradually faded from public view, whenever she did work, she was always tremendous. A New Leaf was a passion project for May, and it’s difficult to imagine anyone playing the role of Henrietta more brilliantly than her.

Moreover, the dynamic between Matthau and May is so entertaining, as both are at the very top of their comedic game, and managed to take one-dimensional roles and turn them into memorable characters. This is one of the most notable successes in A New Leaf – despite being quite absurd, and often wholly unrealistic towards the beginning, there is a sense of authenticity underpinning this film. The emotions are real, the humour broad but still nuanced enough to not surrender itself to chaotic disorder in the same way other comedies at the time were thriving on. May’s intention with this film was to make a perfectly human story through the guise of an outrageous comedy, which is something she demonstrated in her subsequent career, where even at its most unbelievable (talking to you, Ishtar), there was a sense of cohesion in how the director approaches her stories and builds her characters – perhaps influenced by stock figures (a byproduct of her on-stage career, where a lot of her work with Nichols involved drawing from a set of pre-existing character tropes), but infused with a lot of gravitas and reality that prevents them from ever being entirely cliched or predictable. The dynamic that governs this film is one that was always going to guarantee success – the scheming playboy seducing and plotting to kill the wealthy bride, who just so happens to be extremely socially-incompetent, had the formula for success from the outset. Yet, the film goes beyond archetype, and delivers a twisted satire that does something too many contemporary satires neglect – it allows us to become invested in the characters, not only their part in a subversive story.

What makes A New Leaf so effective is that despite being quite dark – it is essentially about an opportunistic sycophant taking advantage of an innocent woman and plotting to kill her – the film is never mean-spirited or unnecessarily cold. May has a distinct warmth to her style, both narratively and visually, which is why this film is such a conundrum. Based solely on the story, it should be an acidic dark comedy without much optimism. Yet, it’s still a very sweet and endearing film that takes the form of a true romance, where by the end of it, we realize we haven’t merely been watching a tale of a man trying to restore his status, but of two people secretly falling in love. The ending of A New Leaf had no business being this upbeat and charming, and perhaps this is why its such a brilliant film – it takes the form of a very unconventional romance, one where the motives behind it are very much known and as far from endearing, but there’s still a strong undercurrent of passion. The realization that Henrietta was far more than just a wealthy woman to be taken advantage of, but rather the impetus for Henry to actually start making an effort, was a tremendous moment, and the point in which the audience knows that what we’re watching is extremely special. There’s a certain empathy in this film that doesn’t necessarily pervade the more cynical overtures but complements it well enough to create a unique blend of bleak and hopeful moments.

Elaine May has been tragically undervalued throughout her career, and despite being a comedy icon, she was a revolutionary filmmaker as well, a stalwart of female-led cinema that could be bold, audacious and outright hilarious. A New Leaf was her first film and stands not only as her best but as one of the most original comedies of its era. The story itself may be inspired by many earlier comedies that dealt with the tricky subject of murder (there are slight traces of Kind Hearts and Coronets and Arsenic and Old Lace peppered throughout the film), but the execution is entirely unique – sentimental without being overwrought, and featuring a delightful comedic melancholy that helped define this era of filmmaking, where broad concepts were filtered through the lens of emotionally-resonant stories. By no means a saccharine or predictable piece (it avoids cliche entirely, and is capable of being remarkably ahead of its time), A New Leaf is just a self-assured, lovable comedy with moments of revelatory brilliance, terrific performances and a hilarious story that manages to make some truly horrifying ideas not only very funny, but also hopelessly enthralling. Many filmmakers looking to make subversive films can take a cue from A New Leaf, a film that seems so at ease with its own brilliance, it never needs to make a show of it.