The 5 Funniest Books Ever

We asked comedy greats to name the five works in their fields that influenced them the most and made them laugh the hardest. Few authors are better suited to thrive in our fast-paced and distractible moment than Samantha Irby, who blogs, hosts live shows, and writes in print (including the bestselling essay collection We Are Never Meeting in Real Life) and for television (the upcoming comedy Shrill, which arrives on Hulu March 15). Across every medium, Irby combines an unflinching honesty about her own physical and psychological struggles with an unfettered joy.

Also read Tig Notaro’s favorite stand-up specials, Tracy Oliver’s favorite funny movies and Michael Schur’s favorite funny TV shows.

Me Talk Pretty One Day, David Sedaris (2000)

I remember being on the bus, going to work, reading the essay where he talks about going to speech therapy for his lisp. And I was laughing out loud, which was a humiliating thing to do. When I read this essay collection, I didn’t know that you could view what you’ve gone through a comedic lens and then work it out on the page. The story about his brother, the rooster: I remember being slack-jawed. I didn’t know people could work through their trauma in this way. Throughout my writing career, I have always looked to him as someone who does what I aspire to do. He is probably the pinnacle of this: taking a dumb thing that happened to you and telling it to someone else in a way that is relatable and funny.

Skinny Dip, Carl Hiaasen (2004)

The closest category I could put this novel in is like a caper: It’s just chasing through Florida swamps with people trying to murder each other. There are alligators and fishermen and all these insane characters. It’s really hilarious. And I love the idea of vengeful women: it’s how I try to live my life.

Hyperbole and a Half, Allie Brosh (2009)

My friend sent me this cartoon called “This is why I’ll never be an adult.” It was like this person was speaking my experience directly to me. She writes a lot about being depressed and anxious, accompanied by these super crude and hilarious cartoons. And it really is hysterically funny while also being painful in that way where you’re like, “Oh, I recognize myself in this.”

The Misadventures of Awkward Black Girl, Issa Rae (2015)

I’m proud to say that I’m an Issa Rae hipster. I was with her from the beginning, waiting for her to upload new episodes of her web show. When she put out the book, it was so relatable; I saw so much of myself in her that it was almost shocking. Her voice, her phrasing — it’s just like listening to someone you know tell all of these stories about her life: about being in chat rooms, eating alone or the extreme awkwardness you feel in social situations.

Made For Love, Alissa Nutting (2017)

There’s a con artist who loves dolphins a little too much, a tech billionaire trying to kidnap his wife to put a microchip in her brain and so many other hilarious bizarro characters. It’s a sharp and incisive skewering of tech culture and greed disguised as a zany screwball novel, and it’s basically perfect.

As told to Andrew R. Chow.