Revisiting David Foster Wallace’s Boston

The novelist David Foster Wallace has resurfaced on film and in our radio archive, so we’re revisiting one of our favorite shows of the year this week: “Infinite Boston,” a tribute to Wallace’s magnum opus Infinite Jest and its real-life roots in Cambridge and Brighton.

The actor Jason Segel will don the famous bandana on the big screen later this year for The End of the Tour. A few weeks ago Sotheby’s sold off a small lot of personal and private letters Wallace wrote to his friend J.T. Jackson during the worst years of his life. And, burying the lead, we dug up the famous Connection interview with Wallace from the spring of 1996, when he was back in town on a book tour for Infinite Jest. Wallace talked with Chris about the book, Boston AA meetings, the lonely and lost Generation X, and his place in U.S. literature.

Our show this winter featured an audio tour of Wallace’s Boston with the local raconteur and Wallace expert Bill Lattanzi, interviews with his biographer D. T. Max, the editor and writer Sven Birkerts, and a conversation with Lattanzi and Deb Larson, Wallace’s friend and mentor at the halfway house where Wallace lived during those heartbreaking Boston years.


A sad, sweet postcard from Wallace to J.T. Jackson from 1990. The front showed “A Foggy Day In Boston, Massachusetts”.

Thanks again to Nick Maniatis, founder of Howling Fantods, who sent us an eloquent audio love letter to DFW (mp3), and Christopher Boucher, the writer and editor teaching his students to walk Infinite Jest at B.C.

Image credit: Richard Burrbridge/Rolling Stone.

Reading List
An Interval
David Foster Wallace
an excerpt from Infinite Jest that was published in The New Yorker in January 1995, including a description of Ennet House director Pat Montesian, the character based on our guest, Deb Larson-Venable
Deb's Story
Deb Larson-Venable
a partial autobiography by Deb Larson-Venable herself, on the Granada House website, and "An Ex-Resident's Story", an anonymous article (credited to Wallace) about Granada House, the Brighton halfway house that became Ennet House in Infinite Jest
The Unfinished
D.T. Max
the article by D.T. Max about Wallace's biography and career that spawned his book,  Every Love Story is a Ghost Story
The Map and the Territory
Adam Kelly
an excellent article by Adam Kelly on Bill Lattanzi's Infinite Jest tour
Infinite Boston
William Beutler
designer William Beutler's amazing record of his own whirlwind tour of Wallace's Boston

Related Content

  • Kunal

    For more original David Foster Wallace content we’re going to release over the next week, please subscribe to our podcast at

  • Joe Allonby

    My first reaction to IJ was the shock of recognition. I had to have run across this guy. I knew these places and people. The WMBR djs. The junkies and drunkards.The crocodiles. The streets of Allston and Brighton. I even worked on Rugg Rd where the campers were parked. I knew that I had to have crossed paths with this guy sometime. He was describing my world in a way that was both realistic and surreal or fantastic. It was like waking up to find that I was a character in Gravity’s Rainbow.

  • peta

    Oh my goodness, why did you give so much (dead) airtime to Deb Larsen? God she just drained the energy out of the program in the last 20 minutes, causing the show to go nowhere.. ughh..

    • Kunal

      I thought that was the best part of the interview, actually! Did you know she’s the basis for Pat Montesian in “Infinite Jest”?

  • Cambridge Forecast

    Two “Flashlights” on Wallace as described by ROS panel: Prof. Sean Kelly and Walker Percy:
    Prof. Sean Kelly of Harvard talked about his book “All Things Shining” a few years ago at the Harvard Bookstore in Harvard Square
    and uses David Foster Wallace’s phrase, “stomach-level sadness” (see below) as a kind of pole star or lighthouse for the whole discussion. The book “All Things Shining” has an extensive discussion of David Foster Wallace who gives Prof. Kelly a kind of “intuitive GPS” for the whole.

    Of Infinite Jest, Wallace said in a 1996 interview with the online magazine Salon: “I wanted to do something sad. I’d done some funny stuff and some heavy, intellectual stuff, but I’d never done anything sad… The other banality would be: I wanted to do something real American, about what it’s like to live in America around the millennium… There’s something particularly sad about it, something that doesn’t have very much to do with physical circumstances, or the economy, or any of the stuff that gets talked about in the news. It’s more like a stomach-level sadness. I see it in myself and my friends in different ways. It manifests itself as a kind of lostness. Whether it’s unique to our generation I really don’t know.”

    After dropping out of the Harvard Philosophy Department PHD program, Wallace enrolled in creative writing at University of Arizona.

    His first novel, The Broom of the System told the story of Lenore Stonecipher Beadsman, and her difficulties with Wittgenstein, an unsatisfactory boyfriend and a foul-mouthed cockatiel.

    While DFW explored Wittgenstein, another “lostness” observer, Walker Percy, studied Heidegger and Kierkegaard and might favorable be “clustered” with DFW, for example:

    “You live in a deranged age – more deranged than usual, because despite great scientific and technological advances, man has not the faintest idea of who he is or what he is doing.”

    ― Walker Percy, Lost in the Cosmos:The Last Self-Help Book

    Why is it that of all the billions and billions of strange objects in the Cosmos – novas, quasars, pulsars, black holes – you are beyond doubt the strangest

    Why is it possible to learn more in ten minutes about the Crab Nebula in
    Taurus, which is 6,000 light-years away, than you presently know about
    yourself, even though you’ve been stuck with yourself all your life”

    ― Walker Percy, Lost in the Cosmos: The Last Self-Help Book

    “Lost in the Cosmos: The Last Self-Help Book” is a mock self-help book and social satire on the American value of autonomy by Walker Percy. It was published in 1983 by Farrar Straus & Giroux.
    DFW’s “Infinite Jest” and Walker Percy’s book might be twinned to the advantage of both. Wallace’s “stomach-level sadness” might fit in comfortably with Walker Percy “lostness”.
    Richard Melson