Best Books of Letters: 30 Collections of Famous Letters to Live By (2020)


Thursday, 7:04 AM
November 7, 2019

Dear friend,

It struck me recently that I’m in the business of letter writing.

And since I’d like to write you the best letters I possibly can, I decided it’s a skill I should probably work at.

And since the best way to master any skill is to mimic the masters, I decided to put together this list of the 30 the best collections of letters ever written.

As usual, I’ve organised my long-list (of over 100 collections) to surface what’s survived, what’s widely read and what’s wonderful (though this is a bit trickier with letter collections than other genres since the original letters often predate any attempt to organise them).

If you know of any obvious candidates that deserve to appear on this list, I’d love to know. Just hit reply and send me your suggestion.

And until then, I hope you enjoy some of the wit, wisdom and intimacy that makes this genre one of my absolute favourites.

Have a wonderful rest of your week, be your best self and go well,

Arthur “I Don’t Know How To Write Love Letters” Worsley
07:24 AM

P.s., Not sure what to read first? I’d start with #1, #3 and #14.

The 30 Best Collections of Letters Ever Written

  1. Letters from a Stoic (-49), Seneca
    256 pages. Rated 4.3 over 14,800 reviews on Goodreads.
  2. The Screwtape Letters (1942), C.S. Lewis
    223 pages. Rated 4.2 over 279,200 reviews on Goodreads.
  3. Letters to a Young Poet (1929), Rainer Maria Rilke
    80 pages. Rated 4.3 over 39,400 reviews on Goodreads.
  4. The Letters of Vincent van Gogh (1914), Vincent van Gogh
    528 pages. Rated 4.0 over 67,300 reviews on Goodreads.
  5. Letters from Father Christmas (1943), J.R.R. Tolkien
    111 pages. Rated 4.2 over 9,200 reviews on Goodreads.
  6. Letter from the Birmingham Jail (1963), Martin Luther King Jr.
    35 pages. Rated 4.7 over 4,000 reviews on Goodreads.
  7. My Dearest Friend (1840), Abigail Adams
    Letters of Abigail and John Adams
    508 pages. Rated 4.2 over 2,100 reviews on Goodreads.
  8. The Habit of Being (1978), Flannery O’Connor
    Letters of Flannery O’Connor
    640 pages. Rated 4.5 over 1,700 reviews on Goodreads.
  9. Jane Austen’s Letters (1932), Jane Austen
    672 pages. Rated 4.2 over 2,400 reviews on Goodreads.
  10. The Adams-Jefferson Letters (1959), Lester J. Cappon
    The Complete Correspondence Between Thomas Jefferson and Abigail and John Adams
    690 pages. Rated 4.3 over 1,100 reviews on Goodreads.
  11. Tiny Beautiful Things (2012), Cheryl Strayed (Summary)
    Advice on Love and Life from Dear Sugar
    A heart thumpingly raw, vulnerable and powerful collection of letters and advice on the power of love, of forgiveness and of finding growth in the darkest of places – by award-winning writer, Cheryl Strayed.
    304 pages. Rated 4.3 over 50,300 reviews on Goodreads.
  12. The Letters of Vita Sackville-West and Virginia Woolf (1965), Louise DeSalvo
    480 pages. Rated 4.3 over 1,300 reviews on Goodreads.
  13. Letters of John Keats (1954), John Keats
    448 pages. Rated 4.4 over 400 reviews on Goodreads.
  14. Letters from a Self-Made Merchant to His Son (1902), George Horace Lorimer
    364 pages. Rated 4.1 over 1,100 reviews on Goodreads.
  15. The Letters of J.R.R. Tolkien (1981), J.R.R. Tolkien
    502 pages. Rated 4.2 over 5,200 reviews on Goodreads.
  16. Letters Home (1975), Sylvia Plath
    502 pages. Rated 4.2 over 2,600 reviews on Goodreads.
  17. A Literate Passion (1965), Anaïs Nin
    Letters of Anaïs Nin Henry Miller, 1932-1953
    448 pages. Rated 4.2 over 1,900 reviews on Goodreads.
  18. Anne Sexton (1977), Anne Sexton
    A Self-Portrait in Letters
    433 pages. Rated 4.3 over 1,600 reviews on Goodreads.
  19. Letters of Wolfgang Amadeus Mozart (1928), Wolfgang Amadeus Mozart
    320 pages. Rated 4.2 over 200 reviews on Goodreads.
  20. Letter to His Father (1952), Franz Kafka
    127 pages. Rated 3.9 over 13,000 reviews on Goodreads.
  21. The Complete Letters of Oscar Wilde (1962), Oscar Wilde
    1,270 pages. Rated 4.3 over 300 reviews on Goodreads.
  22. The Letters of Virginia Woolf (1975), Virginia Woolf
    Vol. One, 1888-1912
    566 pages. Rated 4.3 over 600 reviews on Goodreads.
  23. Selected Letters (1925), Marcus Tullius Cicero
    288 pages. Rated 4.0 over 600 reviews on Goodreads.
  24. The Bach Reader (1945), Hans T. David
    A Life of Johann Sebastian Bach in Letters and Documents
    474 pages. Rated 4.4 over <100 reviews on Goodreads.
  25. Magick Without Tears (1954), Aleister Crowley
    528 pages. Rated 4.1 over 1,000 reviews on Goodreads.
  26. Letters to Children (1985), C.S. Lewis
    128 pages. Rated 4.2 over 1,900 reviews on Goodreads.
  27. Beethoven (1960), Ludwig van Beethoven
    Letters, Journals and Conversations
    281 pages. Rated 4.4 over <100 reviews on Goodreads.
  28. Letters to a Young Contrarian (2001), Christopher Hitchens
    141 pages. Rated 4.1 over 9,100 reviews on Goodreads.
  29. Lord Byron (1972), Lord Byron
    Selected Letters and Journals
    408 pages. Rated 4.4 over <100 reviews on Goodreads.
  30. Selected Letters III (1971), H.P. Lovecraft
    451 pages. Rated 4.4 over <100 reviews on Goodreads.

II. Best Books Of All Time

These are the overall best books to read (by type).

III. Best Nonfiction Books (A-Z)

These are the best nonfiction books to read (by topic).

IV. Best Fiction Books (A-Z)

These are the best fiction books to read (by genre).

Or, you can read all my book recommendations.
Arthur is a productivity coach and writer who helps top young execs and entrepreneurs be more productive, find more balance and live more meaningfully. Want to know more? Take this 2-minute quiz to discover your Productivity Quotient (PQ) and learn how to get BIG things done. Take the Quiz →
Notify of
Inline Feedbacks
View all comments