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Funniest Novels of All Time

April 16, 2011 18 comments

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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