The best humor books from more than a century ago that remain funny today

Hold on! Anton Chekhov? Not that giant of Russian literature who gave us some of the most poignant, brooding, melancholy views of family life in dramatic works like The Seagull and The Cherry Orchard? Probably the biggest surprise on this list, Anton Chekhov wrote comedy for years and as a young adult supported his family by writing humorous sketches about Russian life for the magazine Oskolki. While most famous for his plays, Chekhov was an incredibly gifted short story and humor writer. In one of his tightest yarns, “An Avenger,” confused young Fyodor Sigaev goes shopping for an appropriate revolver to mete out justice after he discovers his spouse cheating on him. But once at the shop, the sheer number of firearm choices he’s presented with quickly overwhelm him. 

“. . . I would advise you, M'sieur, to take this superb revolver, the Smith and Wesson pattern, the last word in the science of firearms. We sell a dozen every day for burglars, wolves, and lovers.”

Before Monty Python, Fawlty Towers, Black Adder, and Douglas Adams, there was Jerome K. Jerome and Three Men in a Boat. While probably the least familiar name on this list, 3MB holds up astonishingly well today. Initially, the book was intended to be a travel guide, but the humorous elements of the narrative took hold and wouldn’t let go. The story takes the simple premise of three highly civilized British friends deciding to weather all the myriad discomforts of a simple camping trip. Despite predating all the modern greats of British comedy, 3MB has a very similar tone to those more recent works and inspired many of those authors. And if you like Three Men in a Boat, you’re in luck. Jerome wrote a sequel: Three Men on the Bummel.

“I objected to the sea trip strongly. You start on Monday with the idea implanted in your bosom that you are going to enjoy yourself. You swagger about the deck as if you were Captain Cook. On Tuesday, you wish you hadn't come. On Wednesday, Thursday, and Friday, you wish you were dead. On Sunday, you begin to walk about again, and take solid food. And on Monday morning, as you stand by the gunwale, waiting to step ashore, you begin to thoroughly like it.”

To be honest, Mark Twain almost didn’t make this list. Despite being considered America’s greatest satirical author (and some might say the greatest author, period), as well as ostensibly the father of stand-up comedy (Twain was touring around doing live monologue shows a century before anyone coined the term “stand-up”) I had a hard time finding any of his pieces that actually made me laugh out loud. Yes, The Celebrated Jumping Frog of Calaveras County is well-written and was likely hysterical in its day. But I had to dig deep to find something both timeless and gut-splitting.

I found both in Roughing It, Twain’s semi-autobiographical travel memoir. In this book written between 1870-1871, Twain reflects on his adventures across the U.S. from Missouri to Hawaii. The anecdotes are consistently great, funny, and observational, none more so than the perfect “Story of the Old Ram” – the grandaddy of all shaggy dog stories. Twain recounts ole Jim Blaine’s long meandering story of how his grandfather fetched an old ram from Illinois. We get a dozen different situations within this ramble. But what about the actual “old ram”? Well, you’ll just have to read the story to find out.

“Miss Jefferson had a glass eye and used to lend it to old Miss Wagner, that hadn't any, to receive company in; it warn't big enough, and when Miss Wagner warn't noticing, it would get twisted around in the socket, and look up, maybe, or out to one side, and every which way, while t' other one was looking as straight ahead as a spy-glass. Grown people didn't mind it, but it most always made the children cry, it was so sort of scary.” 

“A Trivial Comedy for Serious People.” It’s actually quite exciting to me how well Oscar Wilde’s comedy holds up today. Known as one of the greatest wits of his generation, Wilde was a master of many narrative forms including gothic horror (The Picture of Dorian Gray), and children’s literature (The Selfish Giant), but in Earnest, he creates one of the greatest comedy of manners ever put to paper. In this play, two young, roguish gentlemen conspire to effectively court the ladies of their interests. What makes the piece so timeless and relevant today, is the utter shamelessness of Wilde’s heroes. He has no qualms in portraying his leading characters as clever, charming and utterly willing to deceive all others to get what they want. If you’ve never read Wilde, go pick up The Importance of Being Earnest right now. OMG, what are you waiting for?!  

Algernon: Besides, your name isn't Jack at all; it is Ernest. 

Jack: It isn't Ernest; it's Jack. 

Algernon: You have always told me it was Ernest. I have introduced you to everyone as Ernest. You answer to the name of Ernest. You look as if your name was Ernest. You are the most earnest-looking person I ever saw in my life. It is perfectly absurd your saying that your name isn't Ernest. It's on your cards. Here is one of them. 'Mr. Ernest Worthing, B. 4, The Albany.' I'll keep this as a proof that your name is Ernest if ever you attempt to deny it to me, or to Gwendolen, or to anyone else.”

Before sitcoms, stand-up, SNL, and absolutely any great comedy movie you can name – there was Gilbert & Sullivan. Okay, yes they wrote operas (“light operas” technically; really more like our musicals today), but these works were created to be popular, scandalous, funny, and with hummable tunes for the masses. G&S operas were absurd, fantastic, politically incorrect, hysterical, “topsy turvy” extravaganzas that satirized (much like Wilde) the bourgeois mores of the day. Astonishingly, most of it holds up today, which is why you can still see Gilbert and Sullivan's productions being perpetually staged across the globe. If you can see one of their productions live – or on YouTube – go for it. But the libretto’s themselves are highly readable and funny. The Pirates of Penzance is a good gateway to their other works. It’s full of sex, crime, cops, pirates, bathing beauties, and non-stop earworms; and includes two of the funniest songs in musical theatre history: “A Paradox”, and “The Modern Major-General Song”.

From “A Paradox: “You are the victim of this clumsy arrangement, having been born in leap-year, on the twenty-ninth of February; And so, by a simple arithmetical process, you’ll easily discover, that though you’ve lived twenty-one years, yet, if we go by birthdays, you’re only five,
and a little bit over!”