The 50 Best Indie Comedy Movies

There are only two main characters in Good Luck to You, Leo Grande: Nancy, a retired teacher who was recently widowed, and Leo, an adept sex worker with a mysterious past. They’re almost always in one place and work on a single goal: pleasure. But despite the seeming monotony, the movie is crackling with wit and sensuality every step of the way. It doesn’t waste any time getting to the heart of the matter. Nancy and Leo go back and forth about their past, with Nancy divulging much about the stigma of aging and Leo about the stigma of sex work. They also dive into the shame attached to pleasure, ultimately revealing more than just their naked bodies to each other and to the audience.

My Old Ass has a very simple premise, one it doesn’t even take the effort of explaining. For whatever reason, 18-year-old Elliot meets her 39-year-old self, and they talk at length about life. Naturally, older Elliot gives her younger self some advice to improve her life. But she also gives her a grave warning: under no circumstances must she be with a man named Chad. The film then follows younger Elliot as she tries to heed her advice and learn a lot about life in the process. Now, on paper, that may sound like sentimental schmaltz, but the two actresses playing Elliot—Stella and Plaza—are what make the film so grounded and enjoyable. Stella is bursting with life and energetic humor, while Plaza delivers her signature stoic wit. That’s not to say she’s lifeless though. By the time the climax rolls in, you’ll be struggling to keep the tears in.

This is a star-packed movie about two brother assassins played by John C. Reilly and Joaquin Phoenix, and starring Jake Gyllenhaal. You might have read the book of the same name, and it is always hard to make a great film out of a great book but the brilliant director of A Prophet Jacques Audiard has done it (again). He is aided by a superb darkly comic script and fantastic acting from the entire cast. Audiard is French, but his take on the American Western is filled with epic violence but also witty dialogue, brotherly love, and male camaraderie.

On the one hand, American Fiction is a razor-sharp satire that pokes fun at the hypocrisy of the literary and entertainment industry. It’s only when Monk (Wright), a genius but esoteric writer, decides to pander and give in to what publishers have come to expect from Black authors (that is: trauma porn) that he is finally celebrated for his work. But on the other hand, the film is also a tender family drama. Monk sells out, as it were, partly because he’s fascinated by the stupidity of decision-makers and supposed intellectuals, but mostly because he needs to pay for his ailing mother’s care. His relationship with his siblings and deceased father likewise informs much of his character, and they complicate what could’ve been just an intellectual approach to a social issue. This is an educational and entertaining film, yes, one that looks at the complex intersection between identity, craft, and profit. But it’s also an empathetic film, told with a big heart and a surprisingly light touch.

Other People’s Children wrestles with some very tricky life experiences: bonding with a partner’s child in the agonizing knowledge that that attachment is entirely contingent on the fate of your romantic relationship; being a woman of a certain age and wanting a child but becoming keenly aware of the ticking of your body clock. For all the sharp points of pain the movie zones in on, though, there is remarkable cheerfulness in it, too. Writer-director Rebecca Zlotowski captures a wide spectrum of mood here, fusing lighthearted laughs and swooning romance with bitter disappointments and grief in a way that feels organic to life itself. The buoyant moments don’t undermine the sincere, intelligent consideration given to Rachel’s (Virginie Efira) perspective as a woman navigating a situation for which there are no real rules, and vice versa — because the film considers her as a whole from the outset. Neither reducing Rachel to her childlessness nor ignoring its emotional impact on her, this is a deeply empathetic movie that never questions the completeness of its protagonist’s life.

At the same time a fun, crazy, and meaningful movie about Malcom and his friends, high school teenagers and proud geeks who suddenly find themselves immersed in the underground LA drug scene. It’s a 2015 Superbad meets Boyz in the Hood. But in its essence it mostly resembles another beautiful film, Juno, in the way it evolves around a character played perfectly who you get to know, agree and disagree with, and ultimately learn from and relate to. Above all it’s an outright enjoyable film, a smart one too, with a great soundtrack to boot.

Before he developed his signature dollhouse visual style, Wes Anderson made his feature debut with this lowkey, heartwarming, and decidedly not-symmetrically-perfect comedy about a bunch of misfits. Bottle Rocket isn’t as much of an outlier in its director’s storied filmography as might initially seem, however. Written in partnership with college buddy Owen Wilson — who, along with brothers Luke and Andrew, made his acting debut here — the film is delightfully offbeat and unexpectedly moving in the way we’ve come to expect from Anderson.

Dignan (Owen Wilson) and Anthony (Luke Wilson) are two drifting, boyish twenty-somethings, although only Anthony seems aware of his directionlessness, as Dignan has graciously developed a 50-year life plan for the two of them (complete with hilariously vague bullet-points such as “Make wise investments” and “Own multiple accommodations”). The means to these ambitious ends is a life of crime — specifically, pulling off grand heists. But Dignan’s meticulousness hasn’t accounted for distractions, and his madcap scheme falls at the first hurdle when Anthony falls in love with a housekeeper at the motel they hide out in (Lumi Cavazos). Their sweet romance is one of the film’s many delights, as is its barrelling deadpan humor, which never betrays the warmth of the Wilson brothers’ heartwarming depiction of ride-or-die friendship.

Given the title, it isn’t surprising that Falling in Love Like in Movies would be a metanarrative with the main romance mirroring the filmmaking and the filmmaking reflecting the main romance. It’s a familiar approach, and at first, Falling seems to follow the inevitable ending where the couple falls in love, but right on time, in around Sequence Four, writer-director Yandy Laurens chooses a more honest, less chosen path– a path that plenty of previous romance films hasn’t examined– that still falls within the eight sequence screenplay structure Bagus talks about. While Bagus is pitching his film to Hana, and to his producer, Jatuh Cinta Seperti di Film-Film pitches a new way of thinking about love, grief, and of course, filmmaking.

Frances (Greta Gerwig) lives in New York – but not the glamorous NYC of Woody Allen movies. Taking place primarily in the gritty and rapidly gentrifying North Brooklyn, the black and white film paints a picture of an extended adolescence. Focusing on the goofy and carefree Frances, who loses her boyfriend, her best friend and her dream of being a dancer. She moves in with two guys, both of whom are more successful than her, and becomes even more determined to fulfil her goals, impractical as they may be. Fans of HBO’s Girls and other odes to not being a “real person” yet will love this film.

Many comedians use humor as a way to ease into more serious subject matter, though there always exists a risk that a comedy special can skew too far down the silly or the self-reflective route. Mike Birbiglia has come about as close to the perfect balance as possible, in this recording of his one-man Broadway show at the Vivian Beaumont Theater. Key to this is the fact that Birbiglia tells one very cohesive story throughout these 77 minutes, frequently branching off to other humorous anecdotes but always returning with a pensive self-consciousness to the real possibility of him dying sooner than he’d want.

This filmed version of Birbiglia’s show doesn’t give a full idea of its multimedia qualities (Birbiglia occasionally has words and images projected onto the curved screen behind him, which he also physically interacts with), but the comedian’s sincere style of storytelling more than makes up for the lack of audiovisual tricks we’re permitted to see. And don’t get it confused: this is a very funny stand-up special, whose jokes always come from the most unexpected places—it also just happens to contain some truly moving moments that come out of nowhere, but make total sense alongside all the laughter.