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If you loved

Books like Calypso

A darkly hilarious and unexpectedly tender meditation on the absurdities of aging and the inescapable gravity of family. These 12 books are the closest matches in mood, pace and themes, with what each one shares with Calypso.

  • bittersweet
  • melancholic
  • intimate
  • sun-drenched
  1. 01

    Best of Me

    David Sedaris

    A masterclass in observational comedy that invites you to laugh at the absurdity of human nature before quietly breaking your heart.

    Shares:
    • bittersweet
    • wry
    • self-deprecating
    • aging and mortality
  2. 02

    Let's Explore Diabetes with Owls

    David Sedaris

    A globe-trotting masterclass in finding the hilarious, grotesque, and surprisingly tender details hidden in everyday life.

    Shares:
    • wry
    • self-deprecating
    • aging and mortality
  3. 03

    I might regret this

    Abbi Jacobson

    A funny, vulnerable road trip through the messy realities of relationships and self-discovery.

    Shares:
    • intimate
    • wry
  4. 04

    Trick Mirror

    Jia Tolentino

    A razor-sharp, dizzying plunge into the funhouse mirror of modern internet culture and millennial self-delusion.

    Shares:
    • wry
  5. 05

    Vacationland

    John Hodgman

    A hilarious, painfully self-aware stroll through the haunted forest of middle age and the unforgiving beaches of New England.

    Shares:
    • melancholic
    • wry
    • self-deprecating
  6. 06

    Wow, No Thank You.

    Samantha Irby

    A laugh-out-loud, unapologetic ode to the exhaustion of getting older, leaving the house, and having a human body.

    Shares:
    • intimate
    • wry
    • self-deprecating
  7. 07

    Broken

    Jenny Lawson

    A wildly funny, deeply vulnerable plunge into the chaotic reality of living with severe mental illness.

    Shares:
    • darkly comedic
  8. 08

    Furiously Happy

    Jenny Lawson

    A wildly tangential, laugh-out-loud manifesto on fighting crippling depression with weaponized absurdity.

    Shares:
    • darkly comedic
  9. 09

    I Remember Nothing and Other Reflections

    Nora Ephron

    A sharp, hilarious, and ultimately heartbreaking conversation with your smartest friend over a very good lunch.

    Shares:
    • bittersweet
    • intimate
    • wry
    • self-deprecating
  10. 10

    Consider the lobster, and other essays

    David Foster Wallace · 2005

    A dizzying, hyper-articulate plunge into the absurdities and moral anxieties of modern American life.

    Shares:
    • wry
  11. 11

    Take the cannoli

    Sarah Vowell

    A deadpan, deeply nerdy road trip through the weird, haunted, and hilarious corners of American culture.

    Shares:
    • wry
    • self-deprecating
  12. 12

    Don't Get Too Comfortable

    David Rakoff

    A bitingly funny, Wildean grand tour through the absurdities of American overconsumption and the special circle of gilded-age hell we've built for ourselves.

    Feels:
    • hilariously horrified
    • absurd
    • cynical

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