Writing/humor
Where’s Your Sense of Humor?
An award-winning author shares how to find humor in everything you write
Every year after winning the Pulitzer Prize for humor, I’m besieged with questions from new writers about how I went about writing my award-winning humor pieces. They run the gamut from “What in the world were you thinking?” to “Were you drunk when you wrote that?”
So, to clear up the confusion, I thought I’d take a moment to offer a few suggestions on how to write stunning humor pieces, unlike anything people have seen before.
What most non-writers don’t know is writing brilliant humor pieces is infinitely harder than writing non-fiction. The best humor pieces are steeped in research. For instance, my article, The Greatest Stories Never Told was preceded by several minutes of intense Googling before I put pen to paper; or in this particular case, fingers to keyboard.
I’ve identified six successful formulas for writing award-winning humor. They include:
· Combine two items that conflict with each other
· Expose true stories
· Push the discussion to the limit
· Wonder to yourself, “What if?”
· Have fun with history
· Fantasize with your fantasies
Combine two items that conflict with each other
One of the easiest ways to come up with award-winning humor pieces is to combine two disparate items and figure out a way to combine them together into a story.
Years ago, when steroids first became big news in the Tour de France, I thought to myself, I wonder if they have problems with steroids in international chess tournaments? What would happen if a 13-year-old kid got busted for using them? The result was Steroids Invade the World of Chess.
Another time, I was watching an old episode of “Leave It To Beaver,” the stories of an average kid growing up in the 1960s in an average family. But, then I thought, The Beaver never gets into serious trouble; like snorting coke or selling meth from his bedroom. What would it be like if Wally, Lumpy, and the whole Cleaver clan got involved in running a million-dollar methamphetamine ring in Mayfield? So I wrote Breaking Beav (a take-off of the popular series, Breaking Bad).
Expose true stories
I’ve led an interesting life. Most of us have. So, if we stop long enough to remember the good old days, we can usually come up with tall tales to share with our reading audience. One of my early pieces, I Competed Against a Serial Killer on the Dating Game was based on fact. In 1972, I was an out-of-work ski instructor with plenty of time on my hands, so I auditioned for the popular daytime show, “The Dating Game.” I didn’t have to embellish the story; I actually did compete against a convicted serial killer that somehow slipped through the cracks.
I ended up writing an entertaining story about how Maurice Micklewhite (Michael Caine), Issur Danielovitch Demsky (Kirk Douglas), and Chaim Klein Witz (Gene Simmons) got their names.
Fast forward to 2008, I was a single, lonely and horny guy living in Vail, Colorado with plenty of time on my hands. I thought to myself, Dang! I need to get myself a woman! The popular dating site, Match.com was all the rage, so I crafted an honest, heart-felt profile and waited for my phone to ring. It never did. So, I thought, What’s the one thing that all women say they want? Why, a great sense of humor, of course! So I went to work writing the profile in Expelled from Match.com! a fictional, off-the-wall dating profile guaranteed to reel in the prospects. Within a matter of hours, my email box was inundated with messages from lascivious women wanting to know who in the heck wrote that hilarious profile. I have to meet him.
Another of my favorite pieces is Five Minutes from Lorraine, the true story about how I was almost named Lorraine by my parents. I had so much fun researching baby names — like Bronx Mowgli, Moxie CrimeFighter, and Nakoa-Wolf Manakauapo Namakaeha Momoa — that I ended up writing an entertaining story about how Maurice Micklewhite (Michael Caine), Issur Danielovitch Demsky (Kirk Douglas), and Chaim Klein Witz (Gene Simmons) got their names. The rest is history
Push the discussion to the limit
Another guaranteed way to write entertaining humor pieces is to take a simple topic and blow it completely out of proportion. For instance, when I heard that the 2020 Olympics (postponed to 2021) banned all spectators from viewing the competitions in person, I thought What’s next? Banning the Olympic venues? So, I wrote about the popular Zoom app in Zooming Toward the Olympic Games. The concept was “we don’t need Olympic venues anymore.” Instead, all 11,000 athletes can compete from the comfort of their own homes.
That story was preceded by my piece, We’ve Become Too Politically Correct! following the news that the popular California ski resort, Squaw Valley finally knuckled under pressure to change their name to, Indigenous North American Native Woman of the Lowlands.
Wonder to yourself, “What if?”
At the core of all good humor writers is a healthy imagination. Good humor writers need to be able to shun “what is,” and replace it with “what if?”
Long before the 2021 Olympics, I read an article about all of the off-the-wall “athletic” events that have been rejected from Olympic competition; events like holding your breath underwater, decimating pigeons with shotguns, hot-air ballooning, and shin-kicking. So, I wrote Olympic Sports that Never Quite Made the Grade, an entertaining story of what’s involved in making the grade as an Olympic event.
After several years of enduring the infamous “Nathan’s Hot Dog Eating Contest,” every Fourth of July, it became obvious to me that we needed a change. So, I came up with a list of substitutions for hot dogs in future events that included three new categories: Insects & Reptiles, Animal Sweetbreads, and Non-organic Hardware. Sweeping Rule Changes for Eating Competitions is the unfortunate result.
I wondered what it might be like to live with two left feet, eyes in the back of my head, and to be all ears, as well as being green with envy, tickled pink, and white as a sheet.
Another time, I was riding the bus to work, when I read an advertisement that touted the value of assigning federally-incarcerated inmates service dogs to help calm them down. But then I thought, Well, that’s all well and good for the inmates, but what about the poor dogs who are suddenly jailed through no fault of their own? So I wrote Paws for Prisoners to describe to readers what it’s like to be jailed from a dog’s point of view. The results aren’t pretty.
Finally, way back in 2006, I was a semi-finalist in the June-July 2006 Humor Writing Contest by America’s Funniest Humor Showcase for my article, Birth Anomalies I’d Like To Have. Since then, I’ve revamped it to My Favorite Birth Anomalies. In the article, I wondered what it might be like to live with two left feet, eyes in the back of my head, and to be all ears, as well as being green with envy, tickled pink, and white as a sheet.
Have fun with history
For all of you history buffs, there are plenty of great ideas for humor by sifting through the past. One night I was watching an old TV western where paw said that maw was dying of consumption. I thought, what in the heck is consumption? so I rolled up my sleeves and found dozens of old-time diseases that nobody seems to suffer from anymore: bilious fever, chin cough, crop sickness, dry bellyache, grocer’s Itch, not to mention bucket fever. In Those Good Old Time Diseases, I wondered why we never hear of those? Of course, I can’t remember the last time I was asked on a health history questionnaire, “Are you now, or have you ever suffered from canine madness, the cooties, dropsy, dog bark, dancing mania, Winterbottom’s sign, softening of the brain, or Egyptian inheritance?”
In my article Customs, Laws and Faux Pas, I was surprised to learn that:
· It is a misdemeanor in California to shoot any game from a moving vehicle unless the target is a whale.
· Citizens of Devon, Connecticut are prohibited from walking backward after sunset.
· It is against the law for Florida residents to dream about another man’s wife or cow, and for men to be seen publicly in any kind of strapless gown.
So, I went ahead and wrote a lengthy description of things to be aware of as you travel around the country this summer.
Finally, The Golden Era of Cigarette Ads brought back memories of the lengths that Madison Avenue went to in order to hook randy young servicemen returning from World War II on tobacco products for life. In humor, the truth is often the most painful.
Another great source of material lies right in front of your eyes: headlines in the news. In my second book, Watching Grandma Circle the Drain, I wrote a section called, Ripped from the Headlines. One of the first articles was For Better or for Worse, the story about a guy who was fed up with dating, so he decided to marry himself. It’s followed later by The End of a Love Affair, the sad story of how he discovers that he’s been fooling around on himself and filed for divorce.
Fantasize with your fantasies
If you completely run out of ideas for something to write about, you can make something up! That’s the beauty of being a writer — you can pull things out of thin air and write about anything you want. In my third book, Monkey in a Pink Canoe, I wrote a piece surprisingly titled Monkey in a Pink Canoe about what happens when a guy gets cornered into explaining the birds and the bees to his six-year-old nephew because his parents didn’t have the courage to do it themselves. Confused about how to approach the subject, he attempts to tone things down by using “socially acceptable” terms along with street slang like bald-headed yogurt slinger, one-eyed trouser snake, and choke the chicken to get the message across.
Readers will thrill to the stories of Charlton Heston’s homosexual threesome with Yul Brynner and Vincent Price.
Another subject readers love is show business; especially all the lurid details behind making your favorite movies. So, I wrote The Greatest Stories Never Told to describe what really went on behind the scenes of Hollywood blockbusters like The Ten Commandments, Ben Hur, The Sound of Music, and Titanic. Readers will thrill to the stories of Charlton Heston’s homosexual threesome with Yul Brynner and Vincent Price. How when filming The Sound of Music, because of the severe drought, the location scout had to rent 5,000 acres of AstroTurf from the Pittsburgh Steelers for Julie Andrews’ signature song. And why a miniaturized Titanic was built for a cast of 450 “small people.”
Finally, after years of dating, I describe how I fell in love with Alexa, my artificial intelligence application in I Had a Passionate Love Affair with Alexa. What started out as a casual affair, turned out to be a scorching, one-sided romance until I swapped her out for Siri.
So, the question is not where do I find humor to write about? In reality it should ask where isn’t there something humorous to write about? It’s all around us. A good humor writer excels at opening themselves up to life and looking for the irony in it.
