Start with high-confidence humor essays books, then narrow by subgenre or adjacent topics.
If You Lived Here You'd Be Home by Now
Christopher Ingraham
You Can't Joke About That
Kat Timpf
The Noble Hustle
Colson Whitehead
Made in America
Bill Bryson
The Know-it-all
A. J. Jacobs
Stupid Things I Won't Do When I Get Old
Steven Petrow
Thurber on Crime
James Thurber, Robert Lopresti
Housebroken
Laurie Notaro
South Toward Home
Julia Reed, Jon Meecham
One in a Millennial
Kate Kennedy
Raw Dog
Jamie Loftus
Talk Southern to Me
Julia Fowler
Stay Hungry
Sebastian Maniscalco
Scrappy Little Nobody
Anna Kendrick
Big Dumb Eyes
Nate Bargatze
Idle Thoughts of an Idle Fellow
Jerome K. Jerome, Mint Editions
The Age of Magical Overthinking
Amanda Montell
Mailman
Stephen Starring Grant, Simon & Schuster Audio
One Man's Meat
Malcolm Hillgartner, E. B. White
