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Books like The Rum Diary

Hunter S. Thompson · 1998 · US · literary fiction
★ 3.85 Goodreads · 67,766 ratings

In 1958, Paul Kemp, a young freelance journalist, takes a job at a failing English-language newspaper in San Juan, Puerto Rico, and drinks, brawls and drifts towards trouble, in Thompson's early autobiographical novel.

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12 books for readers of The Rum Diary

The Dud Avocado

Elaine Dundy · 1958 · US 96% match ★ 3.66 Goodreads · 11,220 ratings
shares: expatriate, 1950s, romantic · easy read, intimate

A 21-year-old American heiress loosed on Paris with pink-dyed hair and an evening dress before breakfast blunders through affairs, parties, and a budding self-knowledge.

Factotum

Charles Bukowski · 1975 · US 96% match ★ 3.91 Goodreads · 78,320 ratings
Book 2 of 5 in Henry Chinaski
shares: autofiction, alcoholism, dark humoured, addiction · easy read, intimate

A drunk drifts through menial jobs across 1940s America, refusing to hold any of them, in Bukowski's picaresque ode to the dignity of not trying.

The Sun Also Rises

Ernest Hemingway · 1926 · US 94% match ★ 3.78 Goodreads · 513,342 ratings
shares: expatriate, alcoholism, romantic · intimate, easy read

American expatriates drink, fight, and fall apart in 1920s Paris and Pamplona, trying to find meaning after the war took it all away.

Sex and Rage

Eve Babitz · 1979 · US 94% match ★ 3.54 Goodreads · 21,171 ratings
shares: autofiction, alcoholism, addiction · easy read, intimate

Jacaranda Leven, a surfer and party girl who drifts through Los Angeles at the end of the 1970s, starts writing seriously and moves to New York, and has to decide what she will give up to keep going.

Hot Water Music

Charles Bukowski · 1983 · US 94% match ★ 3.86 Goodreads · 16,619 ratings
shares: autofiction, alcoholism, dark humoured, addiction · easy read, intimate

Short stories of drunks, failed writers, gamblers and the women who put up with them, set in the bars, racetracks and cheap apartments of Bukowski's Los Angeles.

The Bell Jar

Sylvia Plath · 1963 · US 94% match ★ 3.94 Hardcover · 1,532 ratings
shares: 1950s, autofiction, dark humoured · intimate, easy read

A young woman's descent into depression in 1950s New York, told with razor wit and suffocating clarity.

Babylon Revisited and Other Stories

F. Scott Fitzgerald · 1960 · US 93% match ★ 3.98 Goodreads · 5,948 ratings
shares: expatriate, alcoholism, romantic · intimate, easy read

Fitzgerald stories from 'The Ice Palace' and 'Winter Dreams' to 'The Rich Boy', and the title story of a reformed drinker who returns to Paris after the crash to win back his young daughter.

Islands in the Stream

Ernest Hemingway · 1970 · US 93% match ★ 3.88 Goodreads · 17,618 ratings
shares: alcoholism, Caribbean · easy read, intimate

Thomas Hudson, a painter living alone on Bimini, is visited one summer by his three sons; later, in Cuba during the war, he hunts German submarines with his boat.

Big Sur

Jack Kerouac · 1962 · US 92% match ★ 3.83 Goodreads · 39,174 ratings
shares: autofiction, alcoholism, addiction · intimate, easy read

Worn out by the fame On the Road brought him, Kerouac's stand-in Jack Duluoz hides in a friend's cabin in Big Sur to dry out, and the solitude turns into something closer to a breakdown.

The Lonely Londoners

Sam Selvon · 1956 · Trinidad and Tobago 92% match ★ 3.70 Goodreads · 14,718 ratings
shares: 1950s, Caribbean · intimate, easy read

Moses Aloetta, an old hand in London, meets the new arrivals from the West Indies at Waterloo station and helps them find rooms and work through the grey seasons of the 1950s.

Under the Volcano

Malcolm Lowry · 1947 · UK 91% match ★ 3.76 Goodreads · 27,738 ratings
shares: expatriate, alcoholism, addiction · intimate, cold

A drunk ex-consul in a Mexican town on the Day of the Dead, 1938, stumbles through the last twelve hours of his marriage, his life, and a novel built on twelve Faustian chapters.

Giovanni's Room

James Baldwin · 1956 · US 91% match ★ 4.34 Goodreads · 309,459 ratings
shares: expatriate, romantic · intimate, easy read

An American in 1950s Paris confronts his homosexuality through a love affair with an Italian man, and the novel's claustrophobic intensity mirrors the impossibility of the closet.