Movies to Watch With Dark Comedies

Twinless starts off something like one of those quirky indies in the 2010s about awkwardly navigating grief and sharing that with someone, unexpectedly. Roman meets Dennis in a support group like The Fault in Our Stars, though with a sibling dynamic a la The Skeleton Twins, filling the void of losing their other half. It’s wholesome, it’s cute, and Dylan O’ Brien and James Sweeney have an instant chemistry that makes their friendship easy to root for. But after the twenty minute mark, this comedy veers into an unexpected direction. For the sake of spoilers, we won’t elaborate, but Twinless cleverly twists what could have been a millennial mumblecore drama into a clever, provocative Gen Z dark comedy that isn’t afraid to go there. Twinless is truly one of its kind.

With a title like this, it was expected that Do Not Expect Too Much from the End of the World would be critical of today’s current circumstances, but the film takes a more startling approach. Radu Jude’s longest narrative feature is a day in the life of a disgruntled, underpaid production assistant, and as she drives between interviewees injured from work accidents, the film alternates between the black-and-white, terribly mundane reality, her Tiktok-filtered satirical rants as Bobiță, and an old colored film of a Romania decades past. It’s a cynical depiction of how vulgar it is to be alive today, but it’s also more honest as Jude refuses to cling to the past.

Amongst the google searches for this one you’ll find “Is Slotherhouse a real film?” and that says a lot. When the first poster and trailer dropped, I suspected it the work of AI, but now that the film is out on streaming, we should be glad it exists. A ludicrous horror-comedy that hits all the right notes in gore, cringe, and puns, Slotherhouse is quintessential fun cinema. It may be set in a college where internalized misogyny is completely off the charts as young women bruise and batter each other’s egos in service of the queen bee Brianna (Sydney Craven) and may attempt just a tiny bit of character development to keep the ball rolling, but honestly, who cares? It’s a film that completely leans into the absurd, the over the top, the ridiculous, and it does it surprisingly well.

Sometimes, especially when you’ve gone without it for so long, you would do anything for a shred of respect. LaRoy, Texas depicts exactly that, with a store owner Ray being so unwilling to stand up for himself that his wife cheats on him with his brother, who steals from the family business. It’s a terrible situation to be in, of course, but it’s played out in a dry, comedic way, as detective-wannabe Skip pokes on the wound when trying his best to solve the case, and as each surprise reveals how terribly incompetent the small town deals with things. While it doesn’t quite compare to the neo-Westerns of Coen brothers it’s inspired by, LaRoy, Texas is both fun and tragic, and a promising debut for writer-director Shane Atkinson.

They Cloned Tyrone is a genre-bending gem. It combines Deep State conspiracy theories with sci-fi and social commentary, all while looking like a futuristic 1970s Blaxploitation film. It’s outrageous good fun and pleasing to look at (here is a film that knows how to properly light Black actors), but there are times when it feels too far fetched. The science can get wonky and its commentary on gentrification lacking, but all is forgiven when you have such a strong trio of leads. One of the smartest things They Cloned Tyrone does is pair Boyega with Teyonah Parris, who plays the call girl Yo-yo, and Jamie Foxx, who plays the pimp Slick Charles. They have a fun-loving no-nonsense chemistry about them that makes them easy to attach to and root for. They’re also just very funny, which might be expected of Foxx but it comes as a pleasant surprise for Parris, whose popular turns in Mad Men and WandaVision prove that she’s been severely underutilized as a comic.

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.

The colloquial phrase “May-December” refers to romantic partners with a large age gap, but leave it to Todd Haynes to craft a poetic and unsettling world out of this (slightly troubling) banality of life. His new film is loosely based on the real case of Mary Kay Letourneau, who in 1997 was convicted as a sex offender after being caught having a relationship with a minor, a student of hers, 12 years old (22 years her junior). May December begins twenty years after the tabloid scandal surrounding the marriage of Joe and Gracie has died down. Elizabeth, an actress, is conducting research in preparation to play Gracie in a film production, but she doesn’t know what to expect. Alongside her, we are welcomed into the family home, meet their teenage children, sit through their family dinners, marvelling at the levity and nonchalant atmosphere in the air. Something is missing, or at least that’s what Elizabeth suspects. A psychological drama-thriller-black comedy, May December is impossible to pin down. A profound film on human confusion, identities, and past traumas, it unites two of the best Hollywood stars, Julianne Moore and Natalie Portman, in a delightfully eerie play of doubling and revelations.

When Mikey Saber’s porn career takes a dip in California, he returns to an estranged wife in Texas, where he meets new and old friends alike and attempts to rebuild his life through a couple of odd jobs. Though Mikey eventually earns his keep, his vanity and eagerness to succeed at all costs threaten to get the best of him.

All this happens against a vibrant backdrop of local sights, beautifully lit and framed by director Sean Baker (The Florida Project, Tangerine). Quaint, naturalistic, and ever-so-subtly political, Red Rocket is another great entry into Baker’s impressions of the vexed American Dream.

Given today’s access to cameras, it’s so easy to peek into the lives of other people. Sometimes those peeks seem much more exciting than our entire lives, but as most people know by now, what we see on screen can be so different to what’s really happening. Rather than social media, however, the two broke nobodies in The Great Buddha+ get their entertainment from the dashboard camera of their rich and famous boss, Kevin, though the recordings eventually reveal a darker side to the artist-philanthropist business owner. Alternating from their black-and-white lives to their boss’ colorful one, this dark comedy satirizes that gap between classes, the ones being watched and the ones who could only watch, with the narrator, and sometimes the characters, helpfully explaining on occasion what you’re seeing on screen. The Great Buddha+ gleefully mocks its ensemble, while still being cognizant of the real injustices they face. 

This artistic Australian coming-of-age drama stars Eliza Scanlen (Little Women, Sharp Objects) as Milla, a teen from a dysfunctional family. The father is a psychologist and the mother suffers from depression, so he medicates her under the table. Meanwhile, Milla, a 16 year old, starts dating a charismatic almost-homeless 24 year old drug dealer. Unusual circumstances make the family tolerate the relationship in this story where every character feels like the main one. 

If you’re looking for something different, you will love Babyteeth. Something happens to Milla in the 10 minute mark that descriptions and reviews online all mention – but is definitely a spoiler. Just know that it’s not all romance and coming-of-age, there is slow-burning darkness to this movie. 

In cinema’s fight against AI, we’ve seen sci-fi spectacles, action-packed stunts, and the belief in sheer humanity that helps us win the day. But perhaps it’s that optimism that has led us here. Perhaps that’s why Good Luck, Have Fun, Don’t Die chooses to depict a bleakier, kookier version of this battle. Still, despite the hopelessness of it all, director Gore Verbinski has a lot of fun dumping a time-travelling Sam Rockwell in a full LA diner taken unawares, pushing him on a chaotic mission with unpredictable steps and surprisingly moving moments along the way. Thanks for the warning! We hope that certain AI tech overlords would hear it.

In The Kid Detective, Adam Brody stars as Abe Applebaum, a once-beloved child prodigy turned pathetic P.I. stuck in the glory days of his past. At 32 years old, he’s still solving petty mysteries and coasting on his parents’ money, but things start to change when he is finally dealt with a real, adult case: a murder that confounds even the local police. As Abe uncovers more details about the case, he also unwittingly finds a connection to his traumatic past and begins a long-overdue coming-of-age journey. 

Released during the first year of the pandemic, The Kid Detective understandably flew under the radar when it first came out, garnering sufficient critical praise but not enough fanfare. It will no doubt find a second life among film lovers, though; it’s too smart and riveting to go unnoticed. Most impressive is how director Evan Morgan, in his feature debut, deftly balances multiple genres in a movie that often feels as if Wes Anderson’s The Royal Tenenbaums, Roman Polanski’s Chinatown, and modern stoner humor were somehow rolled into one. The gags consistently amuse, the drawn-out mysteries pay off, and the human element persists throughout. Adam Brody, himself a kid celebrity back in the day, expertly carries this delightful and sobering film. 

Robin Hood might be a centuries old folk hero, but his reincarnations seem to pop up in real life, including the true story behind Dying to Survive. Alternatively translated as I’m Not A Medicine God, the modern day Chinese iteration is initially less concerned over the common good and more concerned with money. It makes for a much more humorous take, as the ordinary peddler bribes, smuggles, and asserts his desire for profit, but it also sets up the real desperation created by a medical drug industry that hopes to incentivize research and protect consumers, but inadvertently blocks the very people that needs said drugs. Dying to Survive might focus more on the smuggler than critiquing this conundrum, but nonetheless it understands the real recurring tragedy that modern life can’t seem to completely solve.

Remarkably for a movie about women being shunned and exploited by those more powerful than them, I Am Not A Witch is often wryly funny. That’s because this satire about Zambia’s labor camps for “witches” is told with a matter-of-fact-ness that brings out both the heartbreak and absurdity of the film’s events. The bitter gravity of the predicament nine-year-old Shula (Maggie Mulubwa) finds herself in — she’s been accused of witchcraft on the back of some very flimsy evidence — is never glossed over, but neither is its farcicality. Appropriately for its subject, there are also touches of magical realism here, notes that elevate the film into something even more complex than a wry commentary on this morbidly fascinating form of misogyny. This hybrid tonal approach is executed with the kind of fluidity filmmakers might hope to one day master late on in their career — which makes the fact that this is director Rungano Nyoni’s debut all the more extraordinary.

After a man spends his entire trust fund, what is there to do for the poor bachelor? One might think he might try to get in the good graces of his family, or perhaps work for a living (the horror!). Instead, Henry Graham decides he must marry a wealthy woman in A New Leaf. What occurs next is a witty turnaround of the gold-digger tale, as his initial straightforward plan to marry-then-murder awkward heiress Henrietta Lowell accidentally turns him into a better person, or at least, a person with the willingness to do something other than spending. Pitting Henry’s self-interest against Henrietta’s love for botany and her disinterest in her own inheritance, A New Leaf crafts a clever comedy with a cynical yet charming romance.

La Cocina is pretty chaotic. Amidst the hectic rush hour at The Grill, writer-director Alonso Ruizpalacios brings a group of tired, impoverished workers that yearn for a better life into a cramped kitchen in America that gets flooded with cherry cola halfway through the movie in an outstanding long take. While some scenes still retain its monologue heavy quality, it’s impressive to see how they adapted the stage play to film in its cast, multiple languages, and shots. The main protagonists, Raúl Briones and Rooney Mara, also deliver great performances. But what makes La Cocina ultimately work is how well it understands the power dynamics to push the story. La Cocina carries the perspectives of its ensemble characters with superb balance.

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.

This Eddie Murphy comedy had all the ingredients to be both a famous movie and an award-winner, but neither happened. It tells the true story of Rudy Ray Moore, a comedian who became famous for creating a character called Dolemite, a pimp, and who later attempted to make his own movie based on the same character. Murphy plays Rudy, but there are also other recognizable faces in supporting roles: Chris Rock, Wesley Snipes, Keegan-Michael Key, Snoop Dogg, and many others. It’s above all a funny movie, but being Eddie Murphy’s first R-rated movie since 1999, it’s also a realistic portrayal of both 1970s L.A. and the struggles of being a black filmmaker at the time.

Watch this if you like weird movies. And don’t be fooled by the first half, which serves just to set Jesse Eisenberg’s character and the monotone life he leads. It’s the calm before the storm, during which that character is attacked by a violent gang and decides to take self-defense classes in an unusual club. This is a movie about modern manhood and how it can lead to some pretty strange situations. Great performance from Eisenberg as usual.

Forgoing the typical catastrophic approach to the apocalypse, writer, star, and director Don McKellar opts for a grounded tone in Last Night, a film about the end of the world. In it, various Torontonians figure out how best to celebrate and mourn their final hours on Earth. While McKellar’s character Patrick originally planned to spend the day alone, he finds himself gravitating to Sandra (Sandra Oh), a stranger who he gets to know in a series of conversations.

Last Night is more like Before Sunrise than The Day After Tomorrow in that way, filled as it is with thought-provoking dialogue and interesting insights into everyday characters. Whether it was intentional or due to the obviously limited budget, the decision to leave out details like why the world is ending and how is a clever one since it allows us to hyperfocus on everyone’s psyche and inner workings. There is desperation, longing, and anxiety, but also relief, gratitude, and joy. 

If you’re watching it for the first time, you’ll be delighted to find surprise stars populate this lo-fi production—apart from McKellar and Oh, well-regarded auteurs Sarah Polley (Stories We Tell) and David Cronenberg (Crimes of the Future) also make welcome appearances. 

Murder is terrible, of course, but it proves to be surprisingly hilarious in Kind Hearts and Coronets. On top of all the ridiculous schemes Louis Mazzini cooks up, this ironic comedy of manners sets up its unfortunate deaths through Louis narrating his memoir in a detached tone, explaining away the deeds as if it was a natural consequence for the aristocratic snobs in his family. But the dry tone doesn’t quite conceal Louis’ wickedness. In fact, it highlights the horrible desires he’s dreaming of, poking at the fascination around British nobility without the usual melodrama these stories tend to have. It’s this brilliant twist that made Kind Hearts and Coronets so delightfully wicked.

Thunder Road is both a single-shot 13 minute short and a 91-minute feature-film expanding the story. Both are excellent and award-winning, but I really recommend the full experience!

Jim Cummings (above) is the director, writer, and main actor of this dark comedy. He plays a police officer having the worst day of his life as he tries to sing Bruce Springsteen’s Thunder Road at his mother’s funeral.

This sight is funny, and so is most of the story. But it’s also cringe-inducing, and because the main character is so sincere in his decline, will make you feel guilty about laughing so much. 

Murdering your spouse is bad, so it’s slightly bizarre how Drowning by Numbers has an unbothered, even amused, attitude towards its murders. Moments seem randomly placed, like the first scene of a girl jumping rope while listing the stars by name, and the film can be hard to follow, even if the production design and cinematography keep you drawn in. But as the film progresses, and Madgett’s son Smut enumerates the fictional games as if he was a historian of sorts, writer-director Peter Greenaway meticulously crafts a quirky, twisty crime comedy, where, like children’s games and the men in their lives, the murdering wives do what they do because they can get away with it. Drowning by Numbers cleverly plays with the way we treat folklore, structure, and rules, even down to the very medium Greenaway works with.

Visiting a relative can feel strange, because especially when the loved one you share is gone, the visit will inevitably bring up feelings of grief, nostalgia, and being stuck because of it. But no visit would be as strange as the 1977 cult horror classic House. It’s a classic not because it’s particularly scary– in fact, most of the time, the film is much more bizarre than terrifying– but because this grief manifests in the eccentric estate through unusually unrealistic, but undeniably stylish psychedelic visions that stem from the kind of nightmares one would get as a kid as well as the real-life devastation Nobuhiko Obayashi faced as a Hiroshima survivor. It’s because of these absurd images that House escapes explanation, yet still became Obayashi’s definitive work. Hausu is simply a film that you have to visit for yourself.

Familiarity breeds contempt, and Swedish Netflix’s new horror-comedy takes this idea to the extreme. Based on the novel by Mats Strandberg, who’s known as the Swedish Stephen King, The Conference is centered around a group of employees on their company retreat. With its ensemble, the film crafts a relatable dynamic, with the exact petty back-and-forth and the same exact corporate politics many adults have to deal with. It’s no wonder one of them snaps, and takes them out one by one. The film isn’t exactly new, with the decades’ collection of slashers all over the world, but this Swedish thriller is a fun take on it, with match cut transitions, quick paced sequences, and the gruesome murders of the group most adults spend time with – their colleagues. It’s an interesting watch as the world gets back to the office.

More than a decade before she made Toni Erdmann, German filmmaker Maren Ade turned her eye on a small-town school, a socially awkward teacher, and the inarticulate in between. Even with her debut, Ade showcased a talent for spotting the hidden comic potential of situations that can be wounding, turning vulnerabilities into power through comedy. The Forest For the Trees is a dilemma-film, in the ways in which it both invites and rejects identification with Melanie. A frighteningly optimistic person, she misreads most if not all social cues and finds herself in embarrassing situations. Even more, her devotion to making it all work, after moving away from the big city for said teaching job, is something a lot of viewers can recognize and support, but her borderline unlikeability is sometimes too hard to ignore. However, a majestic finale crowns the film with a scene that is worth rewatching again and again, like a dream you wish to appropriate for yourself.

Given the time period, it’s easy to see The Teacher as a satirical critique of the communist regime. Through the parent-teacher conference in a small high school, director Jan Hřebejk depicts a community shaken by the placement of a new teacher aligned with the Party. The new hire in question is nasty. While outwardly amiable, the subtle way she tries to extract favors, from simple repairs to hard-to-get medicine, feels terribly slimy as the kid’s grades are held in the balance. Zuzana Mauréry balances that two-faced dynamic with excellent skill, making her character someone we’d love to hate. And it all culminates into an intriguing ending that proves that while corruption has flourished under the regime, the following administration hasn’t done much to address it. The Teacher is a hilarious black comedy that isn’t afraid to bite.