I love stories that take place over a single period of time, whether an individual night or a slightly longer stretch, where everything is contained into something slightly more manageable. I once recall driving through a city at night with a friend, and remarking to him how I am still waiting to have my own “one crazy night” adventure, since cinema has always made it seem like an irresistible and inevitable scenario where everyone has the opportunity to experience the madness of reality condensed into a single evening, or in some cases a few connected evenings that come together to form a more coherent whole. There are a few canonical works of cinema that explore this idea, and we often find that they tend to be wickedly entertaining, even when they can sometimes be quite far-fetched and unrealistic at the best of times. One of the more intriguing theatrical works of the 20th century (albeit one that has always received a slightly mixed reception) is The Owl and the Pussycat, written by Bill Manhoff and originally staged in the 1960s, in which a pernickety writer has his world turned upside down with the arrival of an eccentric model, who takes up residence in his apartment after being evicted from hers. Over the course of a single night, the pair engage in a passionate battle of the wits, a ferociously entertaining tug-of-war in which every topic they can imagine – from the meaning of life to the colour of lingerie – is discussed in detail. It’s a fascinating work, and one that unsurprisingly became quite a counterculture sensation, even if it has not quite maintained its reputation to the present day. The inevitable film adaptation was directed by Herbert Ross, the journeyman filmmaker who was often hired to bring these theatrical works to life on screen, which he did in collaboration with Buck Henry, who is tasked with writing the screenplay that slightly expands on the play while also maintaining its rebellious message. The result is unfortunately a bit of a mixed bag, a film that is undeniably entertaining but which lacks something precise beneath the surface, which is a product of a few small shortcomings that coalesce into something that squanders its immense potential.

Context is always vital when venturing into these provocative satires from previous decades, since while they should ideally age in such a way that modern viewers don’t need an abundance of knowledge to understand what they are saying, there should be some degree of insight into the dominant mentalities at the time for us to pick up on the nuances, especially when dealing with something that makes some very intriguing statements on the culture from this period. The premise of The Owl and the Pussycat immediately leaps out at us without any prior context, since it revolves around a writer who fashions himself as a very serious intellectual, and a woman who simply wants to live life on her own terms, regardless of what those around her say to be acceptable. One is driven by the strict rules of the status quo; the other cannot fathom following any conventions if it means she is stripped of her individuality – but despite their stark differences, they find common ground. If this is not the very definition of the counterculture movement that reached its apex in the 1960s and would continue on for several more years as the world continued to witness monumental change, then nothing else is. A very simple premise that pits two wildy different personalities against one another, forcing them to engage in a hilarious and often insightful tug-of-war that is more than just your conventional battle of the sexes comedy (although this is the foundation for the narrative as a whole), The Owl and the Pussycat does have a lot of promise, made even more enticing by the presence of the always reliable Ross, as well as the unsurprisingly crackling dialogue of Buck Henry, who may not have quite the same spark as Neil Simon (who usually peddled in this particular brand of eccentric urbane comedy), and it touches on some very progressive themes that were radically ahead of its time, such as the destigmatising of sex work, body positivity and unconventional relationships, proving to be quite a captivating work, even at its most traditional and straightforward.

Unfortunately, there are a few areas in which The Owl and the Pussycat does falter, and one of the most prominent comes as a footnote to the sentiment of this being a film that was ahead of its time. The original play is ambiguous enough about its characters and their origins that any performer would have been able to play the part, something that productions often acknowledged by taking the opportunity to cast the film with leads from different races, and therefore including a notable statement on interracial relationships, which was still a topic of contention at the time. The film was designed as a vehicle for Barbra Streisand, who ostensibly intended to court Sidney Poitier to play the male lead. The very prospect of these two titans being paired together in this witty, complex comedy seems almost too perfect, and unfortunately it was deemed unfeasible, a product of a film industry that wasn’t quite ready to embrace such a progressive premise, at the risk of stirring controversy. Needless to say, they did the best that they could with the pairing we were given, which saw Streisand acting across from George Segal, who was by no means a poor actor, but who lacked the specific whimsy and eccentricity that an actor like Poitier would have brought to the role. Nevertheless, there is still value to be found in this film – Streisand is as charismatic as ever, and while some may accurately describe her performance as Doris to be a dress rehearsal for the chaotic perfection she’d achieve a couple of years later in What’s Up Doc?, the reality is that she’s such a magnetic personality that she’d be able to shine in just about any role, and that is certainly the case here. Segal is also quite good, since he draws on his gifts as a character actor to develop Felix as a delightful curmudgeon, and while Streisand does run circles around him (which should be obvious to anyone aware of her immense talents), he does hold his own. They don’t have quite as strong a chemistry as we would hope, but they’re still doing strong work, enough to compensate for some of the more dire shortcomings that emerge throughout the film.

Unfortunately, the flaws present in The Owl and the Pussycat do tend to derail it from time to time. The problem isn’t that there is one or two enormous shortcomings, but rather several small issues that all come together to create a work that is slightly misaligned and lacking in coherency, which is not ideal for a story that is earnestly trying to represent several deeper themes. The challenge here wasn’t that the actors don’t have chemistry (they may not be instantly compatible and may sometimes struggle to connect in the same way that they would with other on-screen partners, but they get along decently well), but rather that the film doesn’t quite know how to navigate the relationship. The nature of live theatre means that a lot of the experience comes in the energy present in the moment, which is sadly lost on screen in many cases, and we find that to be the case here – its a film that relies heavily on the dialogue, and while it is not the first instance of a romantic comedy that veers towards the verbose, Ross struggles to find the right tone, and as a result we find that the film is stuck in limbo between outrageous humour and more melancholic, sensitive complexity, which is not a place where any film wants to settle, since we can’t ever be sure what it intends to communicate. The bittersweet tone does work to an extent, but when the conclusion feels so rushed (not to mention entirely obvious), it can undo some of the promise made before that moment, since we’ve been led to a particular point and not given the conclusion that we were hoping to receive. It also occasionally struggles to establish a clear message, since one of the pivotal aspects (albeit one that is intentionally left unspoken in the play, relying on subtle cues in the casting to reflect the dynamic between two characters of different racial backgrounds) was entirely removed, taking away one of the more intriguing elements of the story and reducing it to just another offbeat romantic comedy about ordinary people bickering through the process of falling madly in love with one another.

While it may be harsh to call it a failure (it’s not an atrocious film by any means, but its inability to strike the right tone does mean that it falters more often than it succeeds), we do find that The Owl and the Pussycat is a bundle of missed opportunities, a film that has broad ambitions but limited scope, and which ultimately doesn’t succeed as much as we may have hoped at the outset. It doesn’t completely waste our time, but it lacks a certain spark that not even the eternally charismatic Streisand or effortlessly likable Segal can entirely overcome, a result of a film that tries too hard to go in one direction, but misses every opportunity to go in another one, which may have meant that it lost some of its consistency, but in favour of something far more interesting. It’s not nearly as dynamic a film as we would expect, and its commentary, while radical in some ways, does feel ultimately quite dated, since it approaches these topics without always being able to flesh them out in their entirety. Part of this is due to the conventions at the time, and it is very likely that had this film been given more freedom, it would’ve been far more revolutionary. However, we can’t blame the frequent tonal irregularities and slightly unenergetic filmmaking on this, since that is purely the result of Ross’ direction, which is not bad so much as it is very traditional, not realising the opportunity to experiment with form and style in a way that would at the very least be considered enticing. It’s not a failure, but in many ways I do wish it had been one, since it would’ve likely been a noble misfire, rather than being merely a mediocre bundle of obvious ideas masquerading as something far deeper than it could have ever been with such a conventional set of intentions driving this story forward.