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His first piece is a typical mix of humor, absurdity and pathos. The Great Zucchini (real name, Eric Knaus) works weekends and makes a six-figure income entertaining kids, but Weingarten follows him around long enough to observe his darker side. The Great Zucchini lives in a largely unfurnished apartment (with an empty fridge) and "for the last several years, The Great Zucchini has been in debt to bookies." His private life is completely disorganized: "When the lights go out, it's time to pay the [overdue electricity] bills."

The Great Zucchini is himself an overgrown kid, but Weingarten fully admires his genius as an entertainer, quoting rival Broccoli the Clown: "He's got an incredible rapport with the children. ... The guy relates amazingly to kids. He understands and enjoys them."

Weingarten again explores the dark depths beneath humorous surfaces in his brilliant profile of cartoonist Garry Trudeau. The two men share a similar attitude about humor: "humor springs from existential pain -- from a need to blunt the awareness that life is" uncertain and supremely difficult. He shows us Trudeau mining that pain in his work, a comic story line that follows a U.S. soldier (an amputee) returning from Iraq. Trudeau, like Weingarten, mixes light and dark to produce something surprisingly revelatory.

Some of the pieces are straight funny, such as when Weingarten visits France around the time of the 2003 Iraq invasion in search of anti-Americanism. The French he meets repeatedly express a genuine admiration for the American people, alongside a vocal loathing for our political leadership, especially President George W. Bush. Weingarten is determined (yet fails) to provoke French anti-Americanism, as when he asks a popular French chef whether "you agree that American chefs are better than French chefs because they give you more food?"

Whether he's going in search of a long-lost crush, trying to locate "the armpit of America" (it's in Nevada), or observing how stressed subway commuters respond as violin impresario Joshua Bell plays for spare change (they barely respond at all), Weingarten winningly combines humor and profundity in a way that keeps readers wanting more.

Chuck Leddy is a member of the National Book Critics Circle and reviews books for the Boston Globe and B&N Review.