Drop what you’re doing right now, and read Sam Lipsyte’s The Ask.  See other entries in this series here.

In my senior year of college, I co-taught a creative writing seminar called “Books that Make You Want to Write” with my adviser, James. While poring over what books to cover, we shared the following dialogue:

James: “Dude, we should read Home Land. There’s a scene where the main character leaves his girlfriend so she can smoke crack alone in a hotel room, and another where he’s having sex with her and says, ‘I’m your dead brother Lenny!'”

Me: “I have no idea what you’re talking about, but I agree wholeheartedly.”

It was love at first referral, and I discovered one of the wittiest writers of my experience. Sam Lipsyte specializes in characters who suffer from broken filters between their brains and their mouths. Labyrinthine inner monologues will frequently spasm into a protagonist’s daily discussions, much to the confusion of those around him and the thoughtful laughter of the readers.

Sam has finally released his latest book, The Ask. It’s about an artist (Milo) who’s settled down to work for a university, and must beg its wealthy patrons for donations. He runs the risk of losing his job if he doesn’t convince an old friend to make a huge give, but has to tangle himself in a broken web of illegitimate children, morally bankrupt capitalism, family chaos, and a re-evaluation of the “American” way to make it work. Milo shares many qualities reminiscent of the protagonist in Home Land, but with the added strains of a family to support and expectations of success.

This is a worthy book that had me busting out laughing in some parts and fuming with anger in others. I could compare it to a Coen brothers’ movie for its complexity and absurdity, but the Coens don’t write dialogue this well. Lipsyte is one of the best out there. I get a palpable sense of comfort whenever I submerge in his narrative voice.

The Ask is structured in chaos. Half-unemployed Milo wanders New York, reconnecting with old friends and making new ones, sharing philosophies on existence while scrambling to solve everyone’s problems at once. His mortally cynical compatriots each have unique, entertaining, and sometimes heartbreaking worldviews to impart. Milo listens to each with Buddhist patience, all the while struggling to find his place somewhere in the midst of family, career, and art. This book left me with an emotional resonance for our protagonist’s struggle and an aching gut from the laughs that took me there.

I can’t guarantee that you’ll be a better person for reading The Ask, but you will be on better terms with your dark and underachieving side. You will realize that we are all victims of our parents, and that life is about flies tapping against a window pane. Some flies just tap higher up than others.

Similar books you will also enjoy: Home Land and The Subject Steve by Sam Lipsyte, Survivor by Chuck Palahniuk.