To make a comedy film is to reckon with the odd bedfellows that lie at the heart of the genre: danger and comfort. The two concepts are antithetical but are absolutely essential if a film is going to make us laugh. A comedy without any sense of risk will never get its audience invested enough in the proceedings to be truly funny. It’ll have no stakes, no bite, no reason to care. But it’s not enough to make a situation dangerous – played straight, a man tripping and falling is not funny. It can, however, be made humorous if the filmmaker creates a sense of comfort around whatever is happening, if they remind us that we’re only watching a film. That’s where the familiarity of the banana peel, the exaggerated movements, and the elaborate physical choreography comes in: they create distance between the audience and what we’re watching, a sense of comfort. “Yes,” the comedy film will whisper in your ear, “that is a dangerous tumble that fellow just took, but don’t worry, it’s just a movie. He’s in danger, but you’re safe. Yes, it’s all right, go ahead: laugh.”

Danger and comfort. This is the challenge that every great comedy filmmaker has had to tackle. Charlie Chaplin roller-skated, blindfolded, towards the ledge of a balcony.  Howard Hawks put Cary Grant in the same room as a live leopard. Ernst Lubitsch had a Polish acting troupe infiltrating the Gestapo. Stanley Kubrick brought the Cold War to a boil. Mel Brooks opened Springtime for Hitler on Broadway. Trey Parker and Matt Stone put Satan in bed with Saddam Hussein. How do you make these shocking, distasteful, perilous, vulgar, or treacherous situations palatable without rendering them inert? That’s the challenge, that’s the tightrope.

Enter Billy Wilder, professional cinematic tightrope-walker

In all the annals of film history, few have struck this balance as adroitly or as confidently as Billy Wilder. A German émigré who started his Hollywood career as a screenwriter, Wilder soon transitioned his career into being a God of Cinema. Even if he hadn’t done genre-defining work in the fields of film noirs, courtroom dramas, and war films, Wilder would have a seat reserved in the filmmaking pantheon for all eternity just for his work in comedy. Never a man to shy away from provocative subject matters, Wilder mined for jokes in topics as somber and controversial as organized crime, war, infidelity, prostitution, East-West tensions, Communism, Nazism, murder, violence, and suicide. And moviegoers everywhere laughed and laughed and laughed. Every time Wilder pushed the envelope further, and every time he hit the bull’s eye.

Then he made Kiss Me, Stupid.

Push the envelope enough times, and the envelope pushes back.

Kiss Me, Stupid, released in 1964, was the third film that Wilder directed after his controversial monster hit and triple Oscar win for The Apartment. It’s a film that was made at the height of his powers, but it’s also one that suffered from considerable setbacks. Wilder originally wanted Jack Lemmon for the lead role in the film, but when previous obligations made his usual partner in crime unavailable, Wilder settled on Peter Sellers. Yes, that Peter Sellers. The idea of a Sellers/Wilder film is enough to provoke acute salivation in most film lovers, but God decided that the result might be a bit more than the world could handle. Sellers had to be hospitalized after a heart attack shortly after filming started, and Wilder was forced to recast and reshoot. After that hurdle, he had to deal with an even bigger problem: the Catholic Legion of Decency. The fine folks at the C.L.D. objected to Wilder’s finished film and, dissatisfied by cuts he made to appease them, condemned the film publicly. This led to distribution problems, which were only exacerbated when the reviews for the film came in. The film was widely panned by critics and the masses, the general consensus being was that it was unfunny vulgarity that lacked the nimble wit and sophisticated charm of the previous Wilder films. Few saw it, and the ones that did left the theater with a bad taste in their mouth.

What went wrong? Had Wilder’s taste for the provocative finally gone too far? Had his reach into the realms of the dangerous and the shocking finally exceed the grasp of the comfort he could bring to the proceedings? Well… maybe.

Dean Martin drinks Chianti out of Kim Novak’s shoe. I think that kind of covers everything you need to know about this movie.

Orville Spooner (Ray Walston heroically stepping into Peter Sellers’s shoes) is an underachieving music teacher in the sleepy town of Climax, Nevada. He’s married to the prettiest girl in town, Zelda (Felicia Farr), and consumed by paranoid delusions that she’s cheating on him with practically every man in town. He spends his free time writing songs with his friend Barney (Cliff Osmond) but after years of thanks-but-no-thanks and doors slamming in their faces, is starting to fear they’re never going to sell a song. His life’s a neurotic mess, and he needs something to shake things up.

As luck would have it, a famous singer, actor, and philanderer named Dino (played by Dean Martin… more on that in a moment) has pulled into town just in time for his car to break down. By hook and by crook, Orville and Barney are able to convince Dino to stay at Orville’s for an evening, hoping that they’ll be able to sell him one of their songs once he’s a captive audience. Things take a turn for the worse, however, when Orville realizes that Dino is a sex-addicted fiend who’s only interested in seducing women. Rather than let the Hollywood Casanova set his sights on his wife, the two pals come up with a plan worthy of the most convoluted of P.G. Wodehouse novels: they’ll get Zelda to leave for the evening and then replace her with a notorious call girl from the local den of iniquity, a girl by the name of Polly the Pistol (Kim Novak). Polly will pretend to be Orville’s wife, Dino will have his way with her instead of Zelda, somewhere along the way they’ll sell him one of their songs, Zelda won’t find out that any of this ever happened. What could possibly go wrong?

Yup. Solid plan. Totally fool proof.

Just by reading the above description, you might already be cringing a little. Or a lot. It’s not difficult to see why the guys and gals at the Catholic Legion of Decency ended up in a tizzy over this one. Kiss Me, Stupid approaches its subject matters in a way that walks a fine line between “risqué” and “just plain uncomfortable.” The Apartment had dealt with adultery and prostitution, but it used a defter touch, came at these matters sideways. At the very least it did us the common courtesy of having a protagonist that was unambiguously against these matters. Kiss Me, Stupid is blunter, less inclined to comforting niceties. This film feels sleazy by design, and its dangers are more present and alarming, partly because they’re coming out of our protagonists themselves.

Speaking of the film’s protagonists, you may have already surmised this, but all of the men in this film are awful human beings. Barney is perhaps the least offensive of the three, but even he spends most of the film trying to toss girls into Dino’s arms just so he can make a buck. Orville is a jealous, possessive mess. In an early scene he is so obsessed about catching his wife in an imagined act of infidelity that he forgets it’s their wedding anniversary. But both of these sterling examples of horribleness pale when compared to Dino. The film plays the superstar as a one-dimensional, unsympathetic nightmare, a man who is so used to having women throw themselves at his feet that his brain has evolved backwards and erased all notions of consent from his conciousness. In many ways the plot of this film might could be summed up as “two horrible men try to entertain a sexual predator so they can profit.” Gee, aren’t you just itching to spend two hours with these guys?

‘Kiss Me, Stupid’: making you uncomfortable about what you’re seeing since 1964.

Okay, so the people in it are horrible, the subject matter’s uncomfortable, and most people who saw this film wrote it off as vulgar claptrap – why in God’s name am I telling you to watch this thing? Well, for starters, this is still a Billy Wilder joint, so all of the above is presented through some of the most creative, inventive, and sparkling dialogue that you have ever heard. Wilder came up during the restrictive era of the Hays Code and became an expert at getting his audience to deduce what he couldn’t show them. He once famously said that working under those conditions taught him that you should never call someone “a son of a bitch” if you can instead tell them, “If you had a mother, she’d bark.” There is a power in getting your audience to put two and two together on their own, in getting them to supply the dirty joke for themselves. This attitude is in full swing in Kiss Me, Stupid, and the way in which Wilder is able to get us to understand the horrible things that are happening through suggestions, innuendo, and vague allusions is a masterclass in audience control. The film’s content is tamer than most of the things that you’ll see in a modern gross-out comedy or on HBO but still feels outrageously seedy and lewd. Maybe that’s because, rather than just giving us all of the awful things that are happening outright, the film lets us infer and discover a lot of what’s happening. Nobody in the film directly states that Polly is a prostitute – we just know and that makes it all the dirtier.

Billy Wilder and Kim Novak try to come to a decision about a nuanced artistic issue while Dean Martin provides… moral support. The presence of Kim Novak’s “assets” throughout the film was one of the major reasons for the Catholic Legion of Decency’s condemnation of ‘Kiss Me, Stupid.’

Secondly, the film’s performances are reason enough to check out this black diamond in the rough. Ray Walston is a bit out of his depth in a role that was clearly designed for a comedy titan, but he gives it his all and acquits himself admirably. Kim Novak, on the other hand, brings layers upon layers to one of the best performances of her career. Polly is supposed to be a straightforward participant in the schemes, but she actually emerges as the film’s most complicated and three-dimensional character. Novak handles each of her transformations and turns with pitch-perfect vulnerability and likability. The powerhouse, however, is Dean Martin. The Rat Packer had already been playing thinly veiled versions of himself in his films with Jerry Lewis for years, but this was something different: a biting, mean-spirited satire of the darker side of his public playboy persona. It’s the kind of performance that a lesser actor might shy away from, but Martin commits to it wholeheartedly and makes Dino an animal.  It’s a brave, take-no-prisoners performance, both a precursor and a towering superior to the self-parodying antics of films like This is the End.

In spite of the film’s critical and commercial failure, Wilder spoke highly of the experience of working with Dean Martin for the rest of his life.

And, finally, the film is really, really funny. Oh, it’s uncomfortable and challenging, and definitely not for everyone’s taste, but if you are a fan of black comedies, this is a beast unlike anything you’ve ever seen. The filmmakers definitely went all out with how much awfulness and reprehensibility they could stuff into one film, but they also remembered to add the comfort necessary to make the proceedings funny. Everything in the film is stylized and exaggerated, from the hyper-small town setting and all the male characters’ one-dimensionality to Dino’s over-the-top portrayal. The entire thing feels like a deranged, breakneck-speed cartoon, but one that revolves around seedy and shocking subjects. Put all of this together with Wilder’s unparalleled ability to assemble funny set pieces, his ever-inventive reversals of roles, and his flawless comedic timing and what you get is the most uncomfortable set of laughing fits any film will ever give you.

There’s a scene early in the film where Orville is trying to get his wife upset enough to leave their home before she runs into the philandering Dino, an enterprise that proves a lot more challenging than one might think. He starts by saying very upsetting things to her, and these only escalate as she shrugs them off and he gets more and more desperate. The problem is that it’s such an unrelenting onslaught of awfulness, and Wilder couches each of the heartless things he says in such creative articulations, unexpected turns, or deadpan deliveries that my brain just ends up laughing because it has no idea how else to process what’s going on. No matter how many times I watch this scene I always feel like a worse human being by the end of it. Kiss Me, Stupid turns fifty years old this year and it feels shocking and unsettling now, almost like after all these years we’ve caught up with it and it can finally push the envelope the way it was meant to. Every time I watch this film I gasp and my jaw drops and I feel like a horrible person… and then I laugh and laugh and laugh.

Sure, it’s kinda dirty and raunchy, but you know what they say – nobody’s perfect.