This is Tablet Magazine's 101 Great Jewish Books -- they deliberately avoid saying 'the greatest', and are just listing 101 books they think make up part of "the collective inheritance of the Jewish people as read by Jews like us in America". There are a number of books on the list that I've intended to get around to but never have -- I really want to read the Benjamin-Scholem correspondence, for instance, since I've read a fair amount of Scholem and have two of his books on my shelves -- and there are quite a few others others I've dipped into in one way or another but can't exactly say I've read (e.g., while I've looked at Rashi's commentaries -- on Mishlei, for instance -- I can't imagine just sitting down with them); but the ones I've really read, cover to cover, are in bold.
Appetites
Portnoy’s Complaint, Philip Roth (1969)
The Savage Mind, Claude Lévi-Strauss (1962)
Satan in Goray, Isaac Bashevis Singer (1955)
The Armies of the Night, Norman Mailer (1968)
The Dialectic of Sex, Shulamith Firestone (1970)
The Power Broker, Robert Caro (1974)
Fear of Flying, Erica Jong (1973)
Where the Wild Things Are, Maurice Sendak (1963)
Justine, Lawrence Durrell (1957)
Dr. Ruth’s Guide to Good Sex, Dr. Ruth Westheimer (1983)
What Makes Sammy Run?, Budd Schulberg (1941)
Auto-da-Fé, Elias Canetti (1935)
The Mind-Body Problem, Rebecca Goldstein (1993)
The Passion According to GH, Clarice Lispector (1964)
Authenticity & Experimentation
The Counterlife, Philip Roth (1986)
The Rise of David Levinsky, Abraham Cahan (1917)
The Diary of Anne Frank, Anne Frank (1947)
Call It Sleep, Henry Roth (1934)
Two Concepts of Liberty, Isaiah Berlin (1958)
The Amazing Adventures of Kavalier & Clay, Michael Chabon (2000)
The Memoir of Glückel of Hamelin, Glückel of Hamelin (1700)
Correspondence, Walter Benjamin and Gershom Scholem (1992)
Making It, Norman Podhoretz (1967)
The Adventures of K’Ton Ton, Sadie Rose Weilerstein (1935)
Exodus, Leon Uris (1958)
Altneuland, Theodor Herzl (1902)
The Chosen, Chaim Potok (1967)
In Dreams Begin Responsibilities, Delmore Schwartz (1938)
Really the Blues, Mezz Mezzrow (1946)
Only Yesterday, S.Y. Agnon (1945)
Adventures in the Screen Trade, William Goldman (1983)
Marjorie Morningstar, Herman Wouk (1955)
Laughing & Complaining
Herzog, Saul Bellow (1964)
The Feminine Mystique, Betty Friedan (1963)
Auto-Emancipation, Leo Pinsker (1882)
Without Feathers, Woody Allen (1975)
Das Kapital, Karl Marx (1867)
Adam Resurrected, Yoram Kaniuk (1971)
The Anxiety of Influence, Harold Bloom (1973)
Ethics, Baruch Spinoza (1677)
Catch-22, Joseph Heller (1961)
Philosophical Investigations, Ludwig Wittgenstein (1953)
Breakdown and Bereavement, Joseph Haim Brenner (1920)
The Street of Crocodiles, Bruno Schulz (1934)
Hungry Hearts, Anzia Yezierska (1920)
The Jew in the World
The Norton Anthology of English Literature, edited by M.H. Abrams (1962)
All-of-a-Kind Family, Sydney Taylor (1951)
Ulysses, James Joyce (1922)
Red Cavalry, Isaac Babel (1920s)
Swann’s Way, Marcel Proust (1913)
Interpretation of Dreams, Sigmund Freud (1900)
Foundation Series, Isaac Asimov (1951)
History of the Jews, Heinrich Graetz (1891)
Beginning to See the Light, Ellen Willis (1981)
Samson the Nazerite, Ze’ev Jabotinsky (1927)
The Puttermesser Papers, Cynthia Ozick (1997)
Daniel Deronda, George Eliot (1876)
The Boys of Summer, Roger Kahn (1972)
On Photography, Susan Sontag (1977)
Eichmann in Jerusalem, Hannah Arendt (1963)
Are You There God? It’s Me Margaret, Judy Blume (1970)
A Walker in the City, Alfred Kazin (1951)
Writing and Difference, Jacques Derrida (1967)
Later the Same Day, Grace Paley (1985)
The Old Country
Tevye, Sholem Aleichem (1914)
The Fixer, Bernard Malamud (1966)
The Dybbuk, S. Ansky (1914)
The Family Mashber, Der Nister (1939)
World of Our Fathers, Irving Howe (1976)
The Jewish Government, Lamed Shapiro (1919)
The Yeshiva, Chaim Grade (1968)
Folk-Style Stories, I.L. Peretz (1908)
Suffering & Loss
Ringelblum Archive (1944)
A Tale of Love and Darkness, Amos Oz (2002)
The Destruction of the European Jews, Raul Hilberg (1961)
Life and Fate, Vasily Grossman (1959)
Survival in Auschwitz, Primo Levi (1947)
The Jewish War, Flavius Josephus (75)
King of the Jews, Leslie Epstein (1979)
The Ghetto Fights, Marek Edelman (1945)
The Trial, Franz Kafka (1915)
Man’s Search for Meaning, Viktor Frankl (1946)
Night, Elie Wiesel (1960)
Dolly City, Orly Castel-Bloom (1992)
The Garden of the Finzi-Continis, Giorgio Bassani (1962)
Maus, Art Spiegelman (1991)
Prisoner Without a Name, Cell Without a Number, Jacobo Timerman (1981)
Darkness at Noon, Arthur Koestler (1940)
The Iron Tracks, Aharon Appelfeld (1998)
What is Judaism?
The Bible
Babylonian Talmud (770)
Birnbaum Siddur, Philip Birnbaum (1977)
Tsene-Rene (1590s)
Kaddish, Leon Wieseltier (1998)
Commentary, Rashi (11th c.)
Sefer Hasidim, Rabbi Judah of Regensburg (early 13th c.)
From There Shall You Seek, Rabbi Joseph Dov Soloveitchik (1978)
Sipurei Masiyos, Rebbe Nachman of Breslov (1816)
Guide for the Perplexed, Maimonides (12th c.)
Shulchan Aruch, Yosef Karo (1565)
Man Is Not Alone, Abraham Joshua Heschel (1951)