Books like

Books like Portnoy’s Complaint

12 books with a reading profile close to Portnoy’s Complaint by Philip Roth. Deep, inward-looking and thought-provoking; a moderate read.

1

The Beautiful and Damned

by F. Scott Fitzgerald

Also inward-looking and thought-provoking · literary, classic literature

Set in the shifting social landscape of 1910s New York, the narrative follows Anthony Patch, the presumptive heir to a massive tycoon fortune, and his marriage to the socialite Gloria Gilbert.
2

Schoolgirl

by Osamu Dazai

Also inward-looking and thought-provoking · literary, classic literature

The novella that first propelled Dazai into the literary elite of post-war Japan, Schoolgirl was essentially the start of his career and gained notoriety for its ironic and inventive use of language.
3

Washington Square

by Henry James

Also deep and inward-looking · literary, classic literature

In the affluent backdrop of mid-nineteenth-century New York, Catherine Sloper lives under the scrutiny of her father, Austin, a prominent physician who views his daughter as dull and unremarkable.
4

Tartuffe

by Molière

Also deep and thought-provoking · literary, classic literature

In seventeenth-century Paris, a wealthy patriarch named Orgon falls under the spell of Tartuffe, a man posing as a pious ascetic.
5

The Moon and Sixpence

by W. Somerset Maugham

Also deep and thought-provoking · literary, classic literature

Charles Strickland is an ordinary London stockbroker with a wife and two children until he abandons them without explanation and moves to Paris to paint.
6

An Occurrence at Owl Creek Bridge

by Ambrose Bierce

Also inward-looking and thought-provoking · literary, classic literature

Farquhar, a Southern planter, is being hanged for attempting to sabotage an Owl Creek bridge during the Civil War.
7

The Story of an Hour

by Kate Chopin

Also inward-looking and thought-provoking · literary, classic literature

Set in 1894, the narrative follows Louise Mallard as she receives news of her husband Brently’s death in a railroad disaster.
8

A Handful of Dust

by Evelyn Waugh

Also deep and thought-provoking · literary, classic literature

Tony Last is a gentle English country gentleman who lives at Hetton Abbey, a Gothic mansion he loves, with his wife Brenda and young son John Andrew.
9

The Portable Oscar Wilde

by Richard Aldington, Oscar Wilde

literary, classic literature

This 1946 compilation preserves the breadth of Oscar Wilde’s literary output, moving beyond his reputation as a mere wit.
10

A Rose for Emily and Other Stories

by William Faulkner

Also deep and thought-provoking · literary, classic literature

Faulkner's collection centers on the title story, in which the townspeople of Jefferson, Mississippi, attend the funeral of Miss Emily Grierson, a reclusive woman from an old family.
11

As You Like It

by William Shakespeare

literary, classic literature

In this pastoral comedy, Rosalind flees the court of her usurping uncle, Duke Frederick, and disguises herself as a young man named Ganymede to survive in the Forest of Arden.
12

Keep the Aspidistra Flying

by George Orwell

Also thought-provoking · literary, classic literature

Gordon Comstock, a young London poet, has quit a good advertising job because he despises the worship of money.

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