Early career
Before becoming a full-time writer, Rakoff worked for 13 years in the publishing industry, including as a publishing assistant and a publicist. He worked at a literary agency for 3 years and then as an editor and communications manager for HarperCollins, where he worked for 9 years. For a period starting when he was 25, Rakoff wrote as a freelancer while working in the publishing industry. Eventually he was able to earn a living from his writing, he became a full-time writer in 1998.While Rakoff was working in publishing, he wrote Q and A interviews entitled "The Way We Live Now", which appeared in the
New York Times Magazine from 1999—2002.
Role of David Sedaris and Ira Glass in Rakoff's career
Rakoff has said that he owes David Sedaris and Sedaris's producer, Ira Glass, his whole career, Rakoffwrote to Sedaris in 1992, after hearing him read on the radio his essay about being a Christmas elf, which was to make him famous. That day, he wrote to Sedaris immediately to ask if he could publish Sedaris's works (which he later confessed he had no intention of doing, since he was desperate to leave publishing). They became friends, with Rakoff doing work in the theatre with Sedaris, first directing a play written by Sedaris and his sister Amy Sedaris, and later acting in their plays. Through Sedaris, Rakoff met Ira Glass, who was then a junior reporter on the Morning Edition program. When Ira Glass began
This American Life, Rakoff became involved with the new show at its inception. Sedaris encouraged Rakoff to go on public radio, where Sedaris himself achieved fame: at his urging Rakoff took work to
This American Life , starting with "Christmas Freud", an account of Rakoff's job impersonating Sigmund Freud in the window of Barney's department store during the holidays.
Journalism
Rakoff is a prolific freelance writer and has been a regular contributor to
Conde Nast Traveler,
GQ,
Outside Magazine and
The New York Times Magazine. His writing has also appeared in
Business 2.0,
Details,
Harper's Bazaar,
Nerve,
New York Magazine,
Salon,
Seed,
Slate,
Spin,
The New York Observer,
Vogue,
Wired and other publications. He has written on a wide and eclectic range of topics.
Published books of essays
Rakoff has published two 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.
Fraud
Fraud includes essays that are largely autobiographical and humorous. Rakoff states, in relation to the theme of the book: "The central drama of my life is about being a fraud, alas". (He goes 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 has described the first person essays that comprise the collection as more inwardly focussed 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" and 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 also 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
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 absurd and excessive in American life: the book is about luxuries and privileges being treated as deserved rights. Rakoff has 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.
Half Empty
A third book of essays,
Half Empty was published in September 2010. Rakoff has 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". Rakoff argues that it is "a defence of melancholy, pessimism, anxiety and all of the emotions that have been tarred with the brush of negativity and therefore stricken from the larger cultural conversation. I hope to argue...that, while these emotions may well be hedonically less pleasant, they remain necessary and even beautiful at times."
Contributions to anthologies
Rakoff has also contributed essays to the following anthologies of non-fiction published by other writers:
- "My first New York" in My First New York: Early Adventures in the Big City (As Remembered by Actors, Artists, Athletes, Chefs, Comedians, Filmmakers, Mayors, Models, Moguls, Porn Stars, Rockers, Writers, and Others) (2010) (edited by New York Magazine) (2008) (See extract here )
- "Utah" in State by State: a panoramic portrait of America (2008) (edited by Matt Weiland and Sean Wilsey) (See extract here )
- "Streets of sorrow" in The Best American Travel Writing 2007 (2007) (edited by Susan Orlean) (See extract here )
- "Love it or Leave it" in The Best American Non-required Reading 2006 (2006) (edited by Dave Eggers) (See extract here )
- "Barbra's farewell: A city Verklempt" in Da Capo Best Music Writing 2001 (edited by Nick Hornby and Ben Schafer) (See original article here )
- "My sister of perpetual mercy" in A member of the family: gay men write about their families (1992) (edited by John Preston)
- "Christmas Freud" in The dreaded feast: writers on enduring the holidays (2009) (edited by Michele Clarke and Taylor Plimpton)
- The autobiographer's handbook: The 826 National Guide to Writing Your Memoir (edited by Jennifer Traig and Dave Eggers)
Rakoff has also contributed fiction pieces to the following anthologies:
- "Sagrada family" in Men on men 5: best new gay fiction (1994) (edited by David Bergman)
- Interview as a child prodigy in The infant mind transcript/The infinite mind (published by Lichtenstein Creative Media).
Radio essays
Rakoff has been a regular contributor to the radio program
This American Life on Public Radio International, in which each week writers and performers contribute pieces (some documentary, some fiction) on a chosen topic, usually in the first person. The first was "Christmas Freud", an account of Rakoff's impersonating Sigmund Freud in the window of Barney's department store during the holidays. The piece appears in
Fraud, his first collection published in 2001. He says that
This American Life let him have his own take on things and break the bounds of just being a journalist. Most of his radio performances are recorded, but some are performed live. Rakoff is the only person to host a
This American Life episode in place of Ira Glass (the episode being "Like It Or Not"). He appeared in
This American Life: Live! (2008) but was cut from 2009 version (the video with Dave Hill is available on the internet. Rakoff can also frequently be heard on the CBC radio program
WireTap.
Screenplays
Rakoff adapted the screenplay for the Academy Award winning short film "The new tenants", originally written by Anders Thomas Jensen. The director Joachim Back described Rakoff's role as having "helped me with the dialogue" and having "collaborated a lot on the dialogue". He also appears in the film. The film won the 2010 Oscar for best live action short film. Rakoff has sold what he calls a "meta screenplay", written with Mr Dave Hill, based on a fictitious tour to publicise the book
Don't Get Too Comfortable. In a short film based on the same story, Rakoff plays a high-maintenance author opposite Dave Hill's patient, accommodating publicist. The film is available on the internet.