Singing 21st-Century Blues

By Michael Miller

Near the end of Sam Lipsyte’s wonderful fourth novel, The Ask (Farrar, Straus and Giroux, 2010), protagonist Milo Burke considers sending out résumés in a terrible (and familiar) economy. “You could still get lucky,” he says. “Couldn’t you?”

He doesn’t give an answer. Certainly for Milo, luck ran out a long time ago. A failed artist that curses his previously intellectual existence as—only in his mind—the “new sensation” in painting, Milo is recently unemployed from his dead-end job in the development department at a dead-end university (or, as Milo calls it, “Mediocre University at New York City”), asking rich people who just lost their cash after the bottom fell out of the dead-end economy to donate money.

Lipsyte has been exploring the semiotics of sloth since the comforts of a stable economy were still, well, stable. In The Ask, though, the stakes are higher. We’re not just reading about some lovable fuck-up, but about a guy who’s had a long, strange fall—never quite good enough to chase after his dreams, whose retreat into domestic bliss as a husband and father now requires an even more difficult retreat into maturity.

Milo, directionless, self-pitying and a burgeoning alcoholic, attempts to redeem himself through his wife and child. His love for them is touching and sincere, but the gentle balance Milo has found with his nuclear family is corrupted by all those conditions that are the source of his problems to begin with—late capitalism, an existence in which any event is a possible future blog post, where the question is not “What does it mean?” but “How can I say it in 140 characters or less and Tweet it to all my friends?”

His life falling apart, Milo is surprised one day by a call from his former employer at “Mediocre University at New York City.” His old college roommate, Purdy Stuart, now a man wealthy beyond imagination who stays up all night eating candy because he’s too old to do coke, wants to give a donation to his wife’s alma mater. Purdy wants to work with someone he trusts. Milo is hired back to do this one last task: Make sure the rich guy forks it over.

With Milo, Lipsyte has written a character so filled with rambling, incurable insecurity that you can’t help but respect the extent of his self-pity. He read Foucault at his snooty liberal arts college, thought he was a saint for it, painted with precise technique and slept with girls with tongue rings only to find himself a victim of domesticity. He wishes he were chained to a desk at work because then he’d at least have a job.

With this novel, Lipsyte has proven himself to be one of the most unapologetic voices of contemporary literature. He mines the sexual frustration of Philip Roth, combines it with the paranoia of Don DeLillo and fills the space in between with a cast of characters as absurd and enigmatic as anything in a Thomas Pynchon novel.

The Ask is a hilarious book about failure—a scathingly unhappy comedy obsessed with a culture that’s obsessed with obsessions. Milo is long past his prime, but the pathetic state of his life is also a metonymy for a confusing time, an age of “epic, epochal fuckedness,” in the words of one of Milo’s co-workers. Lipsyte has found the humor in this horror. “No more did I pine aloud for that time in my past when I had a future,” Milo says. It’s funny because it’s true, at some point, for all of us.

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