10 Best Cringeworthy Black Comedies Like ‘Friendship’ To Check Out Next

Friendship is a movie that satisfies you with its slow, awkward, and emotionally catastrophic unraveling. Directed by Andrew DeYoung in his feature debut, this black comedy offers peak social discomfort, indicts male loneliness, and presents the kind of obsessive bonding that makes you laugh, feel seen, wince, and maybe call your therapist. Tim Robinson stars as Craig Waterman, an awkward marketing executive whose life is falling apart. Enter Paul Rudd’s Austin Carmichael, a charming weatherman with a punk band and a liking for mushroom hunting. Their friendship starts with beers and tunnels and ends with boundary violations and one of the most cringeworthy group hangouts ever committed to film.

The brilliance of Friendship lies in the way it balances total ridicule with genuine pathos. Craig is a needy and vulnerable person. And while you watch him be utterly delusional, you relate to him and root for him. Austin, on the other hand, is more layered. He’s charming but hollow. A man with a knack for performative connection. The movie’s humor, rooted in social missteps and weaponized niceness reminds you of your own everyday interactions. This lived-in quality and subjective direction is what’s earned Friendship all the praise and acclaim.

If Friendship has left you squirming in silence, there is a whole subgenre of black comedies that explore similar twisted dynamics. Here are 10 other cringeworthy black comedies that hit the same nerve as Friendship.

‘The Cable Guy’ (1996)

Matthew Broderick plays Steven Kovacs in The Cable Guy. He is a recently single architect who moves into a new apartment and bribes his cable installer, Jim Carrey’s Chip Douglas, for free premium channels. It’s a harmless transaction, but it turns into a bizarre and disturbing friendship where Chip latches onto Steven with obsessive intensity. He installs a home theater system, throws a chaotic party, and even hires a sex worker to seduce Steven, all in the name of friendship.

Toxic Masculinity and Loneliness

Ben Stiller’s direction is so iconic that it makes use of the discomfort of Steven trying to cut off Chip, and Chip only retaliates with escalating acts of sabotage. Carrey’s manic energy stretches into something darker than his usual slapstick and the movie basically thrives on his pathological need for connection, making the laugh feel slightly wrong. Though critics were divided at release, The Cable Guy has since earned cult status for being so cringey it borders on horror.

‘Rushmore’ (1996)

Max Fischer is the most passionate and dedicated 15-year-old at the elite Rushmore Academy, where he excels at everything but academics. His life is a whirlwind of clubs, plays, and schemes. And his world turns upside down when he falls for Rosemary Cross, a first-grade teacher. Things get complicated for him when Max’s mentor, the witty and melancholic industrialist Herman Blume, also falls for Rosemary.

Character Study Laced with Awkward Humor

Wes Anderson broke out with Rushmore, and it’s easy to see why the delightfully offbeat film is still a worthy addition to his quirky catalog. It’s all about youthful ambition and unrequited love, but the comedy is dry, and the cringe is constant, making the emotional core sneak up to you when you least expect it. Jason Schwartzman’s Max is insufferably earnest, and Bill Murray’s Blume is the perfect contrast. Together, their dynamic is as unforgettable and uncomfortable as Craig and Austin’s in Friendship.

’50/50′ (2011)

In 50/50, Adam Lerner is a 27-year-old radio journalist who is diagnosed with a rare spinal cancer. His odds of survival are 50-50, and now he’s forced to navigate the emotional and physical challenges of his diagnosis and treatment, betrayal, and reluctant self-discovery. His best friend Kyle tries to inappropriately lighten the mood, while Adam’s girlfriend Rachael proves unreliable. Adam’s therapist, Katherine, still in training, becomes his emotional anchor.

Emotional Whiplash With a Wink

Directed by Jonathan Levine and based on writer Will Reiser’s real-life experience, 50/50 is a refreshingly honest movie that makes something as serious as terminal illness funny without being flippant. The cringe comes not from the diagnosis, but from the way people react to it. Awkwardly, silently, or with misguided good intentions. It earned Golden Globe nominations and a whole lot of praise for making discomfort a part of the healing.

‘What About Bob?’ (1991)

Directed by Frank Oz, What About Bob? centers on Bob Wiley, a neurotic, phobia-ridden man who clings to his therapists like his life depends on it. When his latest psychiatrist dumps him, he begins seeing Dr. Leo Marvin, a smug, self-help author who is about to go on vacation with his family. Bob, unable to cope with the distance, tracks Leo down to Lake Winnipesaukee and inserts himself into his life, charms his wife and kids, and becomes some sort of guru.

Therapy Leads to Total Meltdown

On one hand, Bob is thriving in the vacation setting. He’s overcoming fears and bonding with people. But Leo is spiraling into madness. Oz lets things simmer like this until it all boils over in spectacular fashion. Bill Murray’s Bob is lovable and insufferable at the same time, while Richard Dreyfuss plays Leo with the kind of exasperation that’s hard to match. The film was a box office success and has aged into a cult favorite, and is especially a must-watch for fans of Friendship.

‘Rap World’ (2024)

Set in 2009 suburban Pennsylvania, Rap World is a mockumentary that follows three friends, Matt, Casey, and Jason. They decide to record a rap album in one night, but their DIY music project quickly devolves into a mockumentary of stoned detours and failed romance. They procrastinate, argue, flirt, and fumble through the process and document their journey regardless.

A Generation That Thought It Was Cool

Directed by Conner O’Malley and Danny Scharar, Rap World is a lo-fi fever dream that puts the vibe of mid-2000s suburban youth culture in an hour-long capsule and offers it to us with great care. The comedy is rooted in delusion, misplaced confidence, and the kind of friendships that work because of how dysfunctional they are. The cast, including O’Malley, Jack Bensinger, and Eric Rahill, deliver raw performances, and every moment between them feels like a found-footage relic.

‘World’s Greatest Dad’ (2009)

Robin Williams stars in World’s Greatest Dad as Lance Clayton, a failed writer stuck teaching poetry at a high school where his son Kyle is a vulgar, sex-obsessed misfit. When Kyle dies in an autoerotic asphyxiation accident, Lance stages the scene to look like he took his own life. The fake note he adds to it goes viral, and suddenly Kyle is revered as a tortured genius. Lance takes the literary acclaim as a chance to double down as a fake journal writer.

Ugly, Honest, and Cathartic

Blending satire, grief, and moral collapse with genuine poignancy, World’s Greatest Dad is directed by Bobcat Goldthwait. Williams gives one of his most underrated performances of all time. It’s restrained, bitter, and devastating. The premise, which finds a father exploiting his son’s death for validation, probes the limits of morality and the human capacity for self-deception with a steady hand.

‘The Banshees of Inisherin’ (2022)

On a remote Irish island in 1923, Pádraic Súilleabháin is blindsided when his lifelong friend, Colm Doherty, ends their friendship and cites Pádraic’s dullness as the reason. The fallout is baffling and heartbreaking for him, and as Pádraic desperately tries to mend their fractured bond. But Colm, desperate to leave a legacy, threatens to sever a finger each time Pádraic talks to him. And he follows through.

Breakup Movie, or a Folk Tragedy?

The island’s eerie stillness and the backdrop of the Irish Civil War work in favor of director Martin McDonagh, whose wicked black comedy revels in the profoundly uncomfortable realities of long-term friendships. Colin Farrell and Brendan Gleeson deliver nuanced, lived-in performances, with Kerry Condon and Barry Keoghan adding layers of awkwardness and charm. The Banshees of Inisherin swept the awards season, earning nine Oscar nominations and winning multiple BAFTAs and Golden Globes.

‘Lars and the Real Girl’ (2007)

Lars and the Real Girl follows Lars Lindstrom, a painfully shy man living in a small Midwestern town. He’s emotionally stunted and terrified of human touch. One day, he announces that he is in a relationship with Bianca, who happens to be a life-sized sex doll. His brother Gus and his sister-in-law Karin are horrified, but with local doctor Dagmar guiding Lars, the entire town decides to play along so he can slowly open up to a real human connection.

Delusion and Healing

Craig Gillespie’s offbeat black comedy walks the tightrope between absurdity and emotional breakthrough. It never mocks Lars, but nudges him toward actual growth. Ryan Gosling is committed to playing Lars delicately, and the town’s collective buy-in to the delusion is both hilarious and moving. Lars and the Real Girl also has a rewarding payoff about grief, community, and the strange ways we cope.

‘In Bruges’ (2008)

Martin McDonagh’s feature directorial debut, In Bruges, begins with a botched hit in London, which accidentally kills a child and sends hitmen Ray and Ken to lay low in Bruges, Belgium. Ray hates the medieval city and Ken finds it peaceful. Their odd-couple dynamic is tested when their boss Harry, orders Ken to kill Ray as punishment for the child’s death. When Ken helps Ray escape instead, Harry shows up, and it leads to a bloody showdown.

A Purgatory of Sorts

A surreal film set and a tragic misunderstanding overshadow the movie, which blends Catholic guilt, absurd violence, and philosophical musings with pitch-black humor. It goes without saying that Colin Farrell and Brendan Gleeson’s chemistry holds the movie together, with one a mess of remorse and the other bringing warmth. The cringe is constant, but it’s all in service of a deeper emotional reckoning.

‘I Love You, Man’ (2009)

Paul Rudd and Jason Segel star in I Love You, Man. Rudd plays Peter Klaven, a successful real estate agent who has just gotten engaged to Zooey, but he has no close male friends, which means he has nobody to show up as his best man at the wedding. Peter goes on “man-dates” and finds Segel’s Sydney Fife, a laid-back investor with a penchant for oversharing. When their bromance deepens, Sydney’s influence starts to strain Peter’s relationship and career.

Platonic Male Bonding and Boundaries

If Friendship made you laugh and then feel horrible about laughing a minute later, then John Hamburg’s I Love You, Man leans into a similar kind of weirdness found in adult male friendships. Rudd and Segel have impeccable comedic timing and their chemistry is the soul of some of the movie’s most uproariously funny scenes that mine rich veins of cringeworthy humor from Peter’s earnestness and Sydney’s lack of filter.