If what hooked you in Breakfast of Champions was Vonnegut strolling into Midland City, talking directly to you, and even "releasing" Kilgore Trout, Calvino’s If on a winter’s night a traveler will feel like catnip. It casts you as the Reader, breaks and restarts itself in ten different beginnings, and constantly winks at the way stories get made—much like Vonnegut’s diagrams and asides about his characters’ fates. You’ll get that same sly, author-as-puppeteer thrill—only this time the strings are attached to you.

You laughed (and winced) as Vonnegut skewered ad men, car dealers, and the arts festival hoopla around Dwayne Hoover and Kilgore Trout, with definitions of brands and bodies turning into jokes about America. Catch-22 takes that same absurdist knife to military bureaucracy: Yossarian wrestles with a rule that traps him in an endless loop, while Milo Minderbinder turns war into a business venture. If Vonnegut’s mock-instructional tone and looping gags hit your sweet spot, Heller’s circular logic will have you cackling—then reeling.

If Dwayne Hoover’s breakdown—told with a deadly straight face—and Kilgore Trout’s shabby misadventures made you laugh in spite of the awfulness, A Confederacy of Dunces offers that same uneasy, hilarious edge. Ignatius J. Reilly blunders from Levy Pants to a doomed hot dog cart, detonating lives with every pompous rant. Like Vonnegut’s bleak jokes about chemicals in the brain and America’s flimsy myths, Toole folds tragedy into farce so deftly you’ll be grinning right up to the gut-punch.

Loved Vonnegut’s crude drawings, arrows, and deadpan definitions that literally change how you read the page? Pale Fire pushes form even further: a 999-line poem by John Shade annotated by the wildly unreliable Charles Kinbote, whose footnotes hijack the narrative. As Vonnegut’s marginal doodles and authorial stage directions reshape Breakfast of Champions, Nabokov’s commentary turns the book into a puzzle you read along the gutters—funny, unnerving, and brilliantly constructed.

If you liked how Breakfast of Champions hopscotches through Midland City—dropping into side characters, then swinging back to Kilgore Trout and Dwayne Hoover—Winesburg, Ohio is the granddaddy of that approach. Anderson’s linked portraits circle George Willard and a gallery of “grotesques,” each vignette exposing private contradictions with the same plainspoken sting Vonnegut uses when he pauses to explain an ordinary object and it becomes a joke—and a wound.