20 Dark & Hilarious Books Like My Year of Rest and Relaxation

Ottessa Moshfegh has stormed to the front of literary fiction recently, publishing a plethora of books that have received numerous awards, fantastic ratings, and brilliant critical reviews. Her books often make it to the top of reading recommendation lists and her unique writing style has engrossed fans across the globe.

Moshfegh adopts an interesting narrative tone, one that delves deep into her character’s psyche and unleashes their extreme inner thoughts, desires, and fears, no matter how ugly or unfiltered. 

Many critics have reviewed her work as a breath of fresh air – she details mental health, female desires, sex, and social interaction in such a raw and arguably crude way, expressing emotion and inner dialogue in one of the most realistic forms seen in literature.

My Year of Rest and Relaxation tells of a privileged white woman who is fed up with life. She visits a therapist and has a complex relationship with her parents and her mental health gets to such a dire stage that she decides to take a whole year off and try to sleep throughout it all. 

This involves taking a multitude of different prescription pills to try and help her shut off, reduce her symptoms of anxiety and isolate herself from the rest of the world.

During the story, she experiences the breakdown of friendships, numerous complicated sexual and romantic relationships, grief, loss, and the effects of taking large amounts of medicated drugs for an extended period of time. All of these events are detailed with such precision and told through the protagonist’s frank, honest, and often crude inner dialogue. 

My Year of Rest and Relaxation is a fantastically funny, raw, and dark story that follows complex themes and narrates the ‘thoughts you wish you didn’t have’, which almost everyone will be able to relate to. 

If this book sounds like something you may enjoy, go ahead and read it! Its reviews are brilliant and it is well-deserving of its success despite the weird and often uncomfortable narration. 

This article will take you through 20 similar books that are both complex and funny, honest and surreal, and always enjoyable. 

Convenience Store Woman by Sayaka Murata

This novel tells the raw story of Keiko Furukura, a 36-year-old woman living in Tokyo. She has always been somewhat of a social outcast but learns more about people, society, and interaction when she takes a job in a local convenience store. 

Convenience Store Woman delves into the mind of an unusual woman trying to act normal based on what she observes and with the growing pressure of finding a husband, tries to navigate the dating scene. 

The New Me by Halle Butler

Millie is 30 years old and feeling the pressure to get her chaotic life back on track. She has so much going on and her life seems to run away with her and she feels out of control. So, she spends her evenings deciding how she will change. 

She makes plans to change her appearance, her job, and her mindset in order to find stability and calmness. When the offer of a permanent, well-paid job comes about, everything Millie’s been planning for seems to be within reach. But is it what she wants? Or does the idea of a ‘perfect’ life seem mundane to her now? The New Me will be relatable for many readers and offers hilarious insight into the mind of a woman faced with relationship pressure, job pressure, and financial pressure.

Heaven by Mieko Kawakami

From one of the most highly-praised Japanese novelists of the modern generation, Heaven is a tender and honest portrayal of adolescence. Following a bullied high-school student, this novel offers a compelling insight into the mind of a suffering teen, who creates a deep connection with a classmate that faces similar treatment. 

Heaven explores the beauty that can be unearthed in mutual pain and while detailing the impacts of mistreatment on a developing mind in such intricate detail, Kawakami also creates a beautiful relationship that’ll have you reaching for the tissues and help you gain perspective.

Eleanor Oliphant is Completely Fine by Gail Honeyman

Eleanor Oliphant is Completely Fine unsurprisingly follows Eleanor, who struggles socially. She’s unfiltered, sometimes rude, and as a result, a total loner. But when she meets Raymond, an awkward, energetic, smelly colleague, her life turns upside down. 

Their paths cross while helping a vulnerable elderly man on the sidewalk. These three very different characters have one thing in common – they all lead isolated lives. So, while uncovering the mental infringements that come with feeling alone, Honeyman orchestrates a quirky but beautiful relationship that will provide the reader with comfort and a lot of laughs.

The Remains of the Day by Kazuo Ishiguro

Blending the complex themes and humor (that can be found in most books on this list) with an intriguing historical setting, Ishiguro creates one of the most insightful stories in his collection. 

The Remains of the Day follows Stevens, a butler serving at Darlington Hall in the aftermath of World War II England. As his retirement looms, he takes some time to reflect on his service and the great philanthropic man he served. 

This journey through memory encapsulates strong emotions and core events that help him to uncover the truth about his master. This book is brilliantly character-driven and dives headfirst into the mind and memory of a servant. 

All’s Well by Mona Awad

Mona Awad’s reputation for dark humor is mostly driven by her publication Bunny, which received several awards and is praised for its hilarious and twisted plot lines. 

But All’s Well is an equally brilliant novel that is not as widely read. It concentrates on a failed actress, Miranda Fitch, who suffered an accident during a role that left her with a back injury. Now, she teaches theater at college level and is a little too close to losing her job.

This, combined with her marital disaster and reliance on painkillers is enough to tip anyone over the edge. But there’s one thing that can help Miranda get her career back on track. She is directing Shakespeare’s All’s Well That Ends Well, which could either save her job or plunge her into utter despair. This novel will make you laugh out loud at the expense of Miranda’s failing life – a truly relatable and exhilarating book.

Luster by Raven Leilani

If you enjoyed the raw, graphic depictions of desire, sex, and relationships in My Year of Rest and Relaxation, then this one’s for you. 

Luster follows Edie, a young woman who flirts and sleeps her way to unemployment. She is financially unstable, unqualified, and now, evicted. She has nowhere to go except seek help from her current boyfriend, the older and married Eric. 

With nowhere to go and no prospects, Edie is forced to move into Eric’s family home, which creates an unbelievably awkward dynamic. Edie’s situation as the young mistress, combined with the increasingly obvious racial disparities creates a brilliantly insightful story of a young Black girl trying to make her way in a white-dominated world.

Queenie by Candice Carty-Williams

This is another racially charged novel that provides a fantastically raw perspective, narrated by a 25-year-old Jamaican British woman living in London. She is racially torn, lacking any sense of belonging.

Queenie makes a variety of questionable decisions, covering everything from jobs to romantic relationships, and her brutally frank internal dialogue provides both humor and a refreshingly intense view of the world from a mixed-race perspective.

Everyone In This Room Will Someday Be Dead by Emily R. Austin

When death-obsessed, atheist and lesbian, Gilda, accidentally gets a job at a local Catholic church, things aren’t promising. Gilda is forced to hide her beliefs and sexuality from her new colleagues and attempts to fulfill the job requirements as best she can with limited Catholic knowledge or interest.

But when she starts a thread of emails with the best friend of her dead predecessor Grace, Gilda’s fascination with death reaches its peak. She can’t break the news of Grace’s death to her friend and so pretends to be her while she figures out how to navigate the situation. But Grace’s death soon becomes suspicious and the person impersonating her looks like suspect number 1. 

Everyone In This Room Will Someday Be Dead is a brilliantly funny novel that follows the kind-hearted protagonist as she gets herself into all sorts of awkward situations. With the dark theme of death tied to the hilarious narration, this novel is a must-read for any dark humor lover.

When You Read This by Mary Adkins

After his colleague tragically passed away at the age of 33 following a terminal illness, Smith finds a blog that Iris created while she was dying, which incorporates funny anecdotes, life lessons, and a devastating but brilliant new perspective. 

When You Read This follows Smith as he tries to publish Iris’s work, her last wish before she passed. But in order to do so, he’ll need the help of Iris’s grief-stricken sister. 

Sorrow and Bliss by Meg Mason

Martha’s life was perfect. She had a brilliant career and a romantic life in Paris, and now, she lives in rainy Oxford surrounded by highly qualified and successful mothers, in happy families, and living the ultimate suburban lifestyle. 

Martha struggles mentally, so she finds it difficult to socialize, let alone get a boyfriend. She doesn’t understand what’s wrong with her and isolates herself from pretty much everyone. Sorrow and Bliss is an honest and realistic depiction of the lives of those who don’t have it all. Told through an entertaining, sarcastic narrative, this novel explores some deep concepts and complex themes, guaranteed to have you laughing out loud and keep you thinking.

Severance by Ling Ma

This is a fantastically satirical novel that flirts with fantasy, apocalyptic themes, and real-life struggles. Severance follows Candace, a routine-obsessed millennial, suffering the loss of her parents, and navigating life in Manhattan as a Chinese immigrant.

So when an almost biblical plague takes over New York, Candace’s life is forced to change. It’s a story of secrecy, survival, and mental strain. Fantastically humorous and satirical, this book will keep you entertained despite the quirky premise.

Evvie Drake Starts Over by Linda Holmes

Evvie is recently widowed and suffers from the mental implications of losing her husband. She keeps herself confined and doesn’t want to believe her reality. 

Then her path crosses with Dean, a sports superstar who is miserable and losing his talent. A friendship blossoms between them both, reliant on one factor – they don’t ask each other about the other’s problems. But when friendship develops into something more, will they be able to keep secrets?

Evvie Drake Starts Over is a funny, heart-warming story that tackles dark and emotive themes like grief and failure.

Boy Parts by Eliza Clark

Living a life dominated by drugs, alcohol, sex, and cinema, Irina jumps at the offer to exhibit her art in a London gallery – her work predominantly centers around nude photos of male models.

Boy Parts delves into Irina’s psyche, offering a valuable and insightful perspective, and follows Irina’s career and relationship as she navigates the start of a new life. 

Elieen by Ottessa Moshfegh

Eileen was written by the same author, so you’re guaranteed something with a similar style here. This novel follows Eileen Dunlop, a lonely woman who was dragged into a crime when she worked in a prison in the 1960s. 

Now, she tells the story of how she disappeared and why. Eileen goes into depth about desperation, scandal, familial relationships, and mental health, all while using a dry and humorous narrative to create a complex and satirical tone.

Swimming With Bridgeport Girls by Anthony Tambakis

Ray has seen better days. He’s been sacked from his job with ESPN after publicly humiliating himself, he’s wanted by the New York police department, and his ex is happily engaged.

But when he receives inheritance money from a father he never knew, he makes every attempt to get his life back on track. Swimming With Bridgeport Girls is a witty, engaging, and relatable story of loss, failure, and struggle.

Cheat Day by Liv Stratman

David and Kit are happily married and have had a healthy relationship since college. But now they seem to be veering off in different directions. David is successful, earning heaps of money, and traveling with work, while Kit is in and out of unsatisfying jobs searching for purpose.

She is determined to pull herself together, which she believes starts with losing weight. Hungry and desperate for a sugar hit, she stumbles into a bakery, where she meets Matt, the man that would soon become her lover.

Cheat Day is a clever, funny, and heart-wrenching story of relationship struggle, failure, and indulgence.

Conversations With Friends by Sally Rooney

From the author who wrote the hugely successful novel Normal People, is Rooney’s debut, Conversations With Friends.

It follows the thoughts, desires, and experiences of two friends who get entangled in another marriage. Filled with complicated affairs, driven by desire, and leaving a thought-provoking message, this novel is not one to miss.

The Bell Jar by Sylvia Plath

This is one of the rawest and most famous novels that portray the reality of living with mental health. Told by one of the most innovative authors who suffered mentally herself, Plath constructs a tragic and beautifully written story that follows Esther as she battles with mental health, medication, and loss. 

The Bell Jar is not for the readers seeking a funny read but it will provide fantastic insight into the mindsets of those struggling and uses such intricate narration that you’ll lose sight of where reality stops and insanity begins.

The Idiot by Elif Batuman

This innovative novel is constructed through a web of relationships, made accessible through the new world of email. Set in 1995, The Idiot follows Selin, who navigates Harvard as the daughter of Turkish immigrants. 

She befriends a Serbian girl, Svetlana, and soon connects with Hungarian mathematician Ivan. That summer, Selin travels Europe with Svetlana, experiencing relationships, thrills, and adventure along the way. 

Final Thoughts

This collection of dark comedies will have you laughing out loud and get you asking questions. Most of these books contain extremely raw narratives, detailing intimate experiences and thoughts that could be a little too graphic or honest for some readers. They all follow interesting concepts, are character-driven, show a keen interest in the human psyche, and are extremely thought-provoking.

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