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Funniest Novels of All Time

Every now and then I type “funniest novel” or “funniest writer” or something into a search engine to see if I can find any ideas for what to read next. And I’m always shocked at how much stuff comes up that isn’t funny at all. Or, often, there’ll be some things that are sorta funny, but not primarily funny. Like Neal Stephenson. Stephenson’s great, and he does clearly have a sense of humour, and he uses it in his writing, but he’s not writing comedies. So if (say) Snow Crash is on your list of the funniest books you’ve ever read, well… you haven’t read that many funny books.

So here are mine, anyway (fiction only, roughly in order), in case someone else out there is doing the same kind of thing that I did. Hope the list helps; if nothing else I can promise that these books are supposed to be funny. (I’m more interested in bringing attention to things I like than in arguing that my list is actually definitive.) I’ll group the entries by author so that it’s not just a list of Wodehouse novels.

(There are some frequently cited books that I don’t have on here. I’ve seen lists that rank Kingsley Amis’s Lucky Jim highly, for instance. I read Lucky Jim about ten years ago and I remember liking it okay but I don’t think I got any good yoks from it. And then there’s John Kennedy Toole’s A Confederacy of Dunces, which I couldn’t stand.)

19. Greg Costikyan: Another Day, Another Dungeon. First book in a planned fantasy trilogy that makes fun of Dungeons-and-Dragons-style adventuring. Lots of nice touches in it. Costikyan wrote the second book; it was okay. There probably won’t be a third.

18. Chris Moore: My favourite part of Chris Moore’s collected works is the scene in Island of the Sequined Love Nun where Tucker is pleading with the FBI guy. Sometimes I take the book down off the shelf just to read that one page.

17. W.E. Bowman: The Ascent of Rum Doodle. Parody of, what shall we call it, expedition writing.

16. Connie Willis: More of a science fiction writer than a comedy writer, but her To Say Nothing of the Dog is clearly meant to be funny from start to finish, and Bellwether is kind of similar.

15. Larry Doyle: I Love You, Beth Cooper. One of those last-night-of-high-school stories, but the key thing here is that Doyle doesn’t seem to have any limit on how outrageous he’s going to let things get.

14. Douglas Adams: Sure, The Hitchhiker’s Guide to the Galaxy is famous and funny, and I like it too, and the first three sequels, but it was Dirk Gently’s Holistic Detective Agency that really impressed me; fits together like a Swiss watch. The sequel doesn’t work quite as well but is still worth a look.

13. Lisa Lutz: The Spellman Files and its sequels. Tales of a quasifunctional family of compulsive private detectives. Great stuff. Only problem with these is that the comedy/mystery ratio skews so heavily to the comedy side.

12. Terry Pratchett: Pratchett is a fantasy writer who uses humour a lot. It doesn’t always work, but a) he’s a good fantasy writer, and b) he keeps the jokes coming, so they don’t all have to be winners for the books to be a success. Mostly I’m talking about the Discworld series, but he’s got other worthwhile books too.

11. Sherwood Kiraly: California Rush. Kiraly’s written four novels and seems to have stopped there, which is a shame. They’re all good, but his first one is his funniest. It’s a baseball novel about (this is my take) just what it would take to make a stadium full of fans go completely berserk.

10. Roy Blount, Jr.: First Hubby. Blount is one of my favourite writers. He’s written all kinds of humour stuff, but this is his only attempt at fiction. One of the things I like about it is that he sets up this one joke, a pun, so far ahead of time that you’d never know that that was what he was doing, and the pun is a good one but obviously not worth all the effort. I admire that.

9. O. Henry: He did write one novel, which I couldn’t get into; he’s most famous for his short stories, which are, as they say on Primer, handstakingly hilaripus. I don’t mean they were funny back when he wrote them and we can still smile politely at them now; I mean they’re still really funny.

8. Stella Gibbons: Cold Comfort Farm. This one works better if you’re familiar with the books it’s making fun of, D.H. Lawrence and stuff like that. I’m not very familiar with them, but I used my imagination and got by okay, so you shouldn’t have a problem either. Plus, Flora is one of the great characters of all time; never gives an inch of ground to anybody.

7. Anita Loos: Gentlemen Prefer Blondes (and, if you want, its sequel, But Gentlemen Marry Brunettes). A classic.

6. Saki: It took me forever to start reading Saki. I don’t know why. You’d think somebody would have recommended him to me. Anyway, he’s about like P.G. Wodehouse (see below) in a lot of ways, but with more of a mean streak.

5. Joe Keenan: Blue Heaven, Putting on the Ritz, and Lucky Star. Modern farces, I guess you’d call them. A top songwriting team gets mixed up in all kinds of confusion, intrigue, and deception; hilarity really does ensue.

4. Jean Shepherd: In God We Trust, All Others Pay Cash; A Fistful of Fig Newtons, for a start. You know the movie The Christmas Story? Based on Jean Shepherd’s books, which I guess aren’t completely fictional, but they can’t be all true, either. Despite Shepherd’s affection for the past, this is not nostalgia; it’s got too much of an edge on it for that.

3. Donald E. Westlake: Westlake is most famous for his “comic crime” novels, which are basically caper novels. In particular he had a series of books about ill-starred criminal mastermind John Dortmunder, who is basically about halfway between Professor Moriarty and Eeyore. Those are very good, and so is his other stuff (some of it funny and some more serious), but my favourite is his story Dancing Aztecs, about the frantic hunt for a valuable statue in 1970s New York.

(3b. Jay Cronley: Quick Change. Could totally be a Dortmunder novel.)

2. Dennis Hensley: He’s written two novels, Adventures in the (213) and Screening Party (which isn’t exactly a novel, although the aspects of it that are novel-like are what makes it so likable). Adventures in the (213), about wacky Hollywood hijinks, was pretty good. Screening Party, about a group of friends who get together to snark on movies, had me laughing so hard I couldn’t breathe more than once. Which basically never happens.

1. P.G. Wodehouse: I hope it’s not controversial to name Wodehouse as the funniest writer in the history of the English language. Not everything he wrote was great, but well over half of it was; some titles to look for are Right Ho, Jeeves, The Small Bachelor, Leave it to Psmith, and Barmy in Wonderland. There are lots, though.

I guarantee as soon as I post this I’ll think of three more books I should have included.

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  1. April 16, 2011 at 6:02 pm

    I know he’s on your list, but Terry Pratchett’s novel he wrote with Neil Gaiman Good Omens, is one of my favourite funny books (as opposed to funny-books!) of all time.

  2. April 16, 2011 at 7:13 pm

    I agree. Really, as funny books go, it’s pretty much just like a regular Pratchett book, isn’t it? It’s a lot easier to see Pratchett’s footprints on the book than Gaiman’s. (Also of note: Pratchett and Gaiman are individually responsible for the two most compelling personifications of Death in popular culture, but in the book where they team up, Death is actually not that interesting.)

  3. Kate
    April 18, 2011 at 8:24 pm

    So glad to see this list – I agree with so many (Chris Moore, Lisa Lutz, Terry Pratchett, Wodehouse) I’ll definitely check out those I haven’t read. I actually stumbled here looking for some (any) sympathy to my utter dislike of A Confederacy of Dunces…glad to find that too.

  4. April 18, 2011 at 8:51 pm

    Nice to hear; thanks. Let me know what you think of the ones you try, if you want.

    As for ACoD, all the people who like it must be able to find something worthwhile in it, but I honestly couldn’t tell you what.

  5. Carrie
    May 24, 2011 at 6:00 am

    Try Tim Moore’s ‘Frost on my Moustache’. Easily the funniest laugh out loud book ever written.

  6. May 24, 2011 at 8:58 am

    Yeah, that’s a good one. I was just doing novels, but there are a lot of funny travel books out there too. Moore, Bill Bryson, Will Ferguson… maybe I’ll do a list of those. You could even pile Gerald Durrell in there.

  7. Lionel
    July 19, 2011 at 4:06 am

    “The Poor Mouth” a memoir by Bonaparte O’Coonasa aka Myles na gCopaleen aka Flann O’Brien aka Brian O’Nolan. Any of O’Nolan’s stuff is gold, really.

  8. July 19, 2011 at 9:05 am

    Haven’t read that one. I did give At Swim-Two-Birds a try once and it pretty much just bounced off my forehead, but others may have better results.

  9. Jaime
    July 23, 2011 at 10:30 pm

    I’d add Twain and Jerome K. Jerome to your list and disagree with your take on Confederacy. Thanks for the list though!

  10. July 23, 2011 at 11:29 pm

    Twain is certainly funny but I think his nonfiction is funnier than his fiction, and I wasn’t listing nonfiction. I did enjoy Three Men in a Boat but probably not quite enough to make this list, and that’s the funniest thing of his that I’ve read.

  11. January 11, 2012 at 2:27 pm

    There’s a book called “Beauty to the Tenth Power! Or How I Got Screwed Over By A Dude, Got Cheap Cosmetic Surgery And Lived Happily Ever After” that’s funny, but it’s for women readers I think.

  12. January 11, 2012 at 3:11 pm

    That’s okay by me; I’ll give it a shot. Thanks.

  13. hankgillette
    August 23, 2013 at 11:10 pm

    It became the first of a series that rapidly declined in quality, but “Another Fine Myth” by Robert Asprin is the funniest fantasy novel I’ve ever read.

  14. August 24, 2013 at 10:46 am

    I’ve read the whole Myth series by Asprin many times, and at one time I did like it very much… but while I found the first book a fun read, I don’t recall laughing at it much. Maybe I should go back and give it another look.

  15. Tom
    September 15, 2013 at 12:00 am

    Hi. Just rad your “Funniest Novels” list (from 2011) and will read several of them. Thanks.

    I used to scour the library stacks for an hour or more looking for anything that could make me laugh that wasn’t non-fiction (which rarely does it for me). I wanted to share several laugh-out loud novels/authors that you might get some pleasure from:

    Carl Hiassen is tops on my list. His most recent stuff is not so great, but earlier writings (Sick Puppy, Stormy Weather in particular) were brilliant and had one of the great larger-than-life literary characters–an ex-governor of Florida known by many names, but generally goes by Skink. Wonderful, easy reads.

    Richard Russo’s Nobody’s Fool–Not laugh-out-loud hysterical, but damned amusing and solid writing writing by a Pulitzer Prize winner.

    I am with you on Wodehouse. Clever, clever, clever.

    You have probably read Chris Moore’s “Lamb,” but made no mention of it so I thought I would put it out there.

    There are also “The Fence Post Chronicles,” a series of books written by W.P. Kinsella. He wrote Field of Dreams (which I wasn’t crazy about), but this is a series of short story compilations written about the Erminskin Indian Rez in Canada are brilliant, funny, and often poignant. I have never met another soul who has read these (despite my best attempts to share the myrth), and they are well worth it. “Dance Me Outside”, “Moccasin Telegraph,” and “The Fence Post Chronicles” are three gems.

    Lastly, a birtish author names Anne Maxted’s first two books–“Getting Over It” and “Running in Heels”–very funny Brit humor and very readable.

    Enjoy,

    Tom

  16. September 15, 2013 at 11:29 am

    I like Hiaasen a lot, but to me he’s one of those writers who isn’t primarily funny; he’s funny while he’s doing other stuff. He’s got his gonzo crime/environmental stories that _also_ happen to be very funny. So I agree with you but still don’t feel that he belongs on this list. (My favourites of his are Native Tongue and Strip Tease.)

    I mentioned Moore, but not Lamb. Lamb is certainly one of his best. Have you read Sacre Bleu? Not as funny as he usually is, but maybe his best overall book anyway.

    I read Kinsella’s Fencepost Chronicles quite a while ago, and I remember liking them, but I don’t remember them as being that funny. Maybe I’ll have to go back and check ’em out again.

    And thanks for the Maxted and Russo recommendations; I’ll put ’em on my to-read list.

    • Tom
      September 15, 2013 at 4:58 pm

      I have not read Sacre Bleu and will check it out. Thanks.

      Re. the Kinsella Books: First off, nice to have finally met someone who has read them. I worked with the tribes here in Albuquerque for 5 1/2 years (mental health counseling) and took great pleasure in the amazing-yet-understated Navajo humor. It’s more “that” kind of humor. It made me laugh because I lived it and got it on a visceral level.

      The Hiassen books: yes, more off-and-on, with the humor woven in between the (as you put it) enviro-gonzo stuff, but they had a fair amount of laugh-out-loud moments for me. Loved Striptease. Not crazy about Native Tongue.

      I was talking about your blog comment to my wife today on a hike, and how I agreed that there were so few purely comic pieces out there. When i first started reading the Maxted novels, they struck me more as “Chick Flick” humor, but I quickly turned the corner into appreciating them for being a nice bit of writing.

      Anyway, thanks for the dialogue.

      Tom

  17. February 25, 2014 at 10:30 pm

    If anybody’s still checking in here for what people are saying about funny novels, I have a name to add: Patrick Dennis. All I’ve read of his so far is Auntie Mame, but it was pretty funny, and I’ve got Little Me in my to-read pile.

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