MY TOP 5 LONGREADS OF ALL TIME

This is certainly not a comprehensive list of great essays, but these are the ones I've remembered years after I read them.
  1. 1.
    "Letting Go" by Atul Gawande
    On how we die and the limits of medicine. One of the saddest stories I've ever read; I was bawling. http://www.newyorker.com/magazine/2010/08/02/letting-go-2
  2. 2.
    "Consider the Lobster" by David Foster Wallace
  3. 3.
    "The American Male at Age 10" by Susan Orlean
    When Susan Orlean was asked to profile Macaulay Culkin, she agreed, as long as she could interview a random 10-year-old kid instead. The result is so delightful. http://m.learning.hccs.edu/faculty/scotty.moore/anth2351/anth-2301-summer-readings/the-american-male-at-age-10
  4. 4.
    "The Rapist Says He's Sorry" by Tom Junod
    The story of a supposedly reformed serial rapist who is about to get out of jail. Brilliantly structured, beautifully written. http://gangrey.com/?p=1151
  5. 5.
    "The Well-Hung Boy Next Door" by Wells Tower
    This is not exactly a pleasant story. In fact, one scene toward the end may be one of the most traumatizing things I've ever read. But it's a fascinating look at what it's really like to be a male porn star, and I have never forgotten it. http://www.gq.com/story/james-deen-porn-star-gq-june-2012-interview