The OP doesn’t actually specify a timeframe, which I assume is intentional, so:
It’s a few decades since I read it, but I remember laughing so hard that I was completely debilitated: Puckoon by Spike Milligan.
And without wanting to sound utterly pretentious, The Life And Opinions Of Tristram Shandy, Gentleman by Laurence Sterne is (at times) howlingly funny, as well as being (at times) inexplicable; and (fascinatingly) a couple of centuries ahead of its time.
My favorite is PG Wodehouse’s “Mating Season,” one of the Jeeves novels. My favorite Moore is “Bite Me,” my favorite Adams is “Dirk Gently’s Holistic Detective Agency.”
I generally don’t like funny novels, nothing against comedic writing but there is something about the intersection between the long form novel and comedy that doesn’t mesh with me.
That said, when I was a teenager I loved Dalmiro Saenz’ novel “Yo tambien fui un espermatozoide” (I was an spermatoza too), which begins
“Writing a book on yourself is a bit uncomfortable, I usually prefer writing on a desk”
Carl Hiassen’s books are generally very funny. His stories invariably take place in Florida, a place where I think he only lives so he can write about the idiotic things Floridians do.
I remember laughing like a loon when I read Auntie Mame (Dennis) a hundred years ago.
I’m surprised that neither the NY Times article, nor anyone in the thread (that I saw, anyway) mentioned Kurt Vonnegut. I’ve read many of his books and he never fails to keep me laughing, despite the often bleak subject matter.
Excellent choice, but Douglas Adams was better for me. I had read pretty much every Vonnegut and loved many of them. Cat’s Cradle would be my top pick for him for funny.
Cat’s Cradle, yes. Some of Vonnegut’s novels, though—maybe most of them—really don’t have a lot of material that seems to be played for laughs (Mother Night in particular comes to mind).
But there’s plenty of absurdity to be found throughout his work, and on the basis of just using his imagination, he accounts for himself very well.
I appreciate and admire your taste in books, since it overlaps a lot with my own. Minor quibble on your Stephenson choice, as I prefer the earlier novels where they benefit from having an editor to cut down the meandering, but I have on occasions read the part of the intro about “stupendous badass” and the later section about the giga-molars outloud to friends who ended up LOLing and on occasion, doing so with tears in their eyes. Still, I’d have mentioend Zodiac or Snow Crash first.
And you’re 100% right about differentiating between early and late Christopher Moore if you want to load on the funny - I’m not saying later Moore is bad and I have a copy of Lamb (@carlb’s suggestion) but the later stuff IMHO is more clever but less LOL.
A good question though is brought up by Cal Meacham:
Because direct and style parodies are hugely amusing to me. Or ones that invert and send up genre tropes. While the level of writing is often not enough to meet the standards of the authors mentioned in-thread, I love the books Illegal Aliens and Villians by Neccessity.
Believe it or not, the works of Mark Twain. Generally not all the way through. But parts of A Connecticut Yankee in King Arthur’s Court are great. So sare parts of Life on the Mississippi and The Innocents Abroad, although those aren’t novels.
The James Herriot books are hilarious, in parts. Other parts are very sad, so I wouldn’t call them comedic novels, but the funny stuff is very good. Tristan always slays me.
A few people have mentioned funny fantasy novels. If you like that genre, check out the Tales of Pell series by Delilah Dawson and Kevin Hearne; Kill the Farm Boy, No Country for Old Gnomes and The Princess Beard.
A fellow fan I see, but I got there first! (unreasonable smugness satisfied)
Oh, and I came back to the thread after a DUH moment, but in terms of loving style homages, I’d have been remiss to not mention The Princess Bride novel, although it’s overshadowed in many ways by the amazing film version.
And for fans of amusing fantasy, I always suggest the writings of Steven Brust, especially the various novels of the Jhereg/Vlad Talos/Dragaera series.
The novel is far funnier than the movie. It’s written in the first person as Lorelei Lee’s diary, and she tries to conceal a lot about herself and unintentionally reveals a lot, which reminds me a bit of Thackeray’s Barry Lyndon. Anita Loos was a master of funny, crackly dialogue, which is why Jean Harlow liked to have Loos on staff to write lines for her. I re-read it every once in awhile to laugh all over again.