Hitchhikers guide 4 book trilogy, and the Dirk Gently books. All by Douglas Adams.
Have you read anything by Terry Pratchett? I just finished The Colour of Magic, the first book in the Discworld series. It reminded me quite a bit of Hitchhikers in its tone and style of comedy.
Have you read any Robert Rankin? His Brentford trilogy might be your cup of tea too.
Kurt Vonnegut - God Bless You, Mr. Rosewater
John Kennedy Toole - A Confederacy of Dunces
Carl Hiaasen - Tourist Season
Since I love the first 2 I'm trusting your taste and grabbing the 3rd
The Illuminatus! Trilogy by Robert Shea and Robert Anton Wilson. Imagine a world in which EVERY SINGLE conspiracy theory was true and where "The history of the world is the history of the warfare between secret societies".
Bill Bryson’s travel books, especially A Walk in the Woods and Down Under.
Terry Pratchett’s Discworld series. Like the whole thing. Can’t pick a favourite.
David Sedaris - Me Talk Pretty One Day
John Birmingham - He Died With a Felafel in his Hand
Terry Pratchett’s Discworld series. Like the whole thing. Can’t pick a favourite.
I would disagree with that. The last 3-4 books were... Not good. He was already showing signs of Alzheimers by then, and it was reflected in his writing. He died shortly after the final book, and, while it had flashes of his brilliance, it was clear that he was having a very hard time writing anything coherent by that time. Up to that point, he was fantastic. "Small Gods" is one of my favorite books about religion and belief, and he disguised it as comedic fantasy.
All Creatures Great and Small (and others in the series) by James Herriot.
Fifthing (can't second) Douglas Adams.
Especially love the Dirk Gently books. Seconding Bill Bryson.
In no particular order:
Donald E Westlake, Dortmunder series
Dave Barry, Big Trouble
*Janet Evanovich, One for the Money and etc.
Donna Andrews, Murder with Peacocks and etc.
Early Carl Hiassen
anything by Christopher Moore
Daisy Fay and the Miracle Man by Fannie Flagg
I haven't read that particular book, but I love Frannie Flagg.
Some candidates:
I don't know whether Finnegans Wake is funny (and I don't know whether I'll be able to know that after finishing it), but I certainly extract quite a bit of fun from reading it.
Almost everything by Terry Pratchett. Just beware the last few books, where he was clearly suffering from Alzheimers. "Good Omens" (with Neil Gaiman) is a fantastic starting point. In the laster books, Pratchett was using his fantasy setting to dissect current social problems, usually very effectively; the 'boot theory' comes directly from Pratchett.
Everything by Douglas Adams.
Charles Stross' "The Laundry Files" series; how bureaucrats deal with Lovecraftian horrors.
Glen Cook's "Garrett P.I." series. Not really comedy, but has a strong element of the ridiculous, and plays off of the tropes established by Dashiell Hammett and Raymond Chandler in a high fantasy setting.
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