THE BOOK’S COVER looks like a child’s cartoon: a smiling bunny and a chipmunk, a boy in a boat on a pond, two bluebirds holding up a banner. Only the banner reads “Half Empty” and in the far background sit two volcanoes, one smoking, the other exuding lava.

David Rakoff’s Half Empty also bears the message: “WARNING ! ! ! No Inspirational Life Lessons Will Be Found In These Pages.” 

This is so. The collection of 10 essays by one of our most gifted and most mordant writers begins with “The Bleak Shall Inherit,” an expansion on this warning and a reassurance that all the pop psych suggesting we’re better off when we’re happier is effectively trumped by experience. (And by some pretty persuasive research, notably in psychologist Julie Norem’s The Power of Negative Thinking.) In “The Bleak,” as in his other essays, Rakoff conspires to let us in on his secret life, offering the knowledge that one can never overestimate human folly, or the likelihood that Murphy, with his one eponymous law, was an optimist. Rakoff’s third essay is called “The Satisfying Crunch of Dreams Underfoot.”

Cynics and satirists often craft the best lines, and Rakoff has more than his share. Take, for instance, this description of being in Salt Lake City to visit the Mormon sites:

My room is cheerfully located between the sixth-floor elevators. The springs of my bed wheeze. The elevator dings. The ice machine right outside my door rumbles its icy bounty, a steady tattoo that beats, “Stay up! Stay Up!” I am in a canvas that Edward Hopper never felt bummed out enough to paint.

The best line in the book, however, cannot be repeated here: it would be a spoiler. Close to the perfect putdown, it is, alone, worth the price of admission. It is the last line of a slyly constructed piece, the premise of which is this: Rakoff is cast in a minor role in, and then dumped from, a movie with a script based on a novel by a writer he clearly loathes. He tells us, “She might be the only person in my life about whom I’ve said something purposely, gratuitously injurious and deeply unkind.” Thereafter, we get a catalog of unkind words about the woman, not a single one of which, Rakoff tells us, is the one he had in mind.

But Rakoff is more than an adept writer; he is also an incisive reporter: a gift he attributes, as the child of therapists, to his innate abilities as a listener. The essay “I Feel Dirty,” about New York’s first Exotic Erotic Expo and Ball, which far-less-than-fills a huge pier along the Hudson, showcases his talent for observation. The Expo begins optimistically, but ends blankly, with Rakoff noting that the ball’s founder has, for the past two years, practiced abstinence: “I’ve had threesomes, foursomes, orgies, and I’ve stepped back. It’s interesting. I look at people and things in a different light.” Rakoff also writes brilliantly about Disney’s House of the Future, and about Rent as a musical about self-absorbed whiners.

His persona is that of the cynic, but one supposes Rakoff knows this line from Robert Anton Wilson: “Cynics regarded everybody as equally corrupt… Idealists regarded everybody as equally corrupt, except themselves.” Rakoff, then, cannot regard himself wholly as a cynic; there is, deep down, humanity within him. The last two essays, about personal pain and mortality, come awfully close to redeeming the man.

This is Rakoff’s third book, after Fraud and the highly regarded essay collection, Don’t Get Too Comfortable. May there please be more.