When it comes to comedy, a film can go one of three ways – the first option is that it becomes hopelessly dated as time goes on, especially if it is a very topic subject. The second is that it maintains its level of humour and is viewed as a funny but otherwise inconsequential product of its time. The third, and most intriguing, is when it somehow becomes funnier over time. This doesn’t happen often and is usually reserved for films that were misunderstood on their original release, and very rarely for those that were considered major successes from the start. Tootsie undeniably falls into the latter category, which is an impressive achievement considering it was almost uniformly considered a brilliant and effective comedy when it was released. Forty years later, Tootsie is not only just as funny and insightful as ever, but it has only grown to be more relevant, being the kind of warmhearted satire that never sets out to eviscerate its subjects, but rather playfully lampoon them while provoking a certain level of thought amongst the audience, who have walked away from this film both entertained and inspired for decades, a pattern that is seemingly not likely to slow down as it continues to grow in estimation. Sydney Pollack was one of the most genuinely versatile directors to ever work in Hollywood, someone capable of running the gamut when it comes to emotions and making nearly every one of the films in his lengthy career unique and captivating in their way. Tootsie is one of the true gems in his career, and with a cast as excellent as this, and a script written by some terrific artists in their own right (and polished by a surprising set of script consultants, among them Elaine May and Barry Levinson, both of whom would forge lasting connections with the film’s star), it’s hardly surprising that this film has stood the test of time and become a cherished and iconic comedy that has never felt more charming as it does now, proving that well-made humour never ages to the point of irrelevance.

For about as long as comedy has been made, there has been a universal belief that the image of a man in a dress is shorthand for an easy laugh, a sentiment that has only started to shift in recent years, as a result of gender dynamics changing and a more open-minded approach to storytelling that doesn’t want to aim for the low-hanging fruit, since not only are we more aware as a culture, we also don’t find these kinds of jokes all that funny anymore, unless they’ve developed into being more subversive, in which case they’re somewhat effective. It is also not our place to deem previous works as entirely invalid based on how they portray certain issues – we can question and provoke discussion, but comedy (like any kind of art) develops over time, changing to fit. Tootsie has been one of the rare instances of this kind of story that was not viewed as mean-spirited at the start and has remained quite beloved since then, avoiding controversy and being extremely effective, even despite the movement towards more socially aware approaches to such material. Films like this and Some Like It Hot are terrific comedies that may focus on the “man in a dress” trope, but there is never a single moment where it feels like it is coming from a place of mockery or derision, whether it be to women or men who defy gender conventions. It isn’t entirely flawless, and there are a few off-colour comments that would not work in a contemporary context, but for the most part, Tootsie finds interesting ways to insert humour into the story, creating a scenario where the central conceit of a man who can only get work through dressing as a woman is charming and entertaining, rather than being a series of poorly-timed jokes designed to mock the subject. It’s the sign of not only a well-written script, but also the general desire to never punch downwards, instead choosing to go in pursuit of more bespoke methods of humour, which may not be revolutionary but have a solid basis, rather than just existing for the sake of a quick laugh, which far too many films employ as their primary method of entertaining viewers.

Much of the success around Tootsie can easily be attributed to Hoffman’s performance, which is undeniably one of the best of his career. There is a very interesting detail that we can find in the work he is doing here, whereby despite having done many comedies throughout his career, he is not always considered an actor who is particularly known for humour, and some of his most important work has been in slightly darker projects that draw on his dramatic skills. Yet, he is still extraordinarily funny when he needs to be, and he is the perfect person for the part of Michael Dorsey, a washed-up actor who decides to surrender to the urge to adopt a new identity as a last resort to gain employment. What is most intriguing about Hoffman’s performance is his approach to the material – he has a reputation for being relatively dour and has always taken himself extraordinarily seriously, which has benefitted him in the form of allowing him to commit fully to every role, but which has also given him the reputation of being somewhat difficult to work with – and few people could have done this role better than him, since the entire plot focuses on an actor who is very gifted, but whose own tendencies towards pomposity and the refusal to take criticism is reflected in a lot of the choices Hoffman made as an actor. He maintains that he never viewed Tootsie as a comedy, and this is the key element that elevates this film – this is a very funny story, but Hoffman plays the part with total earnestness, never once mugging for the camera or making it obvious that he was trying to go for the laughter, leaving it up to Pollack and his co-stars (which include tremendous performances from Teri Garr, Bill Murray and Jessica Lange, amongst others) to bring forward the hilarity – and it may sound like a strange approach, but its one that works in this specific film, since its one of those rare comedies where the plot is even funnier when it features someone who plays it completely straight, as if they were in a sobering drama, since it only emphasizes the central themes in a way that feels authentic – probably because there was some degree of honesty in how the film uses Hoffman and his reputation, allowing him a safe space to riff on how he was perceived, while still delivering an excellent and bitingly funny narrative alongside it.

Perhaps the reason Tootsie has continued to resonate with viewers all these decades later is quite simply the fact that it knows how to balance its comedy in a way that is effective and insightful. This is primarily a satire on the media, and considering how the concept of celebrity culture and the idea of fame has never been more relevant today, it’s easy to understand why it has continued to be appreciated as a work of very effective comedy. It may lack some of the nuances we’d expect from a modern retelling of this story (since much like comedy, the media landscape has changed over time), but it still has a solid foundation within exploring celebrity culture, and how easy it is for someone to take advantage of gullible audiences, who don’t pay enough attention to their entertainers, allowing them to get away with some truly bizarre antics that either go entirely unnoticed, or (as a result of more modern approaches to fame) become tabloid fodder. Andy Warhol himself has a very brief appearance in one of the centrepiece scenes, which hammers in the theme of everyone having their fifteen minutes of fame, which is essentially the entire concept on which this film is constructed. Pollack does well to avoid becoming too heavy-handed, allowing the film to rapidly approach some very serious conversations, but swiftly positioning it back within the realm of broad comedy before it becomes too dark – we’ve seen enough examples of celebrity culture being filtered through a very bleak lens, so there is value in one that allows a more upbeat version, one that almost borders on sentimental, but in a way that is active and endearing, rather than just being there for the sake of challenging conventions that were not that complex in the first place. Tootsie is a carefully constructed work of cultural satire, one that works a lot better when it is actively trying to find humour in places that we wouldn’t expect, and it’s the aspect that allows it to be such a cherished comedy, even after so many years have passed.

There have been countless imitations of Tootsie over the years, both in terms of works that actively acknowledge it as a source of inspiration (such as a mildly successful stage musical, which is far more popular with audiences than critics), and those that just blatantly copy it, citing the belief that this was just parroting Some Like It Hot, when nothing could be further from the truth. This is a vibrant, bitingly funny satire that combines many different ideas, each one developed in a way that is earnest and never feels anything less than totally authentic, both in conception and execution. Few actors are better suited for this material than Hoffman, who gives one of his very best performances, challenging conventions in a way only the most talented actors could – and as a result, he helps create one of his most memorable performances in a film that served as a springboard for others, like Garr and Lange, to do some of their best work as well, especially the latter, who may not have been the most prominent part of the film, but who seemed to earn a lot of goodwill based on her performance as the delicate but feisty love interest. As both a satire of the entertainment industry and a comedy about gender dynamics, Tootsie is a marvel, a film that becomes only more captivating with every subsequent viewing, since there’s an abundance of detail that we often miss on the first journey through the story, and which only further visits can help reveal. There are very few surprises in this film, and you can easily predict where it is heading after a while – but this makes it neither unoriginal nor unnecessary since the experience of seeing this entertaining story transpire with wit and candour is worth the price of admission in itself. Forty years on, Tootsie is as funny, relevant and entertaining as ever, and even with a couple of dated jokes and a few references that keep it contained to a particular era, it is fresh and charming and continues to be a source of continual inspiration for those wanting to experience a true masterclass in well-crafted comedy, which is the exact description that this film has worn with pride over all these years.