Infinite Jest is amazing, but I know that it's difficult to get through and there is nothing worse than not being able to have the DFW conversation with hipsters who are pretending they read it.
  1. Oblivion
    Short stories. This will give you a sense of his fiction. Very easy read. At times very abstract and kind of hard to pin down, ie classic DFW.
  2. A Supposedly Fun Thing I'll Never Do Again
    Either just the essay or the collection of non-fiction named after the essay. Do NOT read the magazine version or any shorter versions. The maximalism of his non-fiction is incredibly important to experience in full. This is also an excellent way for you to feel out his use of on-page mechanics like footnotes/endnotes.
  3. Consider the Lobster
    Either the essay (once again, not the shortened crappy magazine one, the one from his book) or the collection by the same name. This is one of the best moments of DFW's genius. An essay about the Maine Lobster Festival paid for by Gourmet magazine, which eventually finds its way to being one about ethics and cruelty and the nature of pain and eating animals. A perfect moment of DFW's power move (IMHO): respectfully rolling around in complex human issues in casual prose and contexts.