From the screwball masterpiece His Girl Friday to the gem that is 9 to 5, some of the most illuminating portraits of ambitious women are comically bittersweet, concerned with what it really feels like to move through rooms in which you feel like an outsider. Writer and star Mindy Kaling is no doubt aware of this history, and likely referenced it in the course of mapping out her own tale of workplace exclusion, Late Night. But where her movie’s cinematic predecessors shined — in balancing the grudging reality of modern workplaces with the comedic gusts of unruly women — Late Night feels left in the dark.
I really wanted to like this movie. I’ve been hungry for risible depictions of determined women navigating their careers on the big screen. Late Night seemed to be the answer, hand-delivered in the form of a well-suited Emma Thompson, dressed as though she’s pulling from Bowie’s Thin White Duke era. Thompson plays Katherine Newburry, an iconic TV host who speaks with the kind of nonchalant brutality you might expect from a woman who’s had to work her way up a male-dominated ladder. (“That would mean so much more coming from someone with a job,” she says to the underling who called out her internalized sexism, after firing him.) Kaling plays Molly Patel, who has left her job in a chemical in Pennsylvania to join Katherine’s writing staff in New York City. She has no experience in the field, but Katherine’s show is desperately trying to diversify its all-white writers room, so she finds herself in her dream job.
Molly is starstruck in the presence of Katherine, who hardly proves an easy mentor. Katherine is just as vibrant and intelligent as she is thoughtless and obtuse. For example, she has a penchant for nicknaming her staff in the form of numbers because she refuses to learn their names. It’s only when she learns that she’s going to be replaced by a young, offensively crass male comedian (Ike Barinholtz) that she begins to lean on Molly’s skills. While she stumbles at first, Molly proves to be the perfect person to inject Katherine’s show with a fresher, more modern perspective. She urges the host to talk publicly about being an older woman in comedy. But as her suggestions pay off and she becomes more valued as a staff member, she starts to feel the envy of other writers on the team.
One of the true highlights of the film is the costuming. Mitchell Travers weaves a fascinating portrayal of the late-night host’s struggles through her wardrobe, and paints a detailed picture of Molly’s growth through the outfits she wears, too. Both characters’ performances are elevated by the deliberate choices made in terms of fashion, like the glittering, midnight-blue suit Katherine triumphantly dons later in the film. But even the film’s most charming character work is undone by the stale jokes that populate its script. Its understandings of race and privilege feels like they were gleaned from an HR PowerPoint in 2005. The resulting stand-up scenes are downright leaden. Perhaps inevitably, Late Night is too interested in showing both sides of the issues at hand — racism and sexism in the workplace — that it lacks the bite necessary to pull off any reconsideration of the recent workplace dynamics it sets out to assess.
In one scene early in the film, Molly enters the writers room to find that all the chairs are occupied. As a result, she is forced to empty a trash can and create a makeshift seat at the table. This sets the tone for her dynamic with the other writers: their begrudging acceptance underscored by bullying, her unfettered excitement hoping to gently wear them down. To put it bluntly, Kaling is too kind to the white men of the writers room, and even to Katherine Newburry. Characters like Tom (Reid Scott) and Mancuso (Paul Walter Hauser) refuse to acknowledge Molly’s humanity, and no amount of feminist-hued humor can distract from that. But Molly takes it upon herself to change them anyway. She works tirelessly to make room for kinder, more earnest work relations and begins confronting her colleagues about their unacceptable treatment. Considering how more and more women are speaking out about toxic workplace environments in their own lives, it’s strange to watch a movie with such a pat message: It’s on the backs of characters like Molly to convince their oppressors of their humanity. In the meantime, they’ll just suffer until enlightenment is achieved.
It’s in watching Molly navigate this environment that something becomes apparent: We have no character context to help us understand the ambition that powers her through it all. We never see the aunt and uncle she lives with — only her niece in two spurts, an editing decision that makes it feel as if the side character was cut from a larger story line. Her romantic narratives are undercooked. We’re mostly at work with her, watching her get beaten down to the point of tears. There are a few grace notes, like the brief moment Katherine and Molly share discussing their experiences with depression, but the conversation leads us nowhere. There was space in this film for a rich weaving together of ambition, anxiety, and humor, but it never came to be.
In Late Night’s conclusion, Molly technically learns to nurture her ambition — to not to settle when it comes to her professional dreams. It’s a lesson I hope audiences learn too in watching the film: We shouldn’t have to settle for mediocre, feminist-tinged films like Late Night merely because we’re hungry for representation.