One thing should be made perfectly clear: this collection of fifteen dryly humorous essays has a very distinct audience, and if you're not a part of it, your enjoyment is likely to be lessened. The ideal reader of this book is a well-off white city dweller (ideally a Manhattanite) who likes to listen to NPR (especially "This American Life"), reads the New York Times magazine, Salon.com, etc., and is a fan of David Sedaris, Sarah Vowell, Amy Bloom, and Dave Eggers -- all of whom blurbed this book. This is not to say that _only_ readers who fit this profile will enjoy the essays, but they certainly seem pitched for that particular audience. Since I'm at least somewhat in that audience, but far from an exemplar of it, it should come as no surprise that I found the essays fairly mixed.
About half the essays traffic in the tried and true "fish out of water" framework, in which the quasi-effete Rakoff is sent to cover some event or do something that's totally at odds with his nature: "In New England Everyone Calls You Dave" (in which he visits New Hampshire to climb a small mountain with a local character), "Including One Called Hell" (in which he attends a New Age seminar fronted by noted thespian and lama Steven Seagal), "Hidden People" (in which he visits Iceland to talk to people about faeries and gnomes), "The Best Medicine" (in which he visits Aspen to cover the U.S. Comedy Arts Festival), "I'll Take the Low Road" (in which he visits Scotland to go to Loch Ness), "Back to the Garden" (in which he attends a wilderness survival school), and "Tokyo Story" (in which he revisits Tokyo, the site of his 1986 nervous breakdown). Some of these are quite good, especially the New Age seminar and wilderness survival ones (although in the latter, his behavior is notably at odds with how he casts himself in other essays). Others are rather lackluster, especially the visits to Iceland, Loch Ness, and Japan -- which read like standard issue travel magazine articles.
The other half of the essays are more personal, as Rakoff mines his own life for material. Here we learn of formative experiences: "Arise, Ye Wretched of the Earth" (the teenage stint on an Israeli kibbutz which leads to his realization that he's gay ), "Lush Life" (his stint as an overworked, underpaid New York publishing scene editorial assistant), "Before and After Science" (his youthful stint working as a teenager in a Swensen's franchise owned by a Greek couple), "Lather, Rinse, Repeat" (his one-time appearance on a soap opera), "Extraordinary Alien" (his application for green card -- Rakoff is Canadian), "Christmas Freud" (his seasonal stint as a department store window prop), and "I Used to Bank Here, But That Was Long, Long Ago" (his history with sperm banking). These are all well-written, generally witty reflections that are enjoyable if you are the kind of reader who finds the introspection of others interesting fodder. Others will find his autobiographical stylings just so much navel-gazing. I found myself caught in the middle between some genuinely funny lines and some genuinely self-pitying whining (especially in "Lush Life").
Despite the reflective nature of a good part of the material, Rakoff is a humorist at heart -- albeit of the neurotic Woody Allen variety. While he's got plenty of cynical venom for others (although not nearly as much as Sedaris), he dilutes this with heavy doses of self-deprecation. And like Allen, sometimes he's exceedingly funny, but often, a little of his affected style often goes a long way and attempts at profundity veer dangerously close to parody. Some readers may find his highbrow vocabulary somewhat off-putting and pretentious, I didn't notice it that much one way or the other. But be forewarned that the essays are sprinkled with allusions to Baudelaire, Myrna Loy, Preston Sturges, Robert Moses, and other personages not necessarily familiar to the Average Joe. On the whole, these are essays worth dipping into, and if you like one, you'll probably find at least others you'll like. It's not brilliant stuff by any means, but worth trying.