1. Don Quixote by Miguel de Cervantes (1605, 1615). Considered literature’s first great novel, Don Quixote is the comic tale of a dream-driven nobleman whose devotion to medieval romances inspires him to go in quest of chivalric glory and the love of a lady who doesn’t know him. Famed for its hilarious antics with windmills and nags, Don Quixote offers timeless meditations on heroism, imagination, and the art of writing itself. Still, the heart of the book is the relationship between the deluded knight and his proverb-spewing squire, Sancho Panza. If their misadventures illuminate human folly, it is a folly redeemed by simple love, which makes Sancho stick by his mad master “no matter how many foolish things he does.”
2. Tristram Shandy by Laurence Sterne (1759–67). Sterne promises the “life and opinions” of his protagonist. Yet halfway through the fourth volume of nine, we are still in the first day of the hero’s life thanks to marvelous digressions and what the narrator calls “unforeseen stoppages” — detailing the quirky habits of his eccentric family members and their friends. This broken narrative is unified by Sterne’s comic touch, which shimmers in this thoroughly entertaining novel that harks back to Don Quixote and foreshadows Ulysses.
3. Joseph Andrews by Henry Fielding (1742). The comic trouble starts when a naive footman rejects the advances of his employer, Lady Booby, and her servant, Slipslop. Cast out, he and the saintly Parson Adams hit England’s rough roads in search of Joseph’s beloved, Fanny Goodwill. Like Don Quixote and Sancho Panza, the world rewards their goodness with violent complication. After Joseph finds Fanny — who might be his sister — Fielding amps up the sexually charged farce in this novel of friendship and virtue that satirizes Samuel Richardson’s novel Pamela.
4. Norwood by Charles Portis (1966). The comic conversation and surreal adventure that distinguish Portis’s fiction shine in this first novel about Norwood Pratt, a war hero with country music dreams who’s stuck in a small Texas town. Seeking escape, Norwood decides to find an old Marine buddy who owes him seventy dollars. His trip to Manhattan and then Memphis is filled with quirky characters (a midget, an educated chicken), strange situations, and homespun wisdom: “Don’t let your mouth write a check that you’re ass can’t cash.”
5. The Importance of Being Earnest by Oscar Wilde (1895). “The truth is rarely pure and never simple,” one character remarks in Wilde’s clever comedy about double identities. And white lies are even more complicated, as two young Englishmen of leisure learn when they try to avoid undesirable social obligations by claiming their noble services are required by needy (and imaginary) friends. When the worlds of their “friends” and fiancées collide, their confabulations turn to witty farce.
6. A Confederacy of Dunces by John Kennedy Toole (1980). “The funniest novel of the twentieth century,” says Donald Harington of this sprawling picaresque, which was awarded a Pulitzer Prize after Toole’s suicide. Its blustering, bumfuzzled antihero is Ignatius J. Reilly, an unintentionally hilarious, altogether deluded, and oddly endearing student of man who lives with his mother in New Orleans. Forced by a series of misadventures to finally find work, he endures stints as a pirate-clad hot dog vendor and a file clerk. As he meets strippers, lotharios, and other sharply drawn comic characters, Ignatius rants against the world’s stupidity and ponders his magnum opus, The Journal of a Working Boy.
7. A Midsummer Night’s Dream by William Shakespeare (1595). The summit of Shakespeare’s early romantic comedies, this play explores the troubled course of love leading to the marriages of King Theseus of Athens and Hippolyta, Queen of the Amazons, and two young aristocratic Athenian couples. The trouble begins when the king of fairies interferes with the Athenian couples via his agent Puck, who administers love potions to the wrong characters. The ensuing confusion is finally resolved in the fifth act as the royal marriage is celebrated by the performance of a hilarious piece of nonsense staged by simple guildsmen led by Bottom the weaver, whose dream gives the play its name.
8. The Ponder Heart by Eudora Welty (1954). In this comic monologue filled with witty Southern colloquialisms and vivid images, Miss Edna Earle Ponder, who manages a hotel in a small Mississippi town, describes her family’s wonderfully peculiar history. Her story focuses on her uncle, the eccentric and irrepressible Daniel Ponder, whose poor marriages created as many problems as his generous heart.
9. Blithe Spirit by Noël Coward (1941). As the Nazis bore down on Britain, Coward filled London theaters with this gay and witty farce about death. The sublime silliness begins when a writer holds a séance to research his novel on a murderous fake psychic. Who should appear but his first wife, dead these six years and none too happy about wife number two.
10. Right Ho, Jeeves by P. G. Wodehouse (1934). Including perhaps the funniest scene in the Wodehouse canon — Gussie Fink-Nottle’s drunken speech at the Market Snodsbury Grammar School — this madcap farce once again finds Bertie Wooster and his brilliant manservant Jeeves working to point Cupid’s arrows toward other hearts. Truth be told, newt-loving Gussie Fink-Nottle and droopy Madeline Basset belong together just as surely as Angela was made from Tuppy Glossop’s rib. After a series of gentle misunderstandings, Bertie and Jeeves may lift the scales from everyone’s eyes. Right ho!