Sam Lipsyte, 41, may be America's greatest living literary black humorist. His latest novel, The Ask [Farrar, Straus and Giroux, $25], chronicles the painfully hilarious failures of Milo Burke, an unsuccessful middle-aged painter (not to mention husband and father) with a dead-end job in university development, one that he will lose unless he can persuade an impossibly wealthy former schoolmate to donate a ton of money to his employer. The humiliations only grow more intense from there.

Q: You go to some pretty dark areas in the book. Is it difficult to write about that kind of subject matter without wanting to hurt yourself?
A: I think maybe I write books so I don't hurt myself.

Q: You started the book five years ago, but it predicts today's terrible economic situation very accurately. How were you able to be so prescient?
A: Well, I have a wizard who visits me. I guess I feel that, you know, the economy's always shitty for me. So I just wrote it as a time in the now slash near future when things weren't going so well, and as I was writing things really did fall apart.

Q: Did you take any pleasure in that, if only because it made your book more relevant?
A: [Laughs] No, I'd never . . . I'd trade economic vitality for millions and billions of people and take back the book. No, but I was writing from the vantage of someone who's always going to be struggling on some levels. Things are falling apart across the board, and the rich are sort of taking a hit, too, but they're still the rich.

Q: Did you ever work in development yourself?
A: No. I made it all up. All you really need are a couple of phrases that you've overheard and then you can sort of run from there. So for me, I heard someone talking about "the ask" in relation to fund-raising and the "big give" that was to be forthcoming, and I didn't really need anything else. I've worked in offices, I've been around all kinds of people, so I feel that I was able to be inventive. And I hope that no one who is trying to get into development or fund-raising is going to read my book for research.

Q: Your books have been critically acclaimed and won awards, but commercially you've remained kind of a cult writer. How do you feel about that?
A: It's funny, because when I was twenty I fantasized about being a cult writer, and now I think, What the fuck was I thinking? You romanticize it as a young person, and you stand with your little cult author off in the corner and sneer at all the mainstream success. Then you get older and you get sad about it all.

Q: So you'd take the Nicholas Sparks route if you could do it all over again?
A: That's really what I'm working on now. It's not over for me! Nicholas Sparks, I'm coming for you.

Q: Yes, there's still room for another novel revolving around misplaced love letters.
A: The Slob Whisperer. The thing is, I don't mean to complain: I'm really fucking happy that my books get published. That's the bottom line. I've got a job, my books are getting published. Everything's fine. I'll take the cult.