David Rakoff was born on November 27, 1964 in Montreal, Quebec, Canada. He is the youngest of three children: his brother, the comedian Simon Rakoff, is four years older than David and their sister Ruth, a family-conflict mediator, is the middle child. David Rakoff has said that he and his siblings were close as children. Rakoff's mother, Gina Shochat-Rakoff, is a doctor who has practised psychotherapy and his father, Vivian Rakoff, is a psychiatrist. Rakoff has written that almost every generation of his family fled from one place to another. Rakoff's grandparents, who were Jewish, fled Latvia and Lithuania at the turn of the 20th century and settled in South Africa. The Rakoff family left South Africa in 1961 for political reasons, moving to Montreal for seven years. In 1967, when he was three, Rakoff's family moved to Toronto. As an adult, he says that he identifies as Jewish.

Rakoff attended high school at the Forest Hill Collegiate Institute, graduating in 1982. In the same year he moved to New York City to attend Columbia University, where he majored in East Asian Studies and studied dance. Rakoff spent his third year of college at the School of Oriental and African Studies in London and graduated in 1986. Rakoff worked in Japan as a translator with a fine arts publisher. His work was interrupted after four months when, at 22, he became ill with Hodgkin's disease, a form of lymphatic cancer which he has referred to as "a touch of cancer". He returned to Toronto for eighteen months of treatment, including chemotherapy, radiation, and surgery.

From 1982, Rakoff lived in the United States, first as a student, then as a resident alien. In the early 1990s he was issued a green card, a subject he wrote about in one of his early newspaper articles. After twenty-one years living in the United States, Rakoff applied for dual Canadian-American citizenship, primarily because he decided he wanted to be part of the political process. Rakoff chronicled the experience of becoming an American citizen in an essay published in Don't Get Too Comfortable. He obtained dual Canadian-American citizenship in 2003.

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.

Rakoff has said that his first career choice was to be an actor: he has written "like generations of other misfits before me, be they morphological, sexual or otherwise, I decided that I would make theatre my refuge". Rakoff performed in the theatre at university and acted while working full-time in the publishing industry and later while freelancing as a writer. For instance, he performed at the first US Comedy Arts Festival in 1995 in a play written by a friend. He has said that he likes acting because it involves other people, unlike writing. However, his self-assessment of his acting ability was "as it turns out, I'm a deeply uncompelling camera presence".

Despite his ambitions as a child, he has said that he only pursued acting half-heartedly, partly because his family was against him being an actor and partly because of the stereotyping that unimaginative casting agents engage in. Rakoff has characterised most of the roles that he auditioned for as "Fudgy McPacker" or "Jewy McHebrew" (to which he later added "Classy McSophisticate"). Fudgy McPacker is a stereotypically gay character, who is either supercilious or the loveable queen and Jewy McHebrew is the prototypical Jewish part, involving a careworn, inquiring, furrowed browed, bookish type. Rakoff has said that he has continued with his theatre work, since such acting stereotypes are not so prevalent in stage work, because audiences are more sophisticated, and there is not as much money at stake, meaning that there is not such risk-averse casting. He has also noted that, as a writer, being gay and being Jewish does not limit his readership or the subjects he can write about in the way it limits his acting roles.

Film

Rakoff has appeared in several films, although he has noted that almost invariably his part is left on cutting room floor: "I’ve been cut out of some very august projects", he has said. For instance, he worked on The First Wives' Club (1996), but his scenes were deleted in favour of Bronson Pinchot’s. Rakoff’s first major film role was in A cloud in trousers, a short film by Gregg Bordowitz (1995) which appeared on public television, with Rakoff playing Vladimir Mayakovsky on whose poetry the film was based. His subsequent film appearances include performances as a librarian in Cheryl Dunyé’s film The Watermelon Woman (1996), an appearance by the back of his head as Ben Baron, who is dismissive to Harper Lee, in Bennett Miller’s Capote (2005), a non-speaking role as Boswell in Paul Dinello’s Strangers with Candy (2005) (which was co-written by Amy Sedaris), and roles as a publishing boss in Bad Bosses Go to Hell (1997) and as a duplicitous director in Alison MacLean’s film Intolerable.

Rakoff can be seen in the Academy Award winning short film The New Tenants (2009). In the film he plays Frank, half of a gay couple who move into an apartment that was vacated unexpectedly. The film begins with Rakoff delivering a bitter, humorous but pessimistic monologue on life and death. Rakoff also adapted the screenplay for the film.

Rakoff has appeared as himself in the documentary "Florent: Queen of the Meat Market" (2009) about a local restaurant and in a film about the book "State by State" (2008), in which one of his essays is published.

Television

Rakoff appeared as a modelling agent Rich Tuchman in As The World Turns, a television soap opera. He wrote about that experience in the essay "Lather, Rinse, Repeat", published in the collection Fraud. He also appeared as Todd in Cosby (1996—2000) and as Frank in the TV show Snake 'n' Bacon (2009).

Stage

Rakoff has acted in the theatre, including off-Broadway, notably in plays written by The Talent Family (David and Amy Sedaris). Those plays include the Obie award-wining One Woman Shoe 1995), in relation to which a critic writing in Newsday said that Rakoff "exuded quirky appeal", the New York Times said both that Rakoff was "hilarious" and that he delivered "a droll, impeccably sustained performance providing the necessary anchor". Rakoff also appeared in the Sedaris's The Little Freida Mysteries at La Mama (1997), of which the The New York Times said Rakoff was part of a "deft ensemble", and which received a good review in Newsday. and in The Book of Liz (2001), in which he played various characters, including Nathaniel Brightbee, a member of a crypto-Amish order called "The Squeamish", who takes over Amy Sedaris’s cheese ball operation. His performances were highly regarded by some critics. Rakoff has portrayed Lance Loud on stage and has appeared in other plays including "David & Jodi & David and Jackie", inspired by the 60’s classic "Bob & Carol & Ted & Alice", alongside Jackie Hoffman, David Ilku and Jodi Lennon and "The Cartells". He also delivered a monologue about being fired in the stage show "Fired!".

Voice work

The Canadian-born Rakoff voiced the part of the US President Thomas Jefferson for the audio book of Jon Stewart's America (The Book): A Citizen’s Guide to Democracy Inaction and provided the voice of Polish-American Leon Czolgosz (the assassin of US President William McKinley) in the audio book version of Sarah Vowell’s Assassination Vacation.

Directing

In 1994, Rakoff directed Stitches, by David and Amy Sedaris. His direction was described as "clearly focused" by The New York Times and "brisk" by Newsday. He also directed Jail Babes starring The Duelling Bankheads (David Ilku and Clark Render) at La Mama, E.T.C. in 1996, and Mike Albo's one-man show, Spray, at P.S. 122 in New York.

General

• David Rakoff’s biography on his agent’s site
• David Rakoff’s IMDb page
• David Rakoff’s filmography from the New York Times
• David Rakoff’s favourite books
• David Rakoff’s favourite essays

Videos made with Dave Hill

• David Rakoff and Dave Hill go on a book tour
• Law and Order BFD: Special investigation by David Rakoff and Dave Hill
• Going up with Dave Hill: Dave Hill, David Rakoff exiled by security (New York Magazine)
• Stomp!* with Dave Hill, David Rakoff and Martha Plimpton
• The sheriff of Prospect Park with Dave Hill and David Rakoff
• Little Michael Jackson and me: Episode 3: we can work it out

Other videos

• David Rakoff on cultural excess Pop tech! 2008
• David Rakoff Interview with MSVLive.com
• What’s so funny about America? Appearance of David Rakoff with David Sedaris and Don Watson at Melbourne Writers’ Festival 2008
• David Rakoff and Martha Plimpton using a soda-making machine, the best thing he ever bought
• Wasp Cove, opening credits sequence

Television appearances

• Appearance on Australian TV’s 9 am with David and Kim: August 2008 (search for “Rakoff”)
• Appearance on Late Show with David Letterman: November 1, 2006
• Appearance on The Daily Show with Jon Stewart: October 5, 2006
• Appearance on The Daily Show with Jon Stewart: October 3, 2005
• Appearance on The Daily Show with Jon Stewart: August 13, 2001

Non-fiction essays and articles

• "My first New York" (New York Magazine, 29 March, 2010)
• "All the time we have: When your therapist dies, well, how does that make you feel?" (Guilt & pleasure)
• "Pardon me: my childhood bullying and an attempt to atone for it" (Tablet, September 23, 2009)
• "Why ‘Bruno’ is bad for the gays" (Salon, July 9, 2009)
• "Our True North" (New York Times, July 1, 2009)
• "Not a pet person" (O Magazine, May 12, 2009)
• "Utah and the insane optimism of westward expansion" (Slate, September 10, 2008)
• "The worst gay job in America" (Newmatilda.com, August 22, 2008)
• "Walk This Way" (New York Times, August 16, 2008)
• "The Future Knocks Again" (New York Times, July 10, 2008)
• "Places and prices: Canadian Maritimes" (Conde Nast Traveller, March 2008)
• "Northern Composure" (Conde Nast Traveller, March 2008)
• "Love it or leave it, book excerpt" (Newsweek, January 20, 2008)
• "Oh, the trouble I’ve Heard" (Guilt & Pleasure, Issue 5, Summer 2007)
• "A Basket Case in North Carolina" (New York Times, May 20, 2007)
• "Annie Hall" (Five Dials, No 3, 2007)
• King of the Forest (Tablet, December 6, 2006)
• "Streets of Sorrow" (Conde Nast Traveller, November 2006)
• "Shrimp" (Richard Hugo House, October 14, 2006)
• "75 Years: Voice and views: ‘Reminders of the divine’" (New York Times, April 23, 2006)
• "Whatsizface: two Beverly Hills plastic surgeons showed me the promise of a perfect face" (Salon, November 29, 2005)
• "He’s Not Dead Yet" (Outside, July 2005)
• "Stations of the Crawl" (New York Magazine, May 21, 2005)
• "2003: The 3rd annual Year in Ideas; Makeup for men" (New York Times, December 14, 2003)
• "Skin Crawling: David Rakoff faces off with the plastic surgeons of Beverly Hills" (GQ, October 2004)
• "Hiroshima Bomber and Victims: This Is Your (Puppet’s) Life" (New York Times, January 11, 2004)
• "The Lives They Lived : Celebrity Bushman" (New York Times, December 28, 2003)
• "Stores: the economy of cool" (New York Times, May 18, 2003)
• "Places and prices: British Columbia Lodges" (Conde Nast Traveller, March 2003)
• "Evergreen Safari" (Conde Nast Traveller, March 2003)
• "Fu Fighters" (Outside, 2003)
• "The Lives They lived: The Debutante’s Staying-In Party" (New York Times, December 29, 2002)
• "The Year in Ideas: Gizmo-finding gizmo" (December 15, 2002)
• "What scares me: (fear of) being buried alive" (Outside, September 2002)
• "Edie Falco’s endless summer" (New York Times, July 7, 2002)
• "The Year in Ideas: Unexamined Life is Worth Living, The" (December 15, 2002, New York Times)
• "An Interview with The Artist: Eric Fischl"(New York Art World, October 27, 2002)
• "The Year in Ideas: A to Z; focus on the negative" (New York Times, December 9, 2001)
• "The Lives They Lived: 01-07-01: Mark R. Hughes, b. 1956; Death Be Not a Punch Line" (New York Times, January 7, 2001)
• "Barbra’s farewell: A city Verklempt" (Observer, October 1, 2000)
• "I, Nature Boy" (Outside, October 2000)
• "The love that dare not squeak its name: Even as a child I suspected I had something special in common with Stuart Little" (Salon, December 21, 1999) Letter to the editor including a measured response to article (Salon, December 21, 1999)
• "The Writer’s Life: A titan of American letters reflects on his timeless art and the sacrifices it exacts" (Salon, November 9, 1999)
• "Lives: Pandora’s idiot box" (New York Times, July 18, 1999)
• "Glorious Gwyneth" (Salon, April 2, 1999)
• "Deep Thought Oprah, That Carabiner Won’t Hold: Paul Stoltz explains by anybody who isn’t a climber is, well, a loser" (Outside, October 1998)
• "Smells Like Tina Spirit" (New York Magazine, October 12, 1998) * "Online diary" (Slate, May 1998)
• "The Critic’s Eye: A Rise Is a Rise Is a Rise" (New York Magazine, April 13, 1998)
• "The wizards of Id" (Salon, June 13, 1997)
• "A former smoker cheers" (New York Times, April 14, 1995)
• "Up. Down. Up. Down. Up. Down. Up. Down. And Then, By Golly, Up Again" (Outside, March 1998)
• "About men: extraordinary alien" (New York Times, October 9, 1994)

Fiction or satire

• "If Gore had won, an alternate oral history of the last decade" (Newsweek, 2010)
• "Other Newfound Bloomberg FANS" (New York Magazine, November 20, 2005)
• "KringleTech Worldwide Restates Earnings Existence of CEO Still in Doubt as Key Holiday Season Approaches" (Money, CNN, December 1, 2002.
• "Relations: Friends and allies across the divide; Merce Cunningham and Nam June Paik" (New York Times, July 16, 2000)
• "Lives; 'Sometimes you get wistful about actually looking like a person'" (New York Times, January 9, 2000)
• "The Lives They Lived: Questions for James B Maas; Candid Classroom" (New York Times, January 2, 2000)
• "The few. The brave. The capitalists" (Outside, June 1999)
• "If the starr report were a novel, work of history, subject of moral philosophy, psychiatric case study or soap opera, WHAT KIND OF FOOTPRINT WOULD IT LEAVE?" (Outside, June 1999)
• "The Annotated Manifesto of Troop 109: The skills a boy acquires in scouting last a lifetime, without parole" (Outside, November 1998)
• "Poet....Lover....Omnivore....Friend: A consideration of Bart the Bear, from those whose lives he’s touched" (Outside, August 1998)
• "Chekhov, Marx and synergy" (Salon, 1998)
• "The 1998 Outside Prognosticator" (Outside, January 1998)
• "El Nino has a Headache" (Outside, December 1997)
• "Media circus: What's up, Dike?" (Salon, August 12, 1997)
• "The kiss-up: a writer and his agent discuss literary strategy" (Salon, March 3, 1997)
• "The Making of Fatal Death" (Outside, March 2000)

Blog entries

The following entries in a blog about watching 28 Woody Allen movies in 28 days appeared in Tablet:

• "Deconstructing Harry and Crimes and MisdemeanorsThat’s All, Folks!" (January 13, 2007)
• "Interiors and Stardust Memories" (January 10, 2007)* "Zelig and The Front" (January 10, 2007)
• "Take The Money and Run and What’s Up, Tiger Lily?" (January 8, 2007)
• "A Midsummer Night’s Sex Comedy" and Another Woman (January 4, 2007)
• "Manhattan" (January 7, 2007)
• "Husbands and Wives and Hannah and Her Sisters" (January 3, 2007)
• "Bananas and Sleeper" (January 1, 2007)
• "Wild Man Blues and (not) Sweet and Lowdown" (January 2, 2007)
• "Radio Days and Broadway Danny Rose" (December 31, 2006)
• "Bullets Over Broadway and Everyone Says I Love You" (December 28, 2006)
• "Love and Death and Everything You Always Wanted to Know About Sex (But Were Afraid To Ask)" (December 27, 2006)
• "Mighty Aphrodite and Manhattan Murder Mystery" (December 26, 2006)
• "Play It Again, Sam and The Purple Rose of Cairo" (December 24, 2006) ()
• "Annie Hall" (December 22, 2006)
• "I’ve been trying to remember, was it the Sorrow and the Pity?" (December 21, 2006)

Radio work

The following episodes of This American Life feature work by David Rakoff:

• 389: Frenemies — Speak now or forever hold your peace (September 11, 2009): Rakoff demonstrates...in rhyme...how to make a wedding toast for people you never wanted to see married in the first place
• 386: Fine print — Occupancy may be revoked(July 24, 2009): Rakoff drafts a legal agreement between a mother and son
• 354: Mistakes were made — You’re Willing to Sacrifice Our Love (April 11, 2009): Rakoff provides a re-interpretation of the famous William Carlos Williams poem
• 345: Ties that bind — Fred and Barney (December 14, 2007): Rakoff as Barney’s friend Fred
• 343: Poultry slam 07 — The Meaning of a Bird(November 23, 2007): Rakoff explains how his life was changed — in a single evening — in a room of 5000 chickens
• 328: What I learned from television — 29 (May 2, 2008): Rakoff attempts to watch 29 hours of television in one week
• 305: The ‘This American Life’ Holiday Spectacular — Twas the Morning After (December 22, 2006): A Christmas poem by David Rakoff
• 259: Promised land — Life in the Fast Lane (September 30, 2005): Rakoff fasts
• 248: Like it or not — Prologue (August 12, 2005): Rakoff on an inevitable experience as a strange, round limbed, feminine little kid
• 208: Office politics — Sheetcakes in the Conference Room, Whiskey After Dark(March 15, 2002): Rakoff discusses work celebrations
• 194: Before and After — Watching from the River's Edge(September 21, 2001): Rakoff discusses another disaster
• 192: Meet the pros — Martha, My Dear (September 14, 2007): Rakoff goes to Martha Stewart‘s
• 169: Pursuit of Happiness — One Man's Treasure Is Another Man's Trash (September 29, 2000): Rakoff goes on a scavenger hunt
• 156: What Remains — I Used To Bank Here But That Was Long, Long Ago (March 31, 2000): Rakoff tries to track down his semen
• 146: Urban Nature — Interpretation of Dreams (December 10, 1999): Rakoff looks for hidden people in Iceland
• 140: Family Business — What's a Grecian Urn? (September 23, 1999): Rakoff on a Greek-owned icecream parlour
• 124: Welcome to America — What Do Arnold Schwarzenegger and Sigmund Freud Have In Common? (July 5, 2002): Rakoff reports on importing Austrian teachers
• 118: What You Lookin’ At? — Climb every mountain (March 19, 1999): Rakoff climbs a mountain in plastic shoes on Christmas day and everyone is looking at him
• 65: Who’s Canadian? — White like me (May 30, 1997): Rakoff on how he tried to pass as an American
• 47: Christmas and Commerce (December 20, 1996): Rakoff’s Christmas Freud

Rakoff also appeared on the following radio program:

• Contribution to "Tales of Terror" Weekend America (October 25, 2008)* Wire tap CBC RadioOne Season 6, Into America and Season 5: Buzz pick up the phone: the best of season 5

Other media

• David Rakoff on Disney’s New Dream Home for the New York Times
• Post-it note reading series — Seasons
• Animated excerpt from the book Don’t Get Too Comfortable