David Foster Wallace combined his phenomenal intelligence and gift for writing with a high level of self-awareness, and a deep awareness of the brutality and enormity of the world. He had an almost omnipotent ability to understand and communicate about what it means to be human in his iconic books.

Like most highly sensitive people he felt overwhelmed by the world and almost unbearably lonely to the point of deep sadness (I can relate); but he also communicated ingenious levels of insight in his books that overshadows almost all other writers. It seemed that he wrote as much for his own sanity and health as he did for his public. He was a man and a writer not from his time (the 80’s and 90’s) but not really from any time, he was timeless. Foster-Wallace went beyond the comfort zone of people, content to sleep-walk through their lives. His writing and his sense of hopelessness and irony were like a canary in the coalmine, a message and a warning about for how fucked up the world will become and yet how perilously precious it is as well.

Listen to this podcast about his life and work, recorded shortly after his tragic death:

The biopic of Foster-Wallace’s life, End of the Tour charts the recording of a five day interview between Rolling Stone reporter David Lipsky and acclaimed novelist David Foster Wallace, which took place right after the 1996 publication of Wallace’s groundbreaking epic novel, ‘Infinite Jest.’  It’s brilliantly acted and infused with a deep sense of sadness and loneliness which would have no doubt punctuated his real life. Here’s the trailer

Here’s some philosophical insights from him

On reading

“I do things like get in a taxi and say, “The library, and step on it.”
― David Foster Wallace, Infinite Jest

“The truth will set you free. But not until it is finished with you.”
― David Foster Wallace, Infinite Jest

“Good fiction’s job is to comfort the disturbed and disturb the comfortable.”
― David Foster Wallace

On being caring

“The really important kind of freedom involves attention, and awareness, and discipline, and effort, and being able truly to care about other people and to sacrifice for them, over and over, in myriad petty little unsexy ways, every day.”
― David Foster Wallace, This Is Water: Some Thoughts, Delivered on a Significant Occasion, about Living a Compassionate Life

On being yourself

“You will become way less concerned with what other people think of you when you realize how seldom they do.”
― David Foster Wallace, Infinite Jest

On loneliness

“Fiction is one of the few experiences where loneliness can be both confronted and relieved. Drugs, movies where stuff blows up, loud parties — all these chase away loneliness by making me forget my name’s Dave and I live in a one-by-one box of bone no other party can penetrate or know. Fiction, poetry, music, really deep serious sex, and, in various ways, religion — these are the places (for me) where loneliness is countenanced, stared down, transfigured, treated.”
― David Foster Wallace

“It’s weird to feel like you miss someone you’re not even sure you know.”
― David Foster Wallace, Infinite Jest

“Lonely people tend, rather, to be lonely because they decline to bear the psychic costs of being around other humans. They are allergic to people. People affect them too strongly.”
― David Foster Wallace, A Supposedly Fun Thing I’ll Never Do Again: Essays and Arguments

“Everybody is identical in their secret unspoken belief that way deep down they are different from everyone else.”
― David Foster Wallace, Infinite Jest

On being human

Fiction’s about what it is to be a fucking human being.”
― David Foster Wallace

“That sometimes human beings have to just sit in one place and, like, hurt. That you will become way less concerned with what other people think of you when you realize how seldom they do. That there is such a thing as raw, unalloyed, agendaless kindness. That it is possible to fall asleep during an anxiety attack. That concentrating on anything is very hard work.”
― David Foster Wallace, Infinite Jest

On thinking

“Learning how to think” really means learning how to exercise some control over how and what you think.
It means being conscious and aware enough to choose what you pay attention to and to choose how you construct meaning from experience.
Because if you cannot or will not exercise this kind of choice in adult life, you will be totally hosed.”
― David Foster Wallace, This Is Water: Some Thoughts, Delivered on a Significant Occasion, about Living a Compassionate Life.