City Boy sat on my shelf for many years before I read it. Then I picked it up one day, and it was awesome. I love and hate when that happens. Love, because it means my bookshelves contain lots of gems. But sometimes I have to sift through lots of Fool’s Gold before finding the diamonds, if you get my drift.
In City Boy, “city boy” Jack Orlovich longs to become a writer. So to pursue his dream, he moves with his wife Chloe from the suburbs of southern California to the bustling mecca of Chicago. The novel opens with Jack and Chloe moving into a new apartment and meeting all their new oddball neighbors. We also get an intimate glimpse into Jack and Chloe’s dynamic. They seem to have lots of arguments, affairs, and intense make-up sessions.
Jack is the voice of the novel, but it’s all the other characters in City Boy that give the novel its pizazz. Chloe is beautiful, compelling, and doomed. Ivory is a sadistic crippled girl who wants to seduce Jack. There’s a few other eccentric characters, but I think City Boy feeds mainly off the relationships between Jack and these two women.
All in all, City Boy is really about Jack’s journey to becoming a writer. It has a quirky tone, and there’s an unforgettable gut-wrenching part where fireworks make someone lose a limb. There’s also a gross, disturbing affair between Chloe and her nasty, disgusting coworker.
I think Jack and Chloe would have been okay if they had they only communicated with one another and demonstrated simple acts of love and kindness.
City Boy is a bittersweet train wreck. It’s pleasurable, charming, and fun. Not too heavy, and just witty and sarcastic enough to keep you hooked til the end.
Other books by Jean Thompson include:
- She Poured Out Her Heart (2016)
- A Cloud in the Shape of a Girl (2018)
- The Poet’s House (2022)
What did you think about City Boy?
Last Updated on January 16, 2026 by Sarah Ann
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