100 Best Grown-Up Comedy Films

A young bisexual woman attends a shiva, caught between her parents and their expectations, her ex, and her sugar daddy. Rachel Sennott’s Danielle is yet to find her path in life and everyone is determined to remind her of that. Taking place almost entirely in real-time, the film’s sharp wit is contrasted with constant anxiety, complemented by Ariel Marx’s horror-like score, full of discordant pizzicato that sounds like every last bit of sanity snapping. 

It’s a sex-positive take on 20-something life, treating bisexuality as wholly unremarkable and passing no judgment on Danielle’s sugar daddy income. Its specificities about Jewish customs and traditions are non-exclusionary, while its social claustrophobia is achingly universal. It’s comforting in the way it portrays the social horrors we all face, the feeling that everyone but you has life figured out, and that – ultimately – those who matter will pull through, eventually. One of 2021’s best.

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.

Don’t be fooled by its obvious parallels to Ghost (not a bad film, but a very different one): Truly, Madly, Deeply isn’t much concerned with the supernatural logistics of its back-from-the-dead-boyfriend premise, and it doesn’t feature any psychics or murders, either. In fact, there’s an argument to be made that everything that takes place here happens in its protagonist’s imagination — that’s how much it ignores the ‘how’ of it all.

Instead, this deeply warm rom-com from the great Anthony Minghella grapples head-on with the emotional challenges of grief and moving on. Juliet Stevenson’s performance as the bereft Nina is up there as one of the most moving portrayals of loss the screen has seen, and not just because of how believable her intense cry-acting is. When she realizes her deceased boyfriend Jamie (Alan Rickman, as seductive and sardonic as always) has returned to the land of the living, her euphoria brings to aching life the dream that everyone who’s ever lost a loved one must surely have dreamt: how joyous it would be to see them again. Blending such raw observations with wry humor — and anchored by two leads with genuine chemistry — this is a profoundly moving and rewarding movie.

Martin Scorsese had just spent a year prepping for The Last Temptation of Christ when Paramount Pictures unceremoniously pulled the plug on the movie just one month before production was due to start. After Hours was Scorsese’s way of exorcising all that disappointment and frustration, and you can feel it: this black comedy vibrates with manic intensity as it charts a night from hell in the life of Paul (Griffin Dunne), a somewhat scuzzy yuppie living in ‘80s New York City.

In keeping with its title — which suggests the movie is suspended in temporal limbo — After Hours feels like it takes place in some mythological hellscape, a demonic underworld in which everyone Paul meets has been sent forth with the express mission to make his life more miserable. Surreal coincidences pile up, deepening his paranoia and turning his simple goal of returning home into a labyrinthine quest for survival on the deserted, rain-soaked streets of SoHo. It’s the kind of celluloid nightmare that terrorizes and thrills you at the same time (a la the Safdie brothers’ best works, which draw inspiration from After Hours). Only a director of Scorsese’s caliber could turn profound professional disappointment into such a win as this.

Here’s a biopic that focuses on capturing the feel of the era it depicts, rather than all the facts — and is all the better for it. 24 Hour Party People takes the same punk approach to storytelling as its subjects did to music, playfully throwing off the dull constraints that often make based-on-a-true-story movies feel like uninspired celluloid translations of a Wikipedia page. 

In the film’s opening scene, Steve Coogan’s Tony Wilson breaks the fourth wall to address us directly and semi-spoil the movie’s ending. But it doesn’t matter, because the ride is so fun: we’re taken on an immersive trip through the heyday of the Manchester music scene: the births of Joy Division, New Order, the Happy Mondays, and Wilson’s Factory Records label and legendary Hacienda nightclub, an incubator for acid house and rave culture. The era’s hedonism is brought to life by the movie’s frenetic editing, documentary-style cinematography, and strobe-heavy visuals. For all its onscreen anarchy, though, the movie remarkably never feels loose or self-indulgent. Its irreverence is grounded by the ironic filter of the meta filmmaking, which frequently breaks the fourth wall to draw attention to its own conceits. A refreshing rejection of biopic tropes, but also a thrilling transportation into and evocation of the Madchester era.

It starts off with a cinematic intro sequence, flexing a big budget standup show that you’d only expect from a Hollywood star like Adam Sandler. But there are also elements of “lines being blurred,” with the pre-show frenzy backstage being carried over onstage. With a bizarre atmosphere firmly established, Sandler delivers his set like what I can only describe as an upbeat Jake “The Snake” Roberts, nonchalantly talking about his bizarre everyday interactions. He also delivers many of these stories in quick song format, with lyrics that sound like someone muttering under their breath about their grim day (or life). Just a fun, odd, and even emotional storytime with Adam Sandler.

The Fundamentals of Caring is an offbeat comedy/drama starring Paul Rudd as a man attempting to overcome his looming divorce by becoming the caretaker for a teenager with muscular dystrophy (Craig Roberts, Submarine). The two develop an unconventional relationship based largely on sarcasm and profanity, delivering many laugh-out-loud moments, while also slowly exposing the pain each is carrying inside.

Together, at Ben’s urging, they embark on a road trip across the western United States for Craig to see the world. It’s somewhat formulaic but fun and touching road movie that covers much familiar ground, but also offers a fine illustration of caregiving, personal growth, and emotional healing. Paul Rudd is as good ever, and Roberts is utterly superb. One of the best movies on the Netflix Originals catalog, and an undeniable winner, all-in-all.

Four Lions is as black and as dark as a movie can ever get, mixing cultural relevancy with humor and ridiculousness. It is insensitive to Islam, insensitive to terrorism and insensitive to the viewer. But it is hilarious. The director spent three years talking to Imams, terrorism experts and basically everyone. The result? A legit 97 minutes that will dazzle even extremists with its knowledge of Islam and the accuracy of its lines. Needless to say that it will upset quite a few people, but that is always a good sign for black comedy movies, right?

Challenging, strange, and utterly captivating from start to finish, Sanctuary takes the relationship between a pathetic, wealthy man and a desperate, plucky young woman—a relationship built on consensual acts of sexual humiliation—and makes it so much more dynamic and entertaining than it has any right to be. The film takes place entirely in one hotel suite over the course of one night, becoming a series of increasingly absurd psychological scenarios, as the characters wrestle over ideas of power, shame, and identity by concealing and roleplaying various parts of themselves. It’s a wild take on several different genres that director Zachary Wigon is able to effortlessly weave together with excellent pacing, stunning visuals, and two truly committed performances from Christopher Abbott and a wonderfully unhinged Margaret Qualley.

A healthy mix of despair and self-deprecation has always been Bo Burnham’s signature, but Inside takes it to the next level. It’s a deconstructed film, rather than a simple one-night special; a one-man-show that constantly undercuts itself. Even more so, it sabotages its own immersive qualities and explores the depths of self-loathing by turning oneself into comedy material. Some may say, it’s a classic move, but the pandemic reality and Burnham’s unkempt look predispose us to embrace all the cringe (YouTube reactions), quirkiness, (the sock puppet), and frightening angst (suicide jokes) he puts forward. Emotional rawness and a polished DIY look fits the Netflix bill, but as far as the content goes, this one goes straight to the world heritage lockdown archives.