5 Books That Always Make Us Laugh

I fell in love with Katherine Heiny’s writing after reading her entertaining short story collection Single, Carefree, Mellow in 2015, and her newly released first novel, Standard Deviation, has all of the same wit and charm. This debut focuses on Graham Cavanaugh and his second wife, Audra, whose outgoing, chatty nature in no way resembles his first wife Elspeth’s reserved, quiet one. Graham and Audra are raising a son with Asperger’s, struggling to define their marriage, and, in the midst of it all, form an off-kilter friendship with Elspeth while escorting their son to origami conventions. Heiny’s examination of marriage and parenthood is equal parts hilarious and tender. 

Chicago-based humor writer and blogger Samantha Irby chronicles her dumpster fire of a life in achingly honest and acerbically funny essays. She touches on the absurd: witnessing a Civil War reenactment while on her way to a wedding reception, a humiliating road trip in college, and adopting her cat, Helen Keller. But Irby also writes with incredible authenticity about the not-so-funny parts of her life: her struggle with depression, her alcoholic father and disabled mother, and her choking fear of death. Roxane Gay calls it “as close to perfect as an essay collection can get.” 

This memoir by the creator of 2 Broke Girls is filled with self-deprecating, knee-slapping humor. Whitney Cummings makes light of her misadventures—like having her severed ear sewn back on, or nearly ending up in a Guatemalan jail—but at its heart, this book examines Cummings’ mental health, her lack of self-esteem and why the best medicine for anything especially cringe-worthy is laughter.

From standup to Sooo Many White Guys to 2 Dope Queens (the podcast and the show), Phoebe Robinson can’t stop, won’t stop. Now the super funny polymath is getting laughs with her second bestseller, Everything’s Trash, But It’s Okay. In this wildly funny, deeply personal, and crucially timely collection of essays, Robinson explores gender, race, dating, the time she met Bono, and the OTHER time she met Bono.

These hysterical musings on aging from the writer behind Sleepless in Seattle and You’ve Got Mail are not to be missed. You’ll be nodding along as Ephron waxes poetic about female maintenance (relentless regiments of Botox and hair dye), the underrated reality of an empty nest, and the nirvana achieved when sinking into a good book. Ephron’s brutally honest voice and dry humor are what we miss most about her, but reading these makes us feel like we’re cozied up with a wise, older friend.