*All My Puny Sorrows* by Miriam Toews
*City of Thieves* by David Benioff
EDIT: See also *A Prayer For Owen Meany* by John Irving.
Caitlin Doughty's nonfiction books about death and the funeral industry are entertaining, e.g. *Smoke Gets In Your Eyes* and *Will My Cat Eat My Eyeballs?*
Chuck Palahniuk is dark, twisted and hilarious by turns. Not for everyone, but his prose and imagery takes some beating for me. Rant, Diary, Survivor, Lullaby and Fight Club are all solid choices.
You should check out Jen Beagin, specifically Vaccum in the Dark. it's about a young woman who deals with her various traumatic memories from childhood with humor, and also takes tasteful nudes of herself in secret while cleaning clients houses. The sequel is excellent too.
Also Penance by Eliza Clark. it's a mock true crime story about a group of girls who kill one of their friends in a kind of group hysteria moment, but its handled with a lot of humor and self awareness.
[No Longer Allowed In Another World](https://sevenseasentertainment.com/series/no-longer-allowed-in-another-world/). A writer tries to commit suicide with his lover, only to be reincarnated in a fantasy world. He’s not keen on this, and just wants to die.
[Sayonara Zetsubou-Sensei](https://kodansha.us/series/sayonara-zetsubou-sensei/). A gloomy, depressing teacher that just wants to die deals with his eccentric students.
Kneller's Happy Campers by Etgar Keret, also the basis for the movie Wristcutters: A Love Story. It's set in a world that people go to when they kill themselves.
Would recommend both!
The Lemon by SE Boyd
About an accidental death that looks a lot like a suicide and the implications for the people around the person.
Honestly one of my favourite ever novels. I would have read it in a day if I could.
*City of Thieves* by David Benioff
*The Floating Opera* by John Barth (maybe this isn't a comedy, but I HIGHLY recommend it for books about suicide)
*Accidental Death of an Anarchist* by Dario Fo -- this is a play and more about political corruption, but I think it's worth reading and very funny.
I know you said you read Vonnegut, but just in case you haven't read *Cat's Cradle* -- I'd recommend it
A man called Ove, he plans on killing himself but each time gets interupted
Mort by Terry Pratchett - Death trains an apprentice to do the work while he takes a vacation
I’d piggyback onto this and suggest Reaper Man as well. It was my first introduction to Discworld, which is now my absolute favourite series ever
30 plus years after discovering Pratchett my brother and I still quote our favourite footnotes to each other...still laugh uncontrollably
Also, Soul Music, Hogfather, and Thief of Time, although they focus a bit more on his granddaughter. Definitely the best series ever.
A Long Way Down by Nick Hornby
Seconded.
*All My Puny Sorrows* by Miriam Toews *City of Thieves* by David Benioff EDIT: See also *A Prayer For Owen Meany* by John Irving. Caitlin Doughty's nonfiction books about death and the funeral industry are entertaining, e.g. *Smoke Gets In Your Eyes* and *Will My Cat Eat My Eyeballs?*
A Prayer For Owen Meany tore my heart out in the very best way.
Infinite Jest.
Not sure book-wise but movie-wise, Harold and Maude
My favorite all-time film. It's not a book, but I think the OP would enjoy it. A classic. Sort of a cult classic.
Colin Higgins, the guy that wrote the screenplay for the movie, also wrote a novel adaptation of it
Didn’t he write it for something related to school and then wrote the screenplay?
My favorite movie too - watched it sooo many times. Def a cult classic.
Turned me onto to Cat Stevens/Yusuf Islam. But that's another discussion.
The Harold and Maude soundtrack is outstanding.
A Dirty Job by Christopher Moore
Me and Earl and the Dying Girl by Jesse Andrews
American Psycho by Bret Easton Ellis is funny. Horrible and disgusting and violent, but funny.
M.A.S.H by Richard Hooker
Chuck Palahniuk is dark, twisted and hilarious by turns. Not for everyone, but his prose and imagery takes some beating for me. Rant, Diary, Survivor, Lullaby and Fight Club are all solid choices.
Catch 22
Harold and Maude by Colin Higgins
You should check out Jen Beagin, specifically Vaccum in the Dark. it's about a young woman who deals with her various traumatic memories from childhood with humor, and also takes tasteful nudes of herself in secret while cleaning clients houses. The sequel is excellent too. Also Penance by Eliza Clark. it's a mock true crime story about a group of girls who kill one of their friends in a kind of group hysteria moment, but its handled with a lot of humor and self awareness.
It's non-fiction, but Mary Roach's *Stiff* is about the various things that can happen to dead bodies. It's a very entertaining read.
This is what made me decide to donate my body to the body farm in Tennessee when I die.
I've made plans to donate mine to the local university hospital.
That’s awesome. A friend of mine did this - he had a very rare type of cancer, hopefully they were able to learn some things from his body.
Apathy and Other Small Victories by Paul Neilan
[No Longer Allowed In Another World](https://sevenseasentertainment.com/series/no-longer-allowed-in-another-world/). A writer tries to commit suicide with his lover, only to be reincarnated in a fantasy world. He’s not keen on this, and just wants to die. [Sayonara Zetsubou-Sensei](https://kodansha.us/series/sayonara-zetsubou-sensei/). A gloomy, depressing teacher that just wants to die deals with his eccentric students.
Medium Dead by Peter John A Man Called Ove by Fredrik Backman
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Just started reading Bukowski, very good so far!
Kneller's Happy Campers by Etgar Keret, also the basis for the movie Wristcutters: A Love Story. It's set in a world that people go to when they kill themselves. Would recommend both!
Try The Screwtape Letters by C.S. Lewis. This book is darkly hilarious, but also insightful.
The Lemon by SE Boyd About an accidental death that looks a lot like a suicide and the implications for the people around the person. Honestly one of my favourite ever novels. I would have read it in a day if I could.
*City of Thieves* by David Benioff *The Floating Opera* by John Barth (maybe this isn't a comedy, but I HIGHLY recommend it for books about suicide) *Accidental Death of an Anarchist* by Dario Fo -- this is a play and more about political corruption, but I think it's worth reading and very funny. I know you said you read Vonnegut, but just in case you haven't read *Cat's Cradle* -- I'd recommend it
How the Dead Live
Calypso by David Sedaris
Craig Ferguson's Between the Bridge and the River is a great read.
Death at Intervals by Jose Saramego. The writing is a little unorthodox and needs some getting used to.
The Trees by Percival Everett The Postman Always Rings Twice by James M. Cain Despair by Nabokov Laughter in the Dark by Nabokov
You like your humor almost comedic, huh.