Inspiration Engagement Pieces 2020-09-03 00:00

How to Learn Storytelling from Stand-Up Comedians

learn storytelling from standup

In a classic episode of The Fresh Prince of Bel-Air, Will’s friend Keith, played by D.L. Hughley, is in town to do some stand-up comedy gigs.

Will decides that being a stand-up comedian is just about being funny on stage and telling a few jokes, so he signs up for a comedy showcase to prove it to his friend. Then he bombs miserably and uncomfortably from the moment he takes the microphone.

He tells jokes that normally kill with his family and friends, making fun of his cousin Carlton’s height, but the audience doesn’t laugh. Eventually, his buddy jumps on stage to save the set, and Will admits to him that his job is difficult.

  1. Stand-up comedy is more than jokes – it’s storytelling
  2. Every comedian has a distinct voice
  3. Bill Cosby: Don’t rush your story, as long as you can keep them interested
  4. Jerry Seinfeld: Want to tell good stories? Put in the work
  5. Steve Martin: Be fearless
  6. The most fun you’ll have learning about writing

Stand-up comedy is more than jokes – it’s storytelling

I’m a huge fan of stand-up comedy – but mainly, classic stand-up comedy.

To me, the prime years of stand-up were the ’80s and ’90s. Comedy was breaking ground, it was popular, and it was a launch pad for a lot of big-time careers.

Comedy specials littered cable TV. The comedian standing in front of a faux brick wall was a staple – joking about childhood, the differences between men and women, and the political scenes of the time.

One of the reasons, I feel, that I was pulled into stand-up comedy so much was because I enjoy a good story. Comedians that stand the test of time are actually expert storytellers.

They don’t just tell jokes with punchlines, like Will did. They craft narratives that take you on a ride of some kind.

In my opinion, there aren’t that many good ones left. John Mulaney is a noted exception, as he often creates long, winding stories with excellent payoffs, like the best meal he ever had in his life.

Watch that five-minute routine and notice all the little details about the diner, the song, the guy who is there with his kids… it all creates this tiny little world. Even the little twist halfway through is so perfect that the audience applauds.

That’s storytelling. And that’s what we want to learn today.

I’d like to tell you that I’ve studied comedians for decades now, but I’ve just watched and listened to a lot of stand-up comedy because it makes me laugh.

But as a writer, there are certain valuable lessons I’ve pulled out over the years that I think would be valuable to you.

Disclaimer: These are comedians I enjoy. This is not an exhaustive list of the greatest comedians ever. Some didn’t fit this article, others I’m just not as familiar with. But these are good ones, that’s for sure.

Every comedian has a distinct voice

The first thing everyone urges you to do is have a voice as a writer.

Your voice dictates the tone in which you present your material. Authors with distinct voices stand out among the pack. If you don’t develop your voice, you’ll be forgettable.

This is also true in comedy.

Think of some of the most memorable comedians in history and how clear their voices are:

  • Bill Cosby: Mild-mannered storyteller, father figure (more on him in a second)
  • Robin Williams: Manic, zany, unpredictable
  • Garry Shandling: Self-deprecating, sad clown
  • Steven Wright: Non sequitur, bizarre
  • Jerry Seinfeld: Observer of everyday life
  • Steve Martin: Oddball, goofy
  • George Carlin: Acerbic, angry

The list goes on, but you get the idea. A stand-up comedian has a clear voice. You should, too.

How do you develop that voice? That one’s easy: just keep writing.

All writers start out emulating the people they admire. Over time, they massage and adapt that impression into something that mirrors their own point of view and eventually becomes an original tone.

Go dig up early George Carlin and Richard Pryor routines from the ’60s. They wore suits, had clean haircuts, and told jokes just like any other comedian of the time. They became successful once they developed their own voices and looks – and that came through work.


Bill Cosby: Don’t rush your story, as long as you can keep them interested

All right, let’s get this out of the way: as a human being, Bill Cosby has been revealed to be horrid. I don’t need to say any more than that. His talent as a stand-up comedian in no way excuses his behavior.

That said, if you can separate his career from his personal life, his career is a model for what storytelling can do for you. By creating entire worlds around his humor, Cosby was not just a pioneering comedian, but also a pop culture phenomenon with Fat Albert & The Cosby Kids and completely changed television with The Cosby Show.

For ages, Bill Cosby was the master storyteller. His bit on chocolate cake is proof.

The chocolate cake bit was legendary in my family growing up. Nearly any time we ate chocolate cake, someone would swing their fork around and sing, “Dad is great! Give us the chocolate cake!”

Here’s a link to the entire bit, and notice something curious: from start to finish, it’s nine-and-a-half minutes long.

That is an eternity for one bit. The average stand-up comedian is happy if he has ten or twenty minutes to use in an entire set. Cosby had almost ten on one bit alone!

When you watch and listen to the story, note how he pulls you in and paints the picture, and he takes his time with every detail:

  • His wife’s demand for him to make breakfast for the children
  • His desire to stay in bed
  • His wife’s threats of violence to get him to do it
  • His grumpy mood as he goes downstairs and starts making breakfast
  • His adorable daughter walking into the kitchen
  • Her request for chocolate cake for breakfast
  • His disbelief in the ridiculous request
  • His brain processing the request and justifying the idea

He hits “chocolate cake, coming up!” at exactly five minutes into that video. He still has to get to the other kids coming down, their joy at eating chocolate cake for breakfast, his wife coming downstairs and seeing it, getting mad at him, and punishing him.

This entire routine could be summed up as, “My wife made me make breakfast for the kids. I didn’t want to. The kids wanted chocolate cake, so I gave it to them, and my wife was mad at me.”

That is ultimately the entire point of the story. And it has zero impact when you tell it that way.

But the way Cosby unfolds this tale over the course of nearly ten minutes is masterful. Every detail sets it up, and the audience is along for the whole ride, laughing along the way.

And by the time he hits the end line of the entire bit, he’s got them because he pays off the beginning of the story: “And my wife sent me to my room… which is where I wanted to go in the first place!”

I’ll admit that I rush stories all the time. I skip over details and move the plot along so that the story has energy to it. We all can benefit from slowing down a bit and setting the stage. Not only does it paint a picture for the audience and rope them in emotionally, it gives you the opportunity to put in details that pay off the story later.

And it’ll become a story worth remembering.

Need a little help with pacing?

So, as we've seen, pacing is important in good storytelling. Your novel is probably longer than the material that will fill a ten minute comedy bit. ProWritingAid's pacing report gives you an overview of the pacing of your whole manuscript. It identifies the slower paced parts of your manuscript, such as introspection and backstory so you can spread them out.

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Back to those comedians.

Jerry Seinfeld: Want to tell good stories? Put in the work

Have you ever seen Comedian? It’s one of those documentaries that I think is never talked about on the level it deserves.

Let me set the stage for you: Jerry Seinfeld starred in the number one television show in America for years. Seinfeld is a stone-cold classic of a sitcom, just as hilarious today as it was in the ’90s. It made Jerry dump trucks full of money, power, and influence.

They ended the show after the ninth season, walking away from even more money, just so that they didn’t overstay their welcome.

And what did Jerry Seinfeld do? He went back to comedy clubs.

You see, in the ’80s and ’90s, television producers kept looking for the next big breakout stars, so they would hit the comedy clubs. They would pick out some great comedians and develop sitcoms around their bits.

That’s how big stars like Jerry Seinfeld, Roseanne Barr, Ellen Degeneres, and others all got their starts. It became part of the culture of comedians: the comedian that was using stand-up for bigger and better things.

Jerry could have retired quietly or gone on to do movies or other TV shows. Instead, he grabbed a notepad and started developing new material.

(He also retired all of his old material with his brilliant special, I’m Telling You For the Last Time.)

In Comedian, the camera follows Jerry around as he jumps into comedy clubs, doing surprise sets, and working out new material.

The documentary also shows plenty of instances where jokes didn’t work, Jerry bombed, and you can feel the goodwill of his decade-long success evaporate with an audience that didn’t care for the new jokes.


What you see throughout Comedian is Jerry tweaking stories, trying them out, and writing a lot of bad material.

And therein lies the genius.

How many of us writers sit down to write The Great American Novel out of the gate? We all think we can do it because others do it. Other writers can generate beautiful prose out of thin air!

But what we don’t see or realize, often, is that other successful writers have written a lot of garbage just like us. Jerry Seinfeld created a show that still influences comedy today. He has told jokes that are remembered thirty years later (What is the deal with corn nuts, anyway? Is it corn, or is it a nut?).

The reason Jerry and other comedians can say they can craft stories on stage that pull people in is that they have put in the reps. They have hustled. They have written garbage and performed it on stage over and over again, paying attention to how the audience responds and adjusting their writing to be better the next time around.

And even then, they still fail. If you want to succeed, don’t be afraid to fail.

If you get frustrated with your writing, watch this 2-minute clip of Jerry Seinfeld at the height of his fame completely losing his train of thought on stage at a comedy club.

Steve Martin: Be fearless

In Born Standing Up, his excellent autobiography, comedian Steve Martin gave out advice that has been quoted so many times it’s become a cliche: “Be so good they can’t ignore you.”

(It’s a fantastic book. It might be the only book I’ve sat down and read in one sitting, start to finish. I was up until 3am reading it, and I have zero regrets.)

However, there’s another great tip that you can absorb as a writer when you watch Steve Martin perform stand-up: throw your fears out the window.

As a self-published author, I’m involved with other authors who say you “can’t” do this or that. You have to “write to market,” which means studying what an audience wants and delivering it to them exactly.

Problem is, I hate that model.

It’s what causes me trouble as a fiction ghostwriter. Clients expect X, Y, and Z. I might deliver X, Y, and V – slightly different. They don’t like that. The job is to deliver exactly what readers expect. No risk-taking allowed.

You can build a great career on satisfying expectations. But Steve Martin built a legendary career on being completely and utterly different from anything else out there at the time.

In the 1970s, you had everyday humor from observational comics, incendiary humor from political comics, and the old-fashioned humor of the Catskills performers.

Steve Martin played banjo and made balloon “animals” that looked nothing like what they were supposed to be. And did it with a completely straight face.

When on The Tonight Show with Johnny Carson – the unrivaled Mecca for stand-up comedians looking for their big breaks – Martin performed a stand-up routine for dogs, complete with several live dogs sitting in front of him to play to (so he doesn’t have to add “canned barks” in later, he says). It gets funnier the longer it goes.

Talk about taking risks!

If you want to be memorable, you have to be willing to tell stories in a different and unique way. You have to spin things your own way (remember that voice you developed?) and commit yourself to it.

No, there’s no guarantee you will be successful. But you’ll have a greater shot at having a career or sphere of influence that is meaningful to you.

Case in point: Steve Martin was packing stadiums with tens of thousands of people to watch him do standup comedy. Then, one day, he just… stopped. It wasn’t fulfilling for him anymore.

He has always taken steps based on his own creative fulfillment, and that included having a little bit of courage. It’s not a bad way to go.

The most fun you’ll have learning about writing

Every day, take a few minutes to peruse YouTube and watch or listen to brilliant stand-up comedy of the past.

Pay attention to how these influential voices tell stories in their own unique ways. Notice the structure of their stories, the details, the little ways in which they add color (and I don’t just mean blue language), and how they can retain the honesty of their voices as they go from story to story.

Stand-up comedians learn how to tell great stories by going on stage and telling stories to crowds of people, live, every single night of the week. It is trial by fire, and when the good ones break through, you can pull a lot of value from their experiences.

You’ll learn to be a better writer if you pay attention to them. Plus, you’ll laugh a lot every day. And that’s good for everybody.

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