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Books like A Supposedly Fun Thing I'll Never Do Again

David Foster Wallace · 1997 · US · essays
★ 4.12 Goodreads · 57,079 ratings

Essays on state fairs, cruise ships, tennis, and television that reveal the absurdity and melancholy hiding in American entertainment culture.

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12 books for readers of A Supposedly Fun Thing I'll Never Do Again

Trick Mirror

Jia Tolentino · 2019 · US 96% match ★ 4.01 Goodreads · 80,179 ratings
shares: essays, cerebral, witty, cultural criticism · idea-driven, ironic

Nine essays on how late-2010s America scams itself, the internet as self, the wedding industry, athleisure and optimisation, written from inside the trap by someone who does not pretend to be above it.

White

Bret Easton Ellis · 2019 · US 95% match ★ 3.46 Goodreads · 6,133 ratings
shares: essays, cultural criticism · low-key, cold

Bret Easton Ellis's essays on post-Empire America: celebrity, social media and the fate of the transgressive artist in a culture that demands likability.

The Philosophy of Modern Song

Bob Dylan · 2022 · US 94% match ★ 3.80 Goodreads · 4,037 ratings
shares: essayistic, essays, witty · clear-cut, unhurried

Sixty-six short essays on songs by other people, from Stephen Foster to Elvis Costello, each with a riff on what the song is really about.

The White Album

Joan Didion · 1979 · US 94% match ★ 4.01 Goodreads · 54,414 ratings
shares: observational, essays · cold, ironic

Didion's essays on California from the late 1960s into the 1970s, from the Manson murders and the Doors in the studio to the Getty museum and the Black Panthers, set beside her own breaking nerves.

A Room of One's Own

Virginia Woolf · 1929 · UK 94% match ★ 4.22 Goodreads · 285,054 ratings
shares: essays, cerebral, witty · idea-driven, hopeful

Woolf's lecture-turned-book on why women who want to write need five hundred a year and a lockable door, in a voice that invented its own form of argument.

Slouching Towards Bethlehem

Joan Didion · 1968 · US 94% match ★ 4.18 Goodreads · 89,636 ratings
shares: observational, essays · ironic, idea-driven

Joan Didion reports from a late-1960s California coming unglued, from Haight-Ashbury to a murder in the San Bernardino Valley, in essays cut like tile.

The Writing Life

Annie Dillard · 1989 · US 94% match ★ 3.98 Goodreads · 18,922 ratings
shares: essayistic, essays · intimate, idea-driven

Dillard's short book on the daily work of writing, the cabins and studies where she has done it, and what it costs, with a detour to a stunt pilot who wrote in the sky.

The Empathy Exams

Leslie Jamison · 2014 · US 94% match ★ 3.67 Goodreads · 16,129 ratings
shares: essayistic, essays · idea-driven, unhurried

Essays that start from Jamison's work as a medical actor, paid to perform symptoms for students, and move through Morgellons, ultramarathons and her own body to ask what empathy is for.

Less Than One

Joseph Brodsky · 1986 · Russia 94% match ★ 4.34 Goodreads · 1,412 ratings
shares: essayistic, essays, cerebral · idea-driven, unhurried

Brodsky's essays on growing up in postwar Leningrad, on his parents, and on the poets he loved, Akhmatova, Mandelstam, Auden and Cavafy among them.

When You Are Engulfed in Flames

David Sedaris · 2008 · US 94% match ★ 4.08 Goodreads · 220,287 ratings
shares: essays, dark humoured, witty, comic · funny, ironic

Sedaris on quitting cigarettes by moving to Tokyo for three months, on domestic life with Hugh in Paris and Normandy, and on the neighbours, strangers and medical complaints that keep finding him.

On Photography

Susan Sontag · 1977 · US 94% match ★ 3.87 Goodreads · 60,646 ratings
shares: essays, cerebral · idea-driven, low-key

Six essays on what it means to see the world through photographs, and what the camera consumes, numbs and moralises away.

Notes of a Native Son

James Baldwin · 1955 · US 94% match ★ 4.36 Goodreads · 26,012 ratings
shares: essays · idea-driven, unhurried

Baldwin returns from Paris to America to bury his father, and in ten essays lays out what the country's racial lie has cost a son, a church, and a prose style.