I read Don't Get Too Comfortable in 2015, and covered it in a long, everything-I-read-that-month post. But this is the book before that; this is the one that introduced Rakoff to the world. Well, as much as anything did; he was a magazine writer so had been writing in public and getting attention for five years or so before this book came out in 2001.
So this is Fraud: a collection of essays about mostly topical things of the late '90s, from a deeply neurotic point of view, by a man now dead. It's still funny, I'm happy to say, but it does feel like it comes from another world these days: the world twenty years ago is not at all the world today. It was a sillier, lighter, more frivolous place...or at least it seemed so, to people who, like me and Rakoff, were relatively young then.
The loose through-line is given by the cover: Rakoff does present himself as incompetent in most aspects of modern life, but, really, this is a collection of magazine essays and This American Life pieces. It's all go-there, look-at-this-stuff reporting designed to be humorous, and it all succeeds pretty well. Rakoff was good at being funny, whether he's climbing a New Hampshire mountain, looking for fairies in Iceland, spending time with a group of new NYC schoolteachers from Austria, or returning to Tokyo (where he lived briefly soon after college).
If you like I-am-incompetent humor, from a New York point of view, Rakoff was very good at that at and very funny. And he's got at least two books in that mode - I still haven't read his third, Half Empty, which I hear is more dour and (not coincidentally) was written while he was unsuccessfully fighting Hodgkin's lymphoma, so I can't speak to that one.
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