Published books of essays
Rakoff published three bestselling collections of essays, which include his own illustrations. Both Fraud (Doubleday 2001) and Don't Get Too Comfortable (Doubleday 2005) were awarded a Lambda literary award (which recognises excellence among LGBT writers who use their work to explore LGBT lives), both times in the "Humor" category. Half-Empty (2010) won the 2011 Thurber Prize for American Humor.
Fraud includes essays that are largely autobiographical and humorous. Rakoff stated, in relation to the theme of the book, "The central drama of my life is about being a fraud, alas." He went on to say "That's a complete lie, really; the central drama of my life is about being lonely, and staying thin, but fraudulence gets a fair amount of play." He has said that he thought of other titles for Fraud, like "Smart mouth" and "The jig is up". Rakoff described the first-person essays that comprise the collection as more inwardly focused than his later work. The work contains material from public radio's This American Life and from Outside and Salon, which was significantly lengthened and re-written, as well as a few new pieces.
The book received praise from many critics, garnering near-unanimous acclaim. In a review Publishers Weekly wrote that "a talented new humorist springs onto the scene: Rakoff has a rapier wit, slashing in all directions with slice-of-life insights and cutting remarks, sometimes nicking himself with self-deprecation in his dexterous duel with the American experience." Kevin Cowherd said that in the book, Rakoff "makes a strong bid for the title of Most Neurotic Man on the Planet, and the results are absolutely hilarious – when they're not achingly revealing and tinged with sadness." Max Magee called the collection a "meta-article in which he talks about the particulars and relative merits of his assignment as he embarks on that assignment" and that "the reader feels invited in for a behind the scenes look at what it is like to be a disaffected, overly-qualified, under-ambitious journalist as he takes on his fluffy assignments." David Bahr calls Fraud "witty, insightful and typically bittersweet."
Other reviews of the book and audio-book were mixed. The reviewer in The New York Times mentioned (by way of criticism) that Sophocles and Freud had pursued the same idea that forms the book's focus, that is, that we are defined by our fears. Greil Marcus said Rakoff's stories are not as funny as those he read on the radio.
Don't Get Too Comfortable, which is subtitled "The Indignities of Coach Class, The Torments of Low Thread Count, The Never-Ending Quest for Artisanal Olive Oil, and Other First World Problems" was published in 2005 and also consists of comical autobiographical essays. Some of the essays were originally published in shorter form elsewhere and some original. The over-riding theme of the articles is the absurdity and excessiveness in American life: the book is about luxuries and privileges being treated as deserved rights. Rakoff said that the moral of the book is that there should be "a little more guilt out there" and "we could all, myself included, count our blessings, acknowledge our privileges." The book was generally praised by critics. The New York Times said, "Rarely have greed, vanity, selfishness, and vapidity been so mercilessly and wittily portrayed". Emily Gordon says that in his "bursts of pure enthusiasm, he's a delectable Cole Porter, Nicholson Baker and Sarah Vowell smoothie". However, Rakoff was criticised in The Washington Post for misusing the word "like", with the reviewer suggesting that Rakoff's prose could use tightening. In The New York Times, Jennifer 8. Lee said the book was "no more than a collection of vaguely related magazine pieces" rather than "a coherent seriocomic manifesto", that some essays were off-theme, and not about narcissism and excess.
A third book of essays, Half Empty was published in September 2010. Rakoff said the book is "essentially about pessimism and melancholy: all the other less than pleasant to feel emotions that because they are less than pleasant to feel have been more or less stricken from the public discourse but in fact have their uses and even a certain beauty to them". The book won the 2011 Thurber Prize for American Humor.
