Two individuals cross paths quite unexpectedly and are launched into a situation where they find themselves unable to resist committing crimes, as well as falling deeply in love through the process. Dennis (Anthony Perkins) has recently been released from a psychiatric hospital, where he has been residing for several years after committing an act of vengeful criminal arson. Sue Ann (Tuesday Weld) is a precocious high-school cheerleader who finds the sudden arrival of this mysterious man quite alluring, and when he forces himself into her life, she cannot quite resist the enticing offer he makes, where he claims to be a CIA agent deployed into this small Massachusetts town to conduct a series of tasks. He successfully convinces Sue Ann to join him in his mission, and she willingly accepts, only because he’s offering her a chance to escape the relatively dull suburban life she has grown accustomed to. However, their activities grow increasingly sordid, and soon venture into criminal territory – and suddenly caught between the prospect of returning to prison, but also the excitement that comes when committing these crimes, Dennis finds himself thoroughly conflicted, and the excitement emanating from his new companion doesn’t do much to deter him from taking the wrong path again. Very soon, they’re approaching the point of no return – and it becomes very clear that neither of them intends to turn back anytime soon.

Pretty Poison is a remarkably interesting film for a number of reasons – occurring between two of the most iconic films that sees a pair of lovers on a crime spree, namely Arthur Penn’s Bonnie and Clyde and Leonard Kastle’s The Honeymoon Killers, Noel Black’s film is a terrific adaptation of the novel by Stephen Geller, a daring and provocative dark comedy that subverts many common themes present in this niche but strangely omnipresent genre while remaining as fresh and exciting as any other highly original crime film. Black, a director whose work didn’t always receive all the attention it deserved (most likely a result of him being mostly restricted to television, where he helmed episodes of many of the greatest shows of their era), manages to compose a dreamlike crime film that borrows liberally from many genres, infusing this memorable story with healthy doses of comedy and romance, and even inserting a touch of acidic social commentary to the fray, in which the film is able to investigate some of the more interesting quirks about the counterculture era and the role of heteronormativity and the nuclear family, while never being entirely overwrought about it. It’s a complex, but outrageously entertaining black comedy that features tremendous performances, an excellent script and a premise that feels like a romantic comedy as written by Franz Kafka – and if that isn’t enough to sell you on the brilliance of Pretty Poison, absolutely nothing else is.

What is most remarkable about Pretty Poison is how singular it is in terms of its intentions, while still managing to be a wide-ranging satire that touches on many challenging themes without ever becoming excessive or too overwhelmed by the underlying social commentary. The story of a man who demonstrates clear tendencies towards irrational behaviour, no doubt brought about by some underlying mental illness, is dealt with in such a sincere and empathetic way, which seems to be contradictory to the more flippant premise of the film, creating quite an unusual dynamic between the overarching story and the means through which it goes about exploring some of the more subtle concepts that pervade throughout it. It’s a memorable excursion into the minds of two very different characters, drawing inspiration from both the source material and real-life instances of crime sprees, using the more common themes to its advantage, insofar as it attempts to present us with another kind of crime film that is less involved with the motivations or the act itself, but rather the perilous aftermath, particularly from the perspective of someone trying desperately to remain on the straight and narrow, which proves to be far more difficult. Pretty Poison says a lot more than its relatively effervescent appearance would lead you to believe, and while the audience may be enticed by seeing two of the more underrated stars of the era acting across from each other (in what would be their first of two collaborations) in this upbeat subversion of a popular genre, its the lingering sense of existential dread that draws you in and leaves you thoroughly invigorated.

Pretty Poison is a film that may unfortunately struggle to find its voice, particularly because it sometimes feels a bit too scattered, caught somewhere between an outrageously dark comedy, and a bleak crime thriller, grasping at both genres in a way that sometimes betrays the more fascinating insights the film clearly has, but which don’t always manifest in a particularly effective way. However, this doesn’t distract from the many merits that Black brings to the film – just consider how he derives some terrific performances from these actors, while still managing to tell a compelling story, which touches on broader themes in unexpectedly brilliant ways, often being able to charm us by doing very little other than maintaining its fierce conviction to the inherent strangeness of this story. Some may view Pretty Poison as being entirely implausible and perhaps even too far-fetched to be truly embraced – but the film presents a great counter-argument by way of how it toggles the relationship between reality and fiction, particularly through the character of Dennis, who seems to be in a perpetual state of confusion, where he is living within a world of complete fantasy, and in which the rest of his life seems to fall by the wayside in his endeavour to make his inner thoughts authentic, no matter how implausible they may be. In many ways, this is a perfect embodiment of the concept of the truth often being stranger than fiction, which is a genuinely effective way of looking at Pretty Poison as less of a mindless dark comedy, and more as a profoundly fascinating meditation on the nature of the criminal mind, and the aspects, whether innate or conditioned, that drive them to lead lives of debauchery.

Some have commented that Pretty Poison is a warped version of The Secret Life of Walter Mitty, an apt comparison, particularly considering how this film shares the qualities of focusing on a relatively harmless young man who is in a permanent daydreamlike-state, which he uses as a mechanism to manage his own insecurities and inability to function normally. Where this film differs is in how, instead of presenting us with a lovable rogue, we’re instead introduced to a relatively despicable character, but one we cannot help but empathize with in some way. It does help that Dennis is played by Anthony Perkins, who had become a lasting element of the cultural consciousness as a result of his work in Psycho, which also served to be something of a challenge for him, as he never quite broke out of the archetype of the lovable psychopath, even if he had a long career of astonishing work. Pretty Poison does feature some elements that clearly show that Perkins was cast to capitalize on his former role, particularly in how the character is composed to be akin to the sinister sincerity of Norman Bates – the difference is that Perkins deviates from expectations by going another direction with the character, with his blend of calculating malice and genuine torment at having realized that he has once again fallen into a life of crime, are astounding and prove this to be some of Perkins’ most underrated work. Tuesday Weld, an actress who never quite broke out in the way her contemporaries did, is terrific as the innocent, gullible cheerleader who gradually develops into one of the more unique cinematic psychopaths we’ve seen – her final scenes, where she gleefully surrenders herself to a life of complete moral degradation is terrifying, and speaks to this film’s terrific sense of avoiding the predictable.

Pretty Poison is a very simple, but also deeply poignant, character study of a pair of individuals working through their own existential quandaries by engaging in a series of missions that turn out to be thinly-veiled allusions to criminal activity, which takes them from respectful, upstanding citizens, to cold-blooded murderers. We anxiously watch their various misadventures, which Noel Black conveys with such an incredibly poignancy, we often forget that this is a work of fiction. It’s a captivating crime film and a beautifully bewildering satirical comedy that endeavours to venture into the darkest recesses of these characters, exploring their mental state as a way of commenting on the idea of two different breeds of psychopath – one who is acting in this way as its the only way he knows how to survive, and another who finds pleasure in wreaking havoc on this strange, disconcerting world. Pretty Poison is certainly not a film that can be described coherently here, mainly because it makes some bold choices particularly in its tone and how it evokes a certain atmosphere. Whether you view it as a misunderstood cult classic, or a cheap attempt to enliven the exploitation thriller by adding in comedic overtones and a romantic subplot, Pretty Poison is a tremendously effective work, one that thrives on its originality (even if it does seem to be composed of fragments of past and future works) and its pure audacity, especially when it comes to descending to the most primal, instinctual elements of the human condition. It’s buoyant but never slight, which is the precise reason why this is a brilliantly underrated work, and one that deserves another look.