The Long Ships by Frans Gunnar Bengtsson (NYRB Classics, $18). Humor, like salt, makes everything better. I consider it required seasoning for any piece of writing, which is why the first title in this list of my favorite unlikely comedies is this 1955 novel about Vikings. Frans Gunnar Bengtsson wryly captures the silliness of a world in which both the problems and the solutions are men swinging axes.
A Confederacy of Dunces by John Kennedy Toole (Grove, $16). Ignatius J. Reilly is the most original, most difficult, most worldview-havingest character ever created. Here he is on page six: "I am at the moment writing a lengthy indictment against our century. When my brain begins to reel from my literary labors, I make an occasional cheese dip." This Pulitzer Prize-winning book is my favorite novel. I wish I could quote it all for you here.
Lolita by Vladimir Nabokov (Vintage, $16). There are a lot of reasons to love this book; my reason is the scathing arrogance of its narrator, Humbert Humbert.
Cat's Cradle by Kurt Vonnegut (Dell, $16). Vonnegut's fourth novel was, I think, the first "serious" book I ever read. There's so much humor in the blackness, though. I've read every other Vonnegut book since, but this satire on the nuclear arms race remains my favorite.
Raise High the Roof Beam, Carpenters by J.D. Salinger (Little, Brown, $8). This novella about a wedding day when the groom goes missing was originally published in The New Yorker and is part of Salinger's Glass family saga. (It's paired in paperback with a later novella, Seymour: An Introduction.) Because the narrator is looking back on the events described, Seymour Glass' subsequent suicide hangs over the book, but there are brilliant deadpan lines throughout.
Lucky Jim by Kingsley Amis (NYRB Classics, $15). I never went to grad school, and Amis' novel about an underachieving medieval history lecturer at a second-rate English university confirmed me in that decision. Jim Dixon also helped me discover the magic satisfaction of imagining pushing peas up people's noses.
—Christian Rudder is a co-founder of the dating site OkCupid and the company's former president. His recent book Dataclysm, a lighthearted tour of the things we reveal about ourselves when we go online, has just become available in paperback.