100 Best Grown-Up Comedy Films

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.

Rarely do we get horror movies that are as dedicated to toying with audience expectations as Barbarian. Even rarer is a horror movie that pays so much attention to setting, and how men and women approach and interact with physical spaces in different ways. It’s a film that’s ultimately about entitlement—except it’s delivered to us with jet-black humor and manic energy, shifting from romantic to ridiculous to raving mad. But with instantly charming performances from Georgina Campbell and Bill Skarsgård—and Justin Long doing a brilliant job playing an absolute jerk—Barbarian never leaves you grasping in the dark, even if it leads you deeper into hell.

At 80 minutes, Smoking Causes Coughing is another slice of perfectly paced absurdist fun from Quentin Dupieux, the zany mind behind Rubber (in which a car tire turns serial killer) and Deerskin, the tale of a motorcycle jacket that wants to rule the world. This time around, the protagonists aren’t inanimate objects: they’re Tobacco Force, a Power Rangers-style band of lightly idiotic superheroes who harness the toxic power of cigarettes to defeat Earth’s enemies, and are each named after one of their harmful components (Benzene, Nicotine, Mercury, Ammonia, and Methanol). They’re led by Chief Didier, a rat who inexplicably dribbles green goo — and, even more inexplicably, casts an intense erotic spell over Tobacco Force’s female members.

Smoking Causes Coughing leans deliriously, hilariously far into its absurdist premise. Citing a lack of “group cohesion,” Chief Didier sends the Force to the woods on a team-building retreat. While they swap “scary” stories over a campfire, however, a reptilian galactic supervillain plots to put Earth “out of its misery” because it’s a “sick planet” (can’t really argue with that). Full of insane plot twists and without a tired trope in sight, Smoking Causes Coughing never approaches the realm of predictability — no small achievement in this era of superhero fatigue.

This HBO mockumentary is part-pastiche of the mythologising sports documentary, part-zany comic creation of its own. Tour de Pharmacy tells the incredible untrue story of the 1982 Tour de France, the most chaotic iteration of the race that never happened. Of the original 170 cyclists, all but five were disqualified for bribing the deep-in-debt president of cycling’s governing body (Kevin Bacon), leaving only Italian-a sensation-a JuJu Peppi (Orlando Bloom); secret female racer Adrian Baton (Julia Ormond and Freddie Highmore); frustrated nephew of Jackie Robinson, Slim (Daveed Diggs); a roided-out Austrian (John Cena); and Marty Hass (Andy Samberg), a Nigerian cyclist despised by his country.

Tragedy, scandal, and surprising romance unfold across the documentary’s chronicling of the race’s 21 stages, with plenty of digressions along the way — from a riotous interview with the head of the sport’s anti-doping agency (played by Nathan Fielder) to an animated explanation of red and white cells that devolves into a surreally bloody civil war. The humor zooms between the high-brow (French New Wave references delivered by JJ Abrams) and the R-rated from scene to scene, making this breezy mockumentary a wild ride of its own.

Of the many violence-inflected black comedies that Pulp Fiction spawned, Grosse Pointe Blank ranks among the best. Though it’s patently inspired by Tarantino’s magnum opus — John Cusack plays a sardonic, amoral hitman, and the film features bursts of stylized violence and a retro soundtrack — it never feels derivative. The film finds its own identity as a quirky romcom when Cusack’s character, Martin Blank, returns to his hometown for a 10-year high-school reunion on the advice of his terrified therapist (Alan Arkin).

Martin is experiencing professional disillusionment as part of the quarter-life crisis that often takes hold when one realizes it’s been a whole decade since high school. His profession puts a darkly comic spin on that convention, but the film doesn’t treat that element entirely flippantly. Unlike Martin — and so many of the film’s Pulp Fiction-inspired brethren — Grosse Pointe Blank isn’t nihilistic, but quite sincerely romantic. Its hybrid nature and surprising heart come to the fore in Martin’s renewed relationship with the girlfriend he jilted at prom: Debi (Minnie Driver), now a ska-loving radio DJ. Cusack and Driver have sparkling chemistry, which makes the sincerity with which their characters grapple with the possibility of a second chance at happiness all the more absorbing to watch.

After Jackie and Spencer, the dark satire El Conde is a surprise new entry in Pablo Larraín’s stacked filmography. Already, the film has prominent differences– it’s shot in black and white, starting with narration from an unseen and posh Englishwoman that makes the film’s events feel like entries in Bridgerton’s scandalous newsletter. The subject is far from the beloved wives of presidents and princes– it’s centered around a notorious Chilean dictator who remains unpunished for his crimes. However, as his fictional vampire version deals with his rightfully ruined legacy, El Conde proves to be a witty satiric twist to Larraín’s usual themes. Through familial squabbles over ill-gotten wealth, confessions and exorcism conducted by a nun, and certain foreign interventions, El Conde paints an everlasting greed that continues to haunt Larraín’s homeland.

The Romanian New Wave’s predilection for bleakness gets a tongue-in-cheek dig in this buddy comedy from the same country: “Romanians are bad at making movies,” Pompiliu (Alexandru Papadopol) complains. “They only show doom and gloom.” Indeed, the premise here could easily make for a miserable movie: three hapless working-class pals win a multimillion lottery jackpot but lose their ticket — and, with it, the chance for Dinel (Pedro Pascal-lookalike Dorian Boguță) to pay off the mafia don that’s holding his wife hostage in Italy.

But Two Lottery Tickets takes a decidedly droll view of their predicament. Part of that approach is achieved via the trio’s characterizations: they’re all goofy in different ways, from the ridiculous conspiracy theory-spouting Pompiliu and the gullible Dinel to sleazy chancer Sile (Dragoș Bucur). The rest of the film’s breezy comic tone comes thanks to their amusingly convoluted journey to retrieve the ticket, which they believe is in a bag that was stolen when Dinel was mugged by two thugs. These many segues implicate a cross-section of Romanian society into the film, making it a wry social commentary in places. Mostly, though, Two Lottery Tickets has modest ambitions — to be, simply, an enjoyable comedy — a goal it surpasses thanks to its absurdist humor and pitch-perfect performances.

You don’t have to have seen a single game of tennis to enjoy this mockumentary about the longest match that (n)ever took place in the sport’s history. Andy Samberg plays Aaron Williams, the mullet-sporting adopted brother of Serena and Venus (whose family “reverse Blind-Sided” him) made immortal by his record-smashing, week-long battle with posh, dim-witted English prodigy Charles Poole (Kit Harington) at Wimbledon. Things only get more riotously ridiculous from the premise: the team behind sports spoof Tour de Pharmacy chronicle the winding journeys the rivals took to that climactic seven-day showdown, from forays into the world of innovative underwear design to stints in Swedish jails, by way of a surreal tangent into the storied faux-history of courtroom sketch art. Suffice it to say: the tennis isn’t really the point here.

Real-life figures from the sport (including Serena Williams and John McEnroe) ground the spoof in enough reality to make the zany humor pop, with the comedy coming from a very game Fred Armisen, Michael Sheen, Lena Dunham, Will Forte, and Howie Mandel. With eccentric humor in spades — from the puerile to the surreal — and a lean runtime, 7 Days in Hell packs in as many dizzying jokes as Aaron and Charles do volleys in their absurd history-making rally.

Generation-centric comedy is often of the “kids these days” variety — in which comedians make uninspired jibes about the youth of today while spectacularly lacking self-awareness of their own — but twenty-something stand-up Leo Reich thankfully upends that trend with his self-lampooning debut show. Reich takes a risk by unabashedly casting himself as a self-absorbed nepo baby in the opening — narcissism as a bit can become grating pretty quickly — but his perceptive abilities and readiness to both embody and commentate on Gen Z stereotypes are the saviors of this hour-long comedy special.

Stand-up isn’t the only medium he makes use of: the show is also part-musical, as Reich belts out wry musings on the contradictions of his generation — at once self-loathing but tending towards narcissism, cripplingly self-aware but no more enlightened for it — at intervals throughout. If there’s anything to lament here, it’s that Reich’s main character syndrome is so effectively paired with the doom-and-gloom context he paints (as he puts it, he’s spent way too much of his youth Googling “death toll”) that the show’s aftertaste is a little too bitter — but then again, nihilism is another characteristic typically associated with zoomers, so you could argue this is simply supreme commitment to the bit.

Demonstrating that a great stand-up routine should always stem from strong writing first and foremost, Brian Simpson makes common subjects for ridicule feel fresh again—just through how clever his writing is. Simpson seems to position himself from the same place where more controversial comedians punch down at women and at queerness. But he manages to push against expectations by keeping his focus on those who normally don’t get the brunt of the criticism, or by drawing us toward broader cultural problems that make people act the way that they do. None of this is all that novel, of course, and Simpson does end up dwelling on certain subjects for too long. But every line he speaks feels considered and is deployed with the perfect matter-of-factness, keeping the laughs consistent without ever complaining or intentionally trying to provoke.