The first scene of The Heartbreak Kid starts where most movies end – with a wedding. We’re introduced to Lenny Cantrow (Charles Grodin), a young man who is about to be wed to his sweetheart, the loud but kind-hearted Lila (Jeannie Berlin). The pair head to Florida for their honeymoon, hoping for some quality time to spend their newly-married life together. However, Lila proves to be a lot more incompatible with Lenny than he originally thought – she means well, but her quirks slowly start to erode his patience, and he finds himself falling out of love with her after only a few days of being married. It also doesn’t help that he meets Kelly (Cybill Shepherd), a rich Midwestern woman who instantly beguiles Lenny, who can’t help from falling in love with her, despite being on his honeymoon. Lenny, caught in a difficult situation where he is forced to choose between honouring the sanctity of marriage and the woman he chose to spend the rest of his life with or following his heart, even if it means breaking that of another in order to satiate his own desires. Our protagonist has his work cut out for him, and his decisions, as important as they may be, are certainly not very easy to make.
Elaine May’s The Heartbreak Kid is quite a film – taking its cue from the rising popularity of alternative forms of cinematic romance, its a daring and very idiosyncratic comedy that not only allows May the chance to continue to explore her roots as director, but also serves to be an addition to a canon of romantic comedies that is a lot darker, more serious and darkly comic in its approach to some difficult subjects. Perhaps not the steadfast masterpiece that her directorial debut, A New Leaf, was, May’s sophomore effort here is certainly still an impressive achievement, an arid but irreverent portrayal of modern romance, a subversion of the saccharine, innocuous portrayals of love that were perpetuated by a long tradition of fiction following the same constraints in how it showed love as being far more complex than it is. Bold and not without its broad charms (and perhaps even some flaws that actually turn out to be merits when taken in the context of the film as a whole), The Heartbreak Kid is a fascinating character study that shows that love, like everything else in life, is not particularly easy to understand, nor all that simple to define.
Love is a many splendored thing, as the old adage goes. What very few portrayals of romance ever show is how endlessly confusing it can be as well – and this serves as the impetus for The Heartbreak Kid, which endeavours to show a different form of romance, one that is closer to reality. May had previously explored the subject in her previous film, and is diving deeper into the subject here through the character of Lenny, who is a man who doesn’t seem to know what h wants, although he is more than happy to go to any lengths to achieve it. May’s vision of romance takes a very different form here, and the film is characterized by being perhaps the most uncomfortable romantic comedy ever made – whereas other films with this kind of subject matter would tend to find cohesion in order to sew up the gaps in the fabric of the narrative, The Heartbreak Kid openly embraces these loose threads, and crafts something so endlessly uncomfortable, it barely even registers as a romantic comedy, as it goes against everything that normally defines the genre. It’s even possible to consider this film a comedy, and that it’s about romance, but it would be a stretch to consider them together.
This may seem like a criticism, but it is one of the ways The Heartbreak Kid establishes itself as a very unique film. Despite the fact that it occurred around the time when romantic comedies were heading for their peak, it is remarkably different from them in a lot of ways. The spectre of The Graduate looms heavily over the film here, but in a way that allows The Heartbreak Kid to complement it rather than be seen as being an attempt to capture the same misanthropic delights set out by May’s comedic partner Mike Nichols in that generation-defining film. What the director does here that impressed me the most is her ability to keep everything so authentic. Everything about the film indicates that it is anchored very much in reality – the characters may be despicable, but they are genuine, and May utilizes a lot of her keen observational comedy skills to derive every bit of truth out of the situations she depicts. It is honest, straightforward and certainly disconcerting, solely because the film taps into a certain element of romance that is hardly ever shown in romantic comedies – whereas most films in the genre would end with the fairytale wedding, The Heartbreak Kid begins with one, and shows how modern romance is starkly different from how its perceived in fiction, and that while it is possible to earnestly fall in love, its not always as easy to stay in love as it would appear.
The Heartbreak Kid is really defined by its tendency to be solely about terrible people. The protagonist is the antithesis of every kind of romantic comedy lead we have grown accustomed to – Lenny is sardonic, rude and an opportunist who makes impulsive decisions in a way that only serves his own desires, and is willing to do absolutely anything to get what he wants, often not even realizing precisely what that is. Deception forms the core of the film, and the majority of the characters seem to be operating on some level of hiding their true colours in some way. Lenny, in particular, is a fascinating individual, mainly because everything about him should be absolutely despicable, and there isn’t a redeemable quality to be found anywhere within him – yet May constructs him as someone who we acknowledge as being a terrible person, but we can’t help but become invested in his journey. In a way, while he may have his enormous faults and may lack the moral grounding these characters tend to exhibit as ideal romantic representations, Lenny is an honest representation of a certain kind of person who is submissive to two emotional qualities: indecisiveness and selfishness – Lenny doesn’t know what he wants, but he surely knows he wants it badly, and all to himself. His third quality is the one that actually seems to be his most positive trait: he is tenacious, and his impulsive behaviour indicates that below the self-serving arrogance sits a very hard-working young man willing to do anything to achieve a certain goal, even if it is one that prevents another from achieving theirs.
In creating the characters, May makes use of a talented ensemble that interprets the story very well. Like many works written by screenwriter Neil Simon, The Heartbreak Kid is a magnetic force for gifted performers, many of them understanding the enormous opportunity that comes with working with the legendary writer. Charles Grodin leads the cast, and he gives a terrific performance as a young man doing anything to get what he wants. Far from the archetypal leading man, Grodin manages to command the screen, even when he doesn’t intend to – whether in moments that require his distinctive cold, standoffish detachment, or those when he is operating on the manic level, jabbering away with a fierce intensity, he’s tremendous, and finds a truthfulness in a character that was essentially a villain written as the protagonist of a romantic comedy. Its a tall order, but he carries the film almost entirely on his own. Another highlight of the film comes in the form of Jeannie Berlin, who quietly gives the film’s best performance, as the blissfully ignorant Lila, who is hopelessly in love with a man who secretly cannot stand her. The film is not very fair to Lila as a character, and she disappears at the end of the second act, which is perhaps my only qualm with the film, but one that could be justified as simply being a result of the film’s ruthless approach to the conventions of the genre. There was another film lurking in The Heartbreak Kid, one told from Lila’s perspective, that would’ve been equally as compelling. Finally, Cybill Shepherd is given a character that at first just appears to be built on her physical appearance – a woman who attracts Lenny based solely on her appearance. However, the film does afford her the opportunity to actually be built in an honest character on her own, and Shepherd is able to demonstrate a comedic sensibility that wouldn’t be utilized to its full extent until decades later. The Heartbreak Kid is a small and intimate comedy, and one driven almost entirely by the characters, so it only makes sense that May would make sure the performances she derived from her cast were enough to keep up with the sometimes intimidating dialogue provided by Simon, who knew how to craft character-driven comedy like very few others could.
Of everything that we can praise this film for, perhaps what is most impressive is how The Heartbreak Kid managed to be one of the very first truly successful comedies that rely on questionable behaviour to portray reality, and while it isn’t something employed very often – not many of us are entirely interested in films that focus on terrible people getting away with their poor moral judgements – although some will argue that the ending to this film is extremely bleak, as we watch Lenny once again grow disillusioned with his choice, on yet another wedding day – it still makes for captivating viewing here, with May creating something very special and undeniably unique in its approach to a very common subject. This kind of neo-realist romantic comedy was certainly ahead of its time and would find its home more in the realm of independent cinema, where this brand of nihilistic, acidic romance could flourish without the constraints put upon the genre in the mainstream. The Heartbreak Kid is clearly a film that is taking advantage of its liberation from the confines of the industry, and it proudly embraces its status as a nasty, uncompromisingly bleak and uncomfortable representation of a different kind of romance, one not built out of lovable personalities and life-changing coincidences, but from unlikable individuals and uncomfortable situations.
While it may be darker than other films in the genre, it’s also funnier and more fascinating, because when confronted with the chance to make an innocuous romantic comedy, or to subvert expectations and deliver something truly original, its clear which one Elaine May would choose, and we’re all the better through her decision to take on the most sacred of institutions with her sarcasm and intelligence, which translate into one of the most gorgeously unsettling comedies of the 1970s. Funny, insightful and thought-provoking, the film benefits from a set of terrific performances, a brilliant premise and rapid dialogue that all converge into a unique and daring character-study that takes an unconventional approach to one of the most beloved genres, resulting in a film that may not be particularly pleasant at times, but remains hilarious and outrageously brilliant from beginning to end. It takes many risks, and while it may not always pay off in the way one would hope it would (there are some moments in The Heartbreak Kid that really don’t work), the final result is a film with a devil-may-care attitude towards a genre defined by its oversentimentality, broad archetypes and predictable storylines, which May and Simon take enormous contempt with, delivering a truly unromantic comedy that has more to say about love and the nature of desire than nearly any other film produced during this period did, which is an impressive achievement, and proves that despite being a slow-burning, measured narrative experiment, The Heartbreak Kid really is just as brilliant as one would expect from the beautifully deranged comic mind of Elaine May.
The Postmodern Pelican 
Neil Simon is known for adaptations of his Broadway comedies that are equivalent to hit TV situation comedies. The movies get the laughs they seek and are forgotten by the time the audience arrives home. Simon wrote the screenplay for the 1972 comedy The Heartbreak Kid. The screenplay was adapted from a short story by a writer Simon long admired, Bruce Jay Friedman. The cringe-inducing comedy and character-based laughs were a sidestep from Simon’s typical situation comedies.
Simon wrote the screenplay during his beloved first wife’s battle with cancer. That may well have contributed to his creation of the unexpectedly dark comedy. As was typical with his screenplays, his contract contained a specific clause that every word must be spoken as written without variation. Simon was needed during his wife’s last days. Director Elaine May convinced Simon to give her authorization to make changes. May had developed her talent in a famed comedy team with Oscar winning director Mike Nichols. She thrived on improvisation and used it extensively while filming The Heartbreak Kid.
The story follows Leonard Cantrow, a three year Army veteran, who will soon marry Lila Kolodny, a 21 year old virgin. Despite Leonard’s best efforts, Lila denies Leonard sex till their wedding night. The event is disappointing. Leonard finds his bride’s need for assurance annoying and doesn’t want to talk after lovemaking. Their honeymoon is a road trip to the beach in Florida. At one stop, Lila eats a messy egg salad sandwich with great enjoyment. The resulting and untended smear of egg salad across her face repulses Leonard.
For audience members who have endured long confinement at the start of a new relationship, the experience is telling. Ticks and idiosyncrasies become apparent and test the bonds of affection. Lila loses. After she refuses Leonard’s offer for sun screen on their first beach day, she is horribly burnt. While Lila is recuperating in their hotel room, Leonard and a young and affluent college coed Kelly Corcoran engage in serious flirtation. Leonard must have this blonde beauty and impulsively decides to end his marriage to woo and win her.
Charles Grodin was 37 when cast in this role of a man in his early 20s. He lost most of his excess body weight to gain the lean look of a young man and wore a hairpiece to mask his age. It is effective. Leonard frequently reminds characters of his three years of Army service and how it aged him.
Leonard Cantrow is a horrible human being. His immediate distain for his new bride alienates him from the audience. His desire to throw away his three day old marriage for a stunning WASP girl makes him more despicable. Director Elaine May films the scene where Leonard dumps Lila in a Florida seafood restaurant. Like the beach resort where the newlyweds are staying, the eatery is a favorite for vacationing Jews. As Lila understands Leonard’s mealy mouth wish for an annulment, May continually cuts to the older Jewish women at neighboring tables listening to Leonard’s fumbling excuses and Lila’s hurt. At first funny, the faces embolden our anger at the public humiliation Lila is enduring. And yet we are still laughing. Grodin is masterful at making us dislike Leonard and still root for him to get the other girl.
Simon had advocated for then noted Broadway comedy actress Diane Keaton to play Lila. May disagreed. She felt the comedy required an actress who was not so attractive. She cast unknown Jeannie Berlin. Berlin was simultaneously hilarious and heartbreaking. She appeared to have no vanity and willingly did extreme close ups with remnants of egg salad or gobs of sunburn cream on her face.
Her brilliant performance won Oscar and Golden Globe nominations as well as the New York Film Critics Circle Prize for Best Supporting Actress. It wasn’t till filming began that it was revealed that Berlin was May’s daughter. Despite her rave reviews, Berlin subsequently worked very little, twice taking more than a decade off between film projects. Most recently, she has won acclaim as the prosecutor in the HBO miniseries The Night Of.
Two other surprising performances came from this caustic, dark comedy. Cybill Sheppard, a model who won the attention of director Peter Bogdanovich in manner similar to Leonard’s attraction to Kelly, was very good in the film. In interviews, Sheppard commented that May worked with her on her acting and taught her that listening was important. You can see the effect of May’s tutelage. There is meeting between Kelly’s father and Leonard. Sheppard is seated between the two observing. As brutally funny as the scene is, the eye constantly returns to Kelly. The camera keeps both men on either side of the frame. Silent Kelly remains the focus of our eye. We aren’t sure if the woman who prompted this man to end his marriage on his honeymoon is the love of her life, an effort to anger her authoritative father, or simply a vacation amusement. All seem possible, and it may be that Kelly is too young to know either. Yet, during the intense discussion her eyes dart from her father to Leonard like watching a tennis match. She smiles slyly in certain moments that only further confuse the viewer on her intent. Throughout the film, May focuses on silent women who observe the actions of men. This frequent technique becomes the director’s commentary and our moral compass.
Best Supporting Actor nominee Eddie Albert is wonderful here as Mr. Corcoran. He is a bigot. While the film features a detailed Jewish wedding for Leonard and Lila, May never pushes the obvious hatred Corcoran feels for Leonard Cantrow upon sight. Kelly tells Leonard that her father is moving to a new resort because of the “element” found at this resort. The camera then cuts to the many Jews around the pool deck. The anti-Semitism is clearly evident. Mr. Corcoran is rigid in his stress level. At a nightclub performance Leonard moves a chair next to Mr. Corcoran. Albert, who was long typecast as the affable second banana, visibly conveys the surging rage underneath the surface of this overly protective father. You are never quite sure if his threats are not actually real and Leonard may provoke him to violence. And yet, Albert underplays the moments with a wit that rings laughter out of each encounter.
The film is great. May pays tribute to her former comedy partner Nichols and his Oscar winning The Graduate in the final scene. The camera focuses on Albert tensely observing Leonard chatting with some children. It is a surprisingly caustic comment on this man and how he impacts those around him.