Days Of Awe(some) Books: A High Holiday Reading List

David Foster Wallace, Moby-Dick, and of course some Kafka: This ain’t your typical Rosh Hashanah to Yom Kippur reading list. Read More

By / September 26, 2011

The High Holidays rarely pass through us easily. Whether we embrace them or not, they take their toll. For some, aloof from the exigencies of judgment and repentance, they feel lost or astray from the community, from their tradition and history during these times, uncertain as to their desire to even make these days relevant. Others, awhirl in throes of doubt, do not understand how to relate to these days of awe as a skeptic, with a religious foundation made precarious by the gnawing of uncertainty. While others, hoping to attach themselves to the cosmic drama of the day, feel alienated by the archaic tone and content of the services. These books, I hope, will arouse the reader to the possibility of the divine, of self-transcendence, of the relevance of religion in our time, no matter the path taken.

I believe each book, in a unique manner evokes questions we all must ask, questions we thought we put to bed in the days of our youth, but questions that demand a more mature struggle than we give them credit for. This list, by no means comprehensive, represents an array of books, short stories and essays that speak to different personalities we all might harbor within us: the philosopher, the poet, the mystic, the skeptic, the rebel, the lost, the bored, the tired, and the hopeful. These works, largely centered on sensing at least the possibility of transcendence and divinity in the world, also contain an underlying abrasive and rebellious streak. What unites this list is its ability to make us think on a different level than our normal everyday patterns of thought.


1. To the Lighthouse by Virgina Woolf – To the Lighthouse, possibly more than other book, manages to capture the unfathomable beauty of one transient tick of the clock, while at the same time illuminating the deep wound and sadness of the mere ethereal nature of a human being. Woolf deftly weaves the large questions through the tiniest, most encapsulating details of life. Besides a blissful read, To the Lighthouse confronts mortality, good and evil, and the meaning of life without the preachy nature or sanctimoniousness of a self-help book.

2. City of God – I found this book by accident. I stayed away from E.L. Doctorow because I thought Ragtime was a piece of show tunes genre fiction instead of the dazzling piece of literature that lies before us. I first fell in love with Doctorow in his relatively unknown City of God. In this initially baffling work, Doctorow uses the mystery of a stolen Church cross that ends up on a uber-liberal synagogue’s roof to enter into the mysteries of the world. Mixing together philosophy, theology, absurdity, humor, cosmology, and good ol’ love, Doctorow provides the sweep of experience in this fascinating take on a mystery novel.

3. 36 Arguments for the Existence of God: A Fiction by Rebecca Newberger Goldstein– Despite the joke or jab in the title, Goldstein’s highly praised book captures so much of the religious experience today: the hopes we bring towards it, the intellectual assumptions we dismiss, the allure of atheism, and the absurdities in fanaticism of all types, even in the world of academia. In the end, the complex relationships ground the book in human beauty that allows us to realize the pervasive struggles with religious feelings of all kinds.

4. A Foreskin’s Lament, Beware of God by Shalom Auslander – Let’s face it, some of us relate to God and religion, if at all, solely through anger and resentment. To experience someone else’s deep and visceral anger and resentment, to either connect to it, or feel lightened in your own religious trauma, or to glimpse the complex relationship between family dynamics and religious views, then enjoy the seering anger of Foreskin’s Lament as Auslander gnashes his teeth at his family and all things holy. Or enjoy his cleverer and more creative book of short stories Beware of God, in which he throws a quick 14 stories at you that read easily, but hit hard, fast, and stay with you likes the cherished bruises of war.


1. The Varieties of Religious Experience by William James- Basically the touchstone for the academic field of psychology of religion and a watershed book in the field of philosophy of religion as well. James writes with the clarity of a journalist and the eloquence of a poet as he documents the various manifestations, types, and stages of religious life. He makes a compelling argument for the relevance of religion that still hits hard for those willing to wade through this tome. For those hoping for a shortened version, the chapters on the healthy-minded and sick soul stand out, as do the chapters on conversion (see previous link.) For a type of updated version, see one of the greatest living religious philosophers, Charles Taylor, riff on the Varieties in his considerably shorter, Varieties of Religious Today: William James Revisited.

2. The Screwtape Letters – An easy choice. Here we see C.S. Lewis at the heights of his strengths. In this epistolary account between a senior demon, Screwtape, and his minion, Wormwood, regarding their attempts to entice a human into sin, Lewis melds his talents at populist religious edification with a nuanced understanding of the human being to create something more than apologetics that characterizes much of his work. Through this story he creates a deceptively in depth exploration of sin, personal degeneration and redemption.

3. Days of Awe – edited with an introduction and comments by Shai Agnon –  The essential collection of Jewish sources on the high holidays would alone make this book a staple of any similar type of list, but the foreword from Arthur Green and the introduction from Judah Goldin shine through with brilliance and perceptivity. Goldin’s introduction might stand as one of the best modern sermons ever written for the high holidays.

4. Sacred Attunement –Michael Fishbane- This book made a big splash in the academic world a couple years back as Michael Fishbane, a Biblical scholar, wrote a postmodern theological tract that attempts to stake a claim for the relevance of theology in secular age. Much of the book focuses on the act of focusing, or attunement, to the divine around us whether through the bible, literature, beauty, music, or relationships. I can’t say he succeeds fully, but watching him try, with his considerable library of a mind, and occasional poetic brilliance is well worth the effort of the density of this small book. Recommended for the academically inclined.

5.Poetic Theologians (Heschel, Tillich, Kook) – These poetic theologians take a more experiential approach to faith and belief, relying on evoking a sense of awe and wonder at the mystery of existence instead of using their considerable intellects to create precarious towers of proof. If this aspect doesn’t interest you, sometimes, even if I cannot connect to their passion personally, just reading an account of such passionate faith, of such utopian belief provides an erection of the heart, as some would call it. Abraham J. Heschel Man’s Quest for God explores the meaning and necessity of prayer in his style of lyrical prose that belies the depth of his philosophical acumen. Similarly, read either his Man’s Search for God, or the companion God’s Search for Man. Expect to take breaks while you sit with his weighty ideas. For a more universal viewpoint see Paul Tillich’s Courage to Be or Dynamics of Faith. Finally, for the last of the poetic theologians in this group, try to wade through the brilliance of Abraham Isaac Kook’s Lights of Repentance for a cryptic, but inspiring vision of universal perfection.


1. Yehuda Amichai: always moving, always abrasive. Some of his poems deal specifically with themes of the High Holidays (See his On the Eve of Rosh Hashanah, Yom Kippur) regardless, Jewish themes permeate his work in a manner that always forces the reader to not only think, but feel anew.

2. Emily Dickinson – How can we begin to speak about poetry and facing our mortality without bringing in the Goddess of Poetry, Emily Dickinson, whose cryptic verses trigger something so deep we often barely perceive its effect until a few days later when she knocks us to the ground? For those who, like me, find it hard to crack Dickinson’s codes, read an explication by one of our greatest teachers of poetry, Helen Vendler, in her new book, Dickinson: Selected Poems and Commentaries.

3. Leonard Cohen – Also, for your consideration, see the Everyman’s Library collected poems and songs of the venerable Leonard Cohen. Though we put a moratorium on covering Hallelujah, the rest of his oeuvre deserves our attention.  Cohen, a hard to pin down poet: part mystic, part skeptic, part sensualist, would make the list if only for his modernized version of Netaneh Tokef in his song Who by Fire, with the achingly beautiful and mysterious refrain of, “Who shall I say is calling.”

Essays, Short Stories, and smaller works.

1. The Brothers Karamazov – Some of us like to jump around from text to text so here’s a smattering of choices from all over the literary globe. In regards to some classics, the conversation between Alyosha and Ivan Karamazov in the fifth book, from the third to the fifth chapter in, The Brothers Karamazov remains one of the best dramatizations of the questions of theodicy and God’s existence in the history of literature. It reads like a hammer of righteous indignation. It’s ferocious in all the right ways.

2. Moby Dick –  On a different note, seeing as we read the book of Jonah on Yom Kippur, read Melville’s take on it found in the preacher’s sermon in Moby Dick, in the chapter aptly entitled the Sermon: scathing, satirical, and piercing.

3. The Death of Ivan Ilych – For a classic in the literature of religious transformation, few works compare to the adroit skill and insight of Tolstoy’s The Death of Ivan Ilych.

4. The Writings of an Ethical Life –by Peter Singer – For those more inclined to connect through social justice, read anything and everything by Peter Singer. Particularly, if you feel caught up in the materialism of this American lifestyle, or if you simply want to get a sense of perspective on our privileged lives, read his early essay Famine, Affluence, and Morality, and his more contemporary How Much Should a Billionaire Give and how Much Should You? For a larger perspective on the place of social justice and our sense of meaning in life, read his chapter A Meaningful Life.

5. David Foster Wallace – For those of us who find the remnants of religion in the cathedral of stadiums, read David Foster Wallace’s Roger Federer as Religious Experience. If this whets your appetite for more of this author’s incisive ability to capture what it feels like to be a human these days, then move on to his graduation speech, but please, don’t stop there. Either read some of his essays, especially his manifesto on the corrosiveness of irony and cynicism on our humanity entitled E Unibus Pluram, or the deeply sad, engaging, and wrenching short story, Good Old Neon in his book Oblivion.

Longer Non-Fiction

1. Franz Kafka – Zurau Aphorisms, or the Octavo Notebooks –. An offering from one of our greatest prophets of uncertainty, these baffling, posthumously published aphorisms and quasi theological notes, will give you enough to think about for a lifetime, and also for a long couple of days. Not for those easily frustrated. Like a good wine, you need to let them breathe for their full effect. Here’s a taste:

A man cannot live without a steady faith in something indestructible within him, though both the faith and the indestructible thing may remain permanently concealed from him. One of the forms of this concealment is the belief in a personal god
And just one more:
Sexual love deceives us as to heavenly love; were it alone, it would not be able to do so, but containing within itself, unknowingly, a germ of heavenly love, it can.

For those feeling lost in the world, and if you’ve never got around to Kafka’s The Trial then set aside this time to do so. Or if you find yourself pressed for time read his gorgeously frustrating short story Before the Law. Kafka rarely disappoints. (For a strange reading of this story by Orson Welles see here.)

2. Annie Dillard – For the Time Being, A Pilgrim at Tinder Creek –Though more famous for her Pulitzer Prize winning, A Pilgrim at Tinder Creek, her non-fiction work that explores God, evil, nature, and meaning, I find Dillard more playful and expansive in her later spiritual exploration For the Time Being. Here, America’s most probing spiritual writer creates a kind of searching narrative that ranges from clay warriors unearthed in China, to the beauty and mysteries of Hasidism, along with a horrifying glimpse into the endless possibilities of human deformities, all which provokes, but rarely answers, some seriously perplexing, mysterious, and wonderful questions.