The Big Uneasy

"Melancholy seems to be both a feeling and a feeling about a feeling," David Rakoff says about one of two major themes--the other, pessimism--in Half Empty, his new book of essays. "It's the kind of thing where you watch yourself listening to Rickie Lee Jones in the mirror. It's a very 14-year-old girl kind of state of being. It's not without its pleasant aspects."

Rakoff is especially adept at weaving gratifyingly gloomy tapestries from the loom of bad judgment and calamity. In "The Bleak Shall Inherit," the Toronto-born New Yorker points to just missing the Internet boom at a tech firm: "I had walked away from a job at what would undoubtedly have been the wildly lucrative ground floor (1986, Tokyo) because it had seemed so boring." In "The Satisfying Crunch of Dreams Underfoot" he describes elation at being plucked from obscurity (a desk job in publishing) to play a small part in the film The First Wives Club. "I cashed in all my vacation days, thinking as I left the office, I'll be back... To clean out my desk! Suckers!" But he was soon fired from the movie--to be replaced by Bronson Pinchot--and missed his only opportunity to befriend Bette Midler and fulfill a fantasy of staying up all night at the piano with her.

Rakoff says he is more or less comfortably resigned to the notion that his somewhat grim outlook is more a fixture than a phase. "Everyone says, 'Live in the moment! Enjoy it!' " he says. "Well, there is no joy in being an unrealistic Pollyanna. That someone would say, 'Everything is going to be great from now on. I've got a terrific career, and everything will always be fantastic!'--that person makes me anxious. It makes them seem like a moron. It's terrifying to be around people like that."

Rakoff, who has two previous essay collections, Fraud and Don't Get Too Comfortable, isn't an unremitting pessimist. Recently diagnosed with cancer--caused by radiation treatment received for Hodgkin's disease two decades earlier--he has a reserved buoyancy: "I'm generally optimistic that things will ultimately kind of work out OK for me." And though he's in treatment, he's focusing on the most important issues. "I might be the cutest patient on the floor, a dubious honor in a cancer ward," he writes in the essay "Another Shoe."

His book tour kicks off September 21, and fans in attendance might do well to say they drove to see him. "I remain immensely grateful in the thought that someone drove somewhere to see me," he says. But he may be thinking of the effort it would take him to reciprocate. "I can't drive, so it would require quite a bit. I'd have to go down and replace my Social Security card, because I lost it when I got mugged in 1988, so there's that. Then I'd have to take drivers' ed. Then I'd have to find a car. I'm always mindful of that when people show up for readings."