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Directing a romantic comedy this well is an Oscar-worthy achievement

Oscar ThisThe Academy Award nominations are announced every January. With Oscar This, The A.V. Club stumps for unlikely candidates—the dark horses we’d love to see compete on Oscar night.

Only four women have ever been nominated for a Best Director Academy Award. The reasons for this can be broken down into dozens of variations on institutional sexism, all tangled together with each other and with Hollywood’s various other predilections, prejudices, and unofficial rules. One of the most practical reasons has to do with the same reason that far fewer women are given shots at directing preordained blockbusters like Jurassic World: Hollywood as an institution has very clear and foolish ideas about genres and skill sets. Not only are a lot of female directors consigned to directing romantic comedies or family dramas, the current voting body doesn’t seem to care or even notice when a romantic comedy is well-directed. (Imagine a movie like Annie Hall or The Philadelphia Story getting made today and managing to garner awards attention for the effort).

This genre bias in business and prestige is helped along by sexism, too, of course; the only feature Colin Treverrow made before he was signed on for Jurassic Park and Star Wars movies, Safety Not Guaranteed, is essentially a romantic comedy, as is David O. Russell’s awards-friendly Silver Linings Playbook. But for whatever silly technicalities—the merest smattering of science fiction in Safety; the seriousness of the mental illnesses chronicled in Silver Linings—those movies aren’t thought of as “just” rom-coms. A romantic comedy that’s upfront about its genre, meanwhile, gets stuck in a system that doesn’t differentiate between an indifferently or outright incompetently directed one, like Anne Fletcher’s The Proposal or almost anything from Garry Marshall, and a beautifully directed one, like Leslye Headland’s Sleeping With Other People.


Headland has directed only two feature films: the wonderful Bachelorette, based on her stage play; and Sleeping With Other People, an original film with a clear basis in When Harry Met Sally… dynamics. It follows Jake (Jason Sudeikis) and Lainey (Alison Brie), who hook up once in college before unexpectedly reuniting over a decade later at a sex addiction meeting. Jake is a compulsive (if high-spirited and charming) womanizer and cheater, while Lainey’s compulsions focus on a single, toxic relationship with an attached guy; they strike up a friendship and attempt to keep it sex-free as they try to heal their romantic lives. That set-up alone is reason enough for awards-watchers to dismiss Sleeping With Other People from serious consideration in a category like Best Director. This kind of movie, if it does get any kind of recognition, tends to be honored for its writing, and Headland is, indeed, an excellent writer of emotionally honest scenes punctuated with crisp, self-aware but never smarmy banter.

But it’s worth remembering that movies are not solely writing, and the reason Sleeping works as well as it does—why it’s more than the sum of its laughs—is Headland’s assured hand behind the camera. It’s not just that Headland provides her actors with good dialogue and, it would seem, does a fine job guiding their delivery of it. She also creates physical space for Brie and Sudeikis onscreen, individually and as a quasi-couple. When the movie re-introduces the present-day version of Jake after its college-set prologue, Headland stages a scene wherein he attempts to chase down his sorta-girlfriend and talk her down from her apoplectic rage over his infidelity. It’s the first of several scenes that make great use of actual New York City locations as settings, rather than romantic landmark check-boxes.

When the film sends Sudeikis hurtling through the frame, both at regular speed and in slow motion, the people and cars he has to barrel past feel like real obstacles, not comic detritus. Headland’s dialogue is funny and sometimes elaborate, but she roots her characters in the real world. So the obvious thing to do to create a feeling of urgency in this scene would be to use jittery, clearly handheld cameras for faux-realism. Headland, though, lets the scene between Jake and his jilted lover play out in takes slightly longer than the usual back-and-forth cuts. They’re not bravura, technically complicated shots, but by keeping passing cars in the frame throughout the conversation, Headland both sets ups and makes semi-serious (if still amusing) the moment when the woman pushes Jake into the path of an oncoming cab.


Headland employs unfussy long-ish takes like this throughout the film—important for a movie about intimacy. The first and most substantial scene between Lainey and her longtime hook-up Matthew (Adam Scott) winds up with the two of them fucking on the desk in his office. Most of the actual sex also plays out in a single shot (with one early cutaway to the office door, ajar), and Headland captures white glints of sunlight coming through the window in the background, giving the moment lighting that’s both dreamlike and a little bit harsh. The “wrong guy” is a stock character in a romantic comedy, but this particular romantic comedy actually makes an effort to convey both what’s wrong about this guy and what feels right about him in the moment, all at once, in a matter of minutes.

Those cues connect to Headland’s direction of a pivotal first-date scene between Sudeikis and Brie. It ends with them deciding to just be friends, but the way Headland’s camera begins the scene by tracking along with them through the New York streets tells a different, more romantic story. During their first re-connection scene earlier in the film, Brie exits the frame, leaving Sudeikis standing there alone. In this one, Headland holds her shot long enough to keep Brie’s exit from their street-corner conversation in-frame, emphasizing the pair’s connection and in the process capturing one of the more realistic New York street-crossings (“I’m going for it!” Brie cries) in recent film.


Sleeping With Other People is full of these moments where Headland augments her story visually: a wordless scene where Lainey desperately runs after an oblivious Matthew on the New York waterfront; an overhead shot of Jake and Lainey sharing a bed with maximum platonic longing; the way the music kicks in and the camera doesn’t blink during a crucial fight scene. A few of these would qualify as nice touches; put together, they constitute excellent filmmaking. The less visual aspects of Headland’s direction sing, too: She helps Brie and Sudeikis to career-best performances, maintains a crisp pace, and either directs the dialogue scenes to sound natural or allows the actors just enough improvisational leeway to goose them.


This is not the kind of directing that gets a lot of attention. Its technical flourishes are relatively subtle, and casual moviegoers indeed might not notice (at least not consciously) the difference between Headland’s skill and the high-energy floundering that characterizes most rom-coms. But it’s a major reason this movie feels smarter, more bittersweet, and more lived-in than its bigger-name competition. Sleeping With Other People also didn’t reach a particularly large audience during its theatrical release in September. But the Oscar voting body is made up of filmmakers, with the Best Director nominees determined by other directors; those people should take notice when a filmmaker gives a familiar genre such thoughtful treatment. Nothing in Sleeping With Other People is stunning the way sequences in recent movies from George Miller or Steven Spielberg are stunning, which might matter more if the Academy weren’t totally fine with throwing Oscars and/or multiple nominations to journeymen like Stephen Daldry, Ron Howard, or Tom Hooper. Similarly, if Ridley Scott can be in the awards conversation this year for a coverage-heavy, competently assembled crowdpleaser like The Martian, a director like Headland—personal, distinctive, accessible—ought to be in the mix as well, for making a romantic comedy look as effortless and heartfelt as an old classic of the genre.

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