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Leave the Short Pants Alone

The key to telling a funny story and getting laughs is when you tell the story and tell it like you’re trying to talk a cop out of your third speeding ticket in a month.
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July 16, 2025

A friend of mine, in his 60s, found himself back on the dating scene. He called and asked how to be funny. “Schiffy, I’m not funny. How do you do it? My last date was all crickets.” I laughed and said, “You were just funny. Crickets are funny. Do you know why you were funny? Because you didn’t try to get me to laugh.” 

Trying to be funny is the nail in the coffin. Observing a guillotining is less painful than watching a comic who’s lost the crowd attempting to win them back. 

Two critical ingredients for funny are likability and trust. If you don’t have either, it’s much more complicated. Now, let’s settle the class clown question. No, it is not a prerequisite for you to have been the class clown to be a successful comedian. 

Men will do things for laughs most women would never dream of. For instance, I’ve never seen or heard of women sneaking up behind someone and pulling their pants down. The last time I did it was 35 years ago. Anthony, who’s not my friend anymore, was wearing loose-fitting beltless short pants and talking to a table full of women in a vegan restaurant. His groin area was precisely level with the top of the table. I squatted down behind him and yanked. What I didn’t know was that Anthony didn’t wear underwear. The women at the table gasped.  I tried apologizing, but he never spoke to me again. Most failed jokes I don’t regret; this one I do.

My wife and I are strong community people, so we get invited to many weddings, bar or bat mitzvahs. A big yuck is when I’d fill a shirt sleeve with a dozen or so pieces of silverware and drop them on the floor in front of our hosts like I did at Paul Reiser’s son’s bar mitzvah. 

My favorite is to write a check for a few million dollars and send it back with the invitation. It’s something Jerry Lewis used to do. Since they all know that I am a comedian, it was always taken in the spirit it was intended, except once when, just like the short pants, this also backfired. 

I was performing on cruise ships when I met a newly married young couple. They were a magic act, but they hated the ships and wanted off. They told me their dream was to save enough money to open a small family restaurant in Mississippi. On the last day of the cruise, we exchanged phone numbers and addresses. A few days later, I wrote a two-million-dollar check and sent it to them as a joke. What I didn’t know was they were born-again Christians. His dad was the first on the phone when they called to thank me for sending them the two million.

His dad said in tears, barely speaking, “Jesus has used you to perform this miracle. God bless you, Mark.” Then he handed the phone to his son.  Again, “God bless you, Mark. We have more good news: Anne is pregnant; we’ve decided to name the baby after you.” With a deep breath and heavy heart, I said, “John, the check is no good. It was a joke. I didn’t know you’d take it seriously.” It got as quiet as if I had just delivered a death sentence. 

“What made you think sending us a phony check would be funny? What’s so funny?” In the background, I heard pregnant Anne, carrying my namesake, softly murmuring, “We’re not opening the restaurant?” They are good people. I hope they forgave me. 

The Jews are a great example of getting laughs through storytelling. But it’s not exclusive to just Jews. The key to telling a funny story and getting laughs is when you tell the story and tell it like you’re trying to talk a cop out of your third speeding ticket in a month. If you enjoy telling the story, tell it with enthusiasm; they will enjoy listening to it, and more than likely, they will laugh. The key is just to be yourself. And trust me, leave the short pants where they are and don’t send bad checks to born-again Christians.


Mark Schiff is a comedian, actor and writer, and hosts, along with Danny Lobell, the “We Think It’s Funny” podcast. His new book is “Why Not? Lessons on Comedy, Courage and Chutzpah.”

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