"I'VE ALWAYS BEEN INTERESTED in narrators who could narrate," Sam Lipsyte tells me, on the phone from Manhattan. "Narrators who found, because everything else had failed them, that language was still something that they could wield with control and power."

In Lipsyte's hands, bitter, language-wielding failures are given free rein as some of the funniest fictional voices around. His 2005 novel Home Land is written as a series of increasingly bitter letters to a high school alumni bulletin, from the one unsuccessful alum whose exploits are guaranteed never to make print.

Lipsyte's newest novel, The Ask, is his most structurally conventional book to date. It is also his funniest—as though, once Lipsyte quit hemming himself in with experimental storytelling techniques, his peerlessly perceptive and endlessly inventive sense of humor was allowed to rampage unchecked.

"In the past I've been really interested in finding a device," Lipsyte explains. "I've always been fascinated with discovering some sort of container for the speech, for the language, so I wouldn't have to worry about structure so much. This one, I thought about some way to find that container, and I couldn't, so I felt like I would just take the leap and let the story go and see what happens."

When The Ask opens, protagonist Milo Burke is working as a development officer in the fundraising wing of a New York university—wheedling donations from art students' wealthy parents. "A solitudinous roil, my bitterness," muses Milo, once an aspiring artist himself. At the end of the first chapter, he's fired for shouting at a demanding, overbearing student: "My outburst was deemed hate speech, which called for immediate dismissal. I could hardly argue with them. I think it probably was hate speech. I really fucking hated that girl." Presently, though, he's invited to return to work for one final "ask," a potential donor who's specifically requested Milo's help. As Milo jogs off to do the new donor's bidding, Lipsyte packs the subsequent storyline with invariably hilarious observations on parenting, robot sex, the Iraq war, whether or not it's appropriate to masturbate with a baby in the room, and pre-school pedagogical theory. Few jokes are off limits—Lipsyte's got a knack for ferreting out the punchline in every subject he touches, and he's willing to touch just about anything.

"I don't sit down and say, 'Wow, I'm going to be so damn shocking right now.' This is just the stuff that bubbles up. Sentences start to veer toward these perhaps risky areas of discussion, and then I like to kind of play in the dangerous area, in the high-voltage zone," Lipsyte says. "What's off limits is just being cruel for the sake of cruelty. What's off limits is not presenting characters with as much dimensionality as you can. So the characters and the narrators can talk about anything, I don't really try to censor that, but I want it to be coming from some place organic in the work."

The Ask, for all the laughs it provides, doesn't begin to qualify as a feel-good read. (Unless it makes you feel good to laugh at how ridiculously fucked up the world is, in which case: Yes.) In his positive review of The Ask on Slate, writer Michael Agger poses what he calls "the Lipsyte question": "How useful, in the end, as a life strategy, is wallowing in bitterness?" I asked that question of Lipsyte in our interview. His response? "If I thought it was useful, I probably would not have written any books."