Matt asked:

I'm interested in reading DFW after hearing a lot about Infinite Jest and listening to a lot of interviews with him. However I'm not quite in the mood to tackle a 1000 page goliath of book (that IJ is supposedly meant to be) right now so I was considering buying Oblivion. What do any DFW fans think is the best place to start with his work?

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Kellan Marvel This is a tough one. DFW wrote some outstanding magazine articles, which is where I started with his work. His fiction is very, very different (and much more difficult to get through) than his nonfiction. I'd recommend starting with some of his shorter stories (here's a link to his publications in Harper's: ) before diving into his novels. DFW is, hands down, my favorite author to date so I highly recommend reading some of his stuff. Personally, one of my favorite articles he wrote is called "A Supposedly Fun Thing I'll Never Do Again" and it follows his trip on a cruise line (sometimes titled as "Shipping Out").
Malky "Good Old Neon" in Oblivion turned me into a DFW junkie.
Kathleen Consider the Lobster.
David fwiw, Oblivion was where I started. After reading most of his oeuvre, including Infinite Jest, it remains my favorite DFW book.
Sal Very late to this response, but I thought I'd respond for anyone still following this conversation or considering reading some DFW. My recommendation is to start with his non-fiction--Consider The Lobster or A Supposedly Fun Thing... I think that's where he did some of his best, most accessible writing. DFW's fiction is very dense, often touching on a variety of subjects (like most things he writes) with a very intelligent hand.

The Broom of the System is very good, and, while it's great as a work of fiction, it's even better if you have a little understanding of the philosophies that influenced the work. His fiction is similarly very good, but it's also dense. It's unlikely to be like anything you've read before. When you complete a DFW work, you feel accomplished.

Nonfiction ---> Short stories ---> Novels seems to be one way to go, as it's sort of like a gradual immersion into his style and work.
Sam Mccallum There was a book which put forward essays first (A Supposedly Fun Thing I'll Never Do Again, Consider The Lobster, This Is Water) then short stories (Girl With Curious Hair, Brief Interviews With Hideous Men, Oblivion) and finally the novels starting with Infinite Jest. I've been doing this and it's been really enjoyable for the most part (Westward The Course Of Empire Takes Its Way was a slog) so I'd recommend that.
Blake Oblivion is a great place to start. Or his first novel, The Broom of the System.
Debra Wasyliw The short stories “Good Old Neon” and “The Suffering Channel” from Oblivion.

The short story "Little Expressionless Animals" from The Girl with Curious Hair.
David Robson 'Oblivion' is a good place to start. My DFW introduction, however, was 'Brief Interviews with Hideous Men', and while I found it pretty hit-or-miss at the time, the selections are shorter and offer more stylistic variation.
Abram Martinez I think that his most accessible work is The Girl with Curious Hair. However, all of his books fall massively short of Infinite Jest. It seemed like a mountain when I first started, but it becomes something accomplishable once you get into it and the book starts impacting you. Good Luck on any DFW that you read. He is definitely a challenging writer but by far my favorite.
Hillary Powers I would definitely start with Brief Interviews w/ Hideous Men. IJ is really hard to get through, and Oblivion can be similarly challenging. Brief Interviews is digestible while still being a stellar read.
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