From Gotham Humor Writing Instructor Bruce Cherry:
Write your own David Letterman-style Top Ten list (Or Top 5. Whatever number works best for you.)
The key is using some of the templates that the Letterman show pioneered. They really illustrate the point that the jokes seem to write themselves. For example:
“Ten Things Overheard at ____.” Just fill in the blank with anything from notorious items in the news like “This Year’s Oscars,” maybe something a bit more creative like, “Vladimir Putin's Birthday Party.”
“Rejected ______.” This can be wildly varied. Think of things like “Rejected Avengers: Endgame Characters” or “Rejected Children’s Toys.”
“Signs that You've Got a Bad ______.” Again, anything from “Signs You've Got a Bad Dentist,” or “Streaming Service,” or “Yoga Instructor.”
So Much Happiness
Read Naomi Shihab Nye’s poem “So Much Happiness,” and then think of a moment when you were so filled with happiness that you floated, and
“Even the fact that you once lived in a peaceful tree house
and now live over a quarry of noise and dust
cannot make you unhappy.”
If you need a little inspiration, read the replies to this thread by New Yorker writer Rachel Syme, who asked people to describe “a very specific memory of a day you remember being truly, totally happy, the more details the better,” and then she matched the moment with its perfect perfume.
Now, describe someone all floaty with joy performing an ordinary task — biking to work, frying an egg — and show that they’re happy, without telling it.
Best Vacation Ever
Imagine characters taking a trip — this can be a family, a group of friends, a married couple — that they’ve meticulously planned for a long time. Write about their trip, and make all of their carefully laid plans go wildly, unpredictably, (maybe hilariously) wrong. BUT the trip should still ultimately be the best one they’ve ever taken.
Go Back For Seconds
Make a list of all of your favorite foods, the best meals you’ve ever eaten, and dishes you’ve devoured and loved and never been able to find again. Make this a very, very long list.
Choose the one that makes your mouth water the most, and write a scene of a character slowly eating and savoring it. (Remember, work outside your genre. So if you’re a memoirist, make it fiction! If you’re a novelist or screenwriter, go ahead and re-create the experience of the meal, if you want.)
You May Already Be a Winner
Write a scene of someone achieving a long-sought goal, or winning a prize, or accomplishing something they once thought impossible. If you need inspiration, watch as many videos as it takes of Olympic gold medalists, the final round of the Scripps National Spelling Bee, or The 25th Annual Putnam County Spelling Bee, or people winning a new car on the Price Is Right.
Worst Advice Ever
Make a list of all the times people gave you really bad advice. Try not to go too dark here, and to capture the good intentions of folks who were just trying to help. Now, create a fictional advice columnist and have them respond to letters with the more flagrant examples of terrible advice. Make it clear that this columnist is big hearted, but needs to find another line of work.
Take a picture, it’ll last longer
Go outside, if you can, someplace where you can observe people, like a park or a public plaza. Take a picture of someone engaged in a moment of joy. It can be people — a kid on a playground swinging as high as they can, friends hugging hello, someone enjoying a perfect latte or cupcake — but it doesn’t have to be. A little dog proudly carrying a big stick, a squirrel finding a strawberry, birds singing their flock home at twilight — these moments will also do.
Make the subject of your photo a character and write a story about how they reached this happy moment. Look at the photo often and imagine the character's joy for as long as it takes.
