I Am Writing My First Ever 5-Minute Stand Up Comedy Set

Here is how I’m doing it

I made this image with ChatGPT, DALL-E, and Bing — Credit

Doing an open mic night at a comedy club has been on my bucket list for years. I love comedy and, while I’ve participated in some comedy-adjacent experiences, I’ve never done straight stand up at a comedy club.

When you write about comedy, you feel pressure to be hilarious on every line (I’ll throw in some jokes, but no promises that you’ll laugh out loud, slap your knee, or tickle your cricket).

Here is how I’m approaching writing my first 5-minute comedy routine.

What the Hell Are Comedy-Adjacent Experiences?

If that’s not the first thing you asked yourself when reading my intro, then you and I are not the same.

Comedy-adjacent experiences sounds like something a celebrity or politician would say to the judge when they’re trying to get out of a crime they just committed:

“Yes, I do admit that I was involved in some…law-adjacent experiences, your Honor.”

You’re going to a freedom-adjacent jail, motherfucker.

What I mean by “comedy-adjacent experiences” is that I participated in a talent show at a summer camp where I performed (and I use that term very loosely here) a mockery of a stand up routine based on an episode of Seinfeld.

There’s no time to explain exactly what I did but just imagine someone trying to do an exaggerated parody of a comedian.

For example, I walked on “stage” in suspenders and immediately said, “Is everyone ready to laugh?”

For whatever reason, the routine was a smashing hit. I tapped into some sort of comedic energy in the universe and the entire “audience” of fellow campers were in stiches. Yelling and screaming (merrily) ensued.

I should mention that I had no idea what I was doing.

When I was asked to “perform” two other times, I was extremely less funny. That was the end of my “performances” — if you can even call them that at all.

One other story.

I worked for a non-profit for 13 years where I taught personal development and relationship skills. Part of the training involved role-play scenarios. And in one of these scenarios, I had to portray someone being silly or funny.

Most of the time, I stuck to silly as it’s easy to be ridiculous.

But one time I decided to write a short, very adult, comedy script that I thought would work for a particular group.

In the skit, I referred to Hugh Hefner and insinuated that the other person in my skit had so much sex that they named sex positions after him: “You’ve heard of 69… but you’ve never heard of the ‘Buster 360’— it takes 3 or four people to make that happen.”

Just like at summer camp years before, the group leapt to their feet in uncontrollable laughter. Honestly, the feeling it gave me was phenomenal. Like I was some kind of comedy god (I’m not).

In one way or another, I’ve been chasing that “comedy high” ever since.

How I’m Writing My 5-Minute Comedy Routine

Now let’s get down to the nitty-gritty of what I’m doing.

First, I should say that I’ve studied comedy for years — I am obsessed with all things words, language, and communication.

I’ve watched and analyzed endless hours of stand up specials. I’ve read books on humor, biographies of famous comedians (like Steve Martin and Tiffany Haddish), not to mention so many articles on how to write jokes, stage presence, how to respond to hecklers, etc.

I find it all fascinating.

None of this makes me any funnier. That’s a fact. I don’t consider myself a funny person. Like most people, I have my moments among friends and family.

But jokes and comedy sets are extremely difficult for me to write.

Although I’d be lying if I said I didn’t enjoy the process.

Here’s how I’m approaching my comedy set:

• Find premises (ideas, topics, stories, etc.) that I think are funny (or have potential to be funny)
• List out all the ideas, thoughts, questions, contradictions, opinions, and (very importantly) assumptions I have about the premise
• Brainstorm what comparisons I could make related to the topic (old/young, believer/nonbeliever, etc.)
• Think about if I have any personal stories or anecdotes related to the topic or theme
• Ad lib and talk out loud until I come up with funny words, phrases, or bits
• Think about the assumptions and expectations for the premise. How could I subvert the expectations? What are the opposites? What is the most silly, outrageous, or most unexpected opposite?
• Start playing around with joke structures (set ups/punches, incongruity, comparison/contrast, impersonations, etc.). To me, this is about flipping ideas around in my mind, inspecting them from every possible angle, and seeing what strikes me as funny.
• Free write a bunch of jokes related to the premise (and everything that I’ve already done above).
• Start picking out jokes that I like and getting rid of others that are not as funny (to me).
• Put the jokes in some sort of order. Ideally, I prefer to start with my second-funniest joke and end with my funniest joke.
• Mix and match and arrange the jokes. This is all very loose and very changeable.
• Consider how to make the existing jokes better. Can I use funnier words? A funnier example? Body language? A voice? A prop?
• Try to make the set ups shorter and more concise while still being clear to the audience. Generally, an audience can’t laugh if they don’t understand the joke (unless, of course, THAT is the joke).
• All the while, I keep my mind and gut open to new jokes or new sides of the premise (new POVs) that I haven’t yet explored.

When I have a solid draft of a 5-minute set (like I do now), I begin to practice performing the routine out loud. I time myself. I figure out what words or phrases trip me up or are hard to remember.

I time myself with the clock on my cell phone.

Now that I’ve been doing all of this for about a week or so, I am starting to voice record myself. When I play the recording back, I listen for the flow and smoothness of my set, my pauses, my timing.

The next step is to video record myself.

When I do that, I’ll look for my facial expressions, body movement, presence, how I hold the “mic,” etc.

My Big 10 Tips for Writing Your First Stand Up Set

Since I’m not an expert, I thought I’d pretend to be one and still give you some advice.

I hope it helps.

Here are my big 10 tips for writing stand-up:

1. Write what you think is funny.
2. Say all of your jokes out loud and listen to how they sound.
3. Try to get a laugh (even a little one) immediately.
4. Figure out what you’re going to do with the mic and mic stand (don’t figure this out on stage in front of an audience).
5. Come up with smooth transitions between each part of your set.
6. Practice your routine 100 times before you go up on stage (you’ll be more confident).
7. Don’t overly rely on shocking, vulgar, or offensive material. Do the work to make the mundane interesting and funny.
8. Have at least one story (that you think is funny) that you can tell if you start to bomb on stage and need to abandon your material.
9. Know what you’re going to say to hecklers. I like the classic: “Hey, asshole, this is a one-person show…kind of like your sex life.”
10. Make your set funny to you. Enjoy the hell out of it. That way, even if you suck on stage, you will still have a good time.

Final Thoughts

Your job is to tell the truth — and make it funny.

And, even if you can’t do that, at least you’ve had a comedy-adjacent experience to tell your grandchildren. Probably around a digital campfire while wearing clunky VR headsets on post-apocalyptic Mars.

And for my parting act, I might just bring back the suspenders and attempt a 360-degree joke revival — it’ll require audience participation, but don’t worry, it’s all part of the show. 😉

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