@ggf.nyc asked me this question in my thread about my humor website, but it made more sense to tag it on to everybody’s else’s answers. He wanted books specifically about New York, too. I did some hunting on my shelves and came up with a load of possibilities.
Terry Southern was the best dark humorist of the era. He’s known for Candy but try Flash and Filigree. The Firesign Theatre stole that novel’s “What’s My Disease” game show as “Beat the Reaper.” And by all means listen to the Firesign Theatre. My roommate and I would not only memorize their records, but try to uncover ever allusion and reference.
Bruce Jay Friedman. Robert Coover’s Pricksongs & Descants is one of the great collections of short stories. Don DeLilloGreat Jones Street is about early rock in Greenwich Village. He’s a 70s writer but close enough.) Philip Roth for Goodbye, Columbus and Portnoy’s Complaint, his early Newark novels. E. L. Doctorow for books about New York, with Ragtime and Billy Bathgate the lightest. The Book of Daniel isn’t funny but packs a punch.
Donald Barthelme’s short stories could be hilarious. So could some of John Barth’s. The Sot-Weed Factor is very long and not my taste but some says it’s his best.
Jean Kerr’s books of humorous essays were the bestselling ones in the fifties, topped by Please Don’t Eat the Daisies, later made into a film and sitcom. She wrote about life in the New York suburbs. Cornelia Otis Skinner was another major writer of humorous essays. And of course Erma Bombeck was already writing her column and collecting those in books.
Work through the names in The Playboy Book of Humor and Satire. Most of those already mentioned in this thread are there, but others aren’t like Shepherd Mead (good novels, too), William Iverson, H. Allen Smith (lots of 40s writing about New York). Playboy did another half dozen paperbacks collecting their humor, but they’re relatively easy to find. Dan Greenberg is in several and had a number of books as well.
When Jack Paar hosted the Tonight Show, he brought on wits and raconteurs who loved to talk. Many of them wrote funny memoirs that sold like crazy based on those publicity or maybe because of their great titles. Alexander King - Is There Life After Birth? Jack Douglas - My Brother Was an Only Child. Oscar Levant - Memoirs of an Amnesiac. Patrick Dennis. Brits Robert Morley and Peter Ustinov’s books were bigger in England, but everything is findable somewhere. Jonathan Winters broke out on Paar’s show. Few remember he wrote several books, including Mouse Breath, Conformity and Other Social Ills. Cliff Arquette played hayseed Charley Weaver and got several books out of it.
Bruce Jay Friedman also edited an important anthology titled Black Humor. It shades over into nonfiction, but a must if you want to take a deep dive into that era.