How do I write a funny David Letterman style TOP TEN LIST? We’ll teach you!


Like many of us, I started watching David Letterman’s Late Night Show in the 80s. His laid back self-deprecating comedy made his show fresh and unique.  It also featured hilarious recurring characters  like Larry Bud Melman, Mujibur and Sirajul and Flunky the Clown.  Plus, creative segments like “will it float?” and stupid pet/people tricks.  And of course the best of all…THE TOP TEN LIST!!

This is how you write a funny David Letterman style TOP TEN LIST.

  • 10. Choose a funny topic.  Something you’d enjoy writing about. 
  • 9. Do your initial research to mine for ideas.
  • 8. Make a quick list of funny-sounding related words/phrases.
  • 7. Think of the dichotomy (opposites are funny).
  • 6. Use lots of descriptive adjectives.
  • 5. Don’t be afraid to get a cheap laugh.
  • 4. Use alliteration (several words that start with the same letter).
  • 3. Push the envelope. It’s OK to be edgy. Probably a good idea actually.
  • 2. Don’t be afraid to create absurd scenarios.  Comedy is weird. 
  • 1. GET STARTED!!

I’m going to teach you how to write your own funny top ten list and the tricks to craft your ideas into a tight cohesive package. So it’s humorous to even someone who isn’t familiar with the subject.  This guide will break it down into several steps.  I will include loads of joke examples and a bunch of my personal lists as a case study. I’m excited! Let’s do this.

The first list debuted in 1985 (Top Ten Things That Almost Rhyme With Peas).  These amazing collections were packaged in a way that allowed for sooo much comedy.  I read the first two top ten list books in the early 90s and I remember crying laughing.  I had never laughed like that while reading a BOOK!!  It was life-changing. 

After that day, all my funny ideas filtered through a sort of top ten generator in my brain. Training that muscle has been extremely beneficial as well.  I find it helpful in designing t-shirt logos or coming up with several slogans or ideas on short notice. 

Plus, if you’re ever feeling uninspired just go back and re-read some of Dave’s lists.  Of course, his classic delivery made them even more hilarious.  Maybe he won’t be reading your list to millions of viewers but you can still use this format to entertain. 

It works on social media or for wedding speeches or a retirement party or a work function.  There are plenty of opportunities for funny content to entertain.  A well written top ten can be the hit of the event.

Why a Top Ten List?

The reason I like the Top Ten format is that it doesn’t have to be complete jokes.  You don’t have to be long-winded with structured framing and resolution.  It only needs to be funny ideas, blurbs or word pairings. Basically all punchlines.  Just as long as they’re related to the subject.  Frankly, sometimes they aren’t and that makes it even funnier. 

In theory, it would seem more difficult to come up with ten punchlines instead of one solid crafted joke.  But the system that we use is similar to a professional comedy writer.  Start with a premise and then spitball every related topic within 6 degrees and condense it down to funny ideas, phrases, and statements. PLUS, even one or two really good punch-lines can make the list a home run. Got it?  OK, let’s look at the case study.

Case Study. Candice and Dayna go to Peru.

Before we proceed. The young girl under the table was attempting the peace sign but her other finger was blocked.  I took the opportunity and turned it into a thug life meme!! lol.

In 2014 my friends traveled to Peru to work in an orphanage and hike Machu Picchu. To me, this was an ideal premise for comedy.  Peru is funny for several reasons.  They’re kind of an uncivilized culture (or at least appear to be) and they’re a tourist trap.  The second you get off the plane they throw a baby alpaca in your arms and want you to pay for a picture.  All these things add up to good jokes.  I created 4 top ten lists regarding their trip.  Before, during and after as well as a Spanish language top ten.  We’ll breakdown the techniques I used to create each one. 

HOW TO GET STARTED.

Before their trip, I knew little about Peru.  So I pulled up the wiki page.  Everything from geographic location to clothing, cuisine, and culture.  It sounds time-consuming but you can mine a ton of comedy in a few minutes.  Ponchos, Alpacas, Pisco, Ayahuasca, Lake Titicaca, Machu Picchu.  All of which are funny words and sounds.  Just imagine Dave reading them aloud. 

My most common theme when creating a list (or any comedy frankly) is the dichotomy between the key subjects.  2 single party animal Canadian girls accustomed to western amenities, traveling to an isolated, ancient culture. It sounds like a corny sitcom but it’s RIFE with jokes.  It’s like Laverne and Shirley went to Peru.  Um, let me update that.  Imagine the Kardashians went to Peru.  Even just the thought of that sparks a comedy flame.  Can you feel it?

THE FIRST TOP TEN LIST.

TOP TEN things Candice and Dayna MUST do in Peru

10. Enter and win a wet poncho contest
9. Care for babies at orphanage including diaper changing, burping, and breastfeeding
8. Teach at least one Incan how to twerk
7. As an act of friendship, Candice will give away her hideous denim vest to local Peruvian wanker
6. Dayna must buy authentic Alpaca fur Snuggie
5. Take 14-hour bus ride to Lake Titicaca. Get out….giggle….14-hour bus ride back
4. Get loopy on coca leaves and flash the natives
3. Scale summit…..enjoy endless salad bar and breadsticks at Machu Picchu Olive Garden
2. Have a torrid affair with leather-faced llama herder named Pablo
1. Eat ceviche till you hurl!!

The standout for me is #3.  The insane notion of having an Olive Garden atop an ancient Incan monument is what makes me laugh.  Another ridiculous idea is taking a 14-hour bus trip to a lake just to get out and giggle.  Normally that wouldn’t be funny but fortunately, the place is named TITICACA. This word would be funny to even a 5 year old.  So exploit it.  Nothing wrong with a cheap laugh.  Also, note the overtly descriptive phrases.  A torrid affair with leather-faced llama herder.  Most of the time simple is better but occasionally wordy can be very funny.  

You’ll notice in most top tens, the number one joke is generally the shortest.  Often only two or three words.  The final entry gives closure to the list and resolution to the reader.  Hopefully, they’ve enjoyed it, they’ve gotten a laugh and they leave feeling satisfied.   

In my number one, I used the word “hurl” as opposed to “barf or puke” because it sounded better in the phrase, but I’d imagine spew could’ve been substituted with a similar effect. I approach my top tens as if Dave were presenting it. So make sure it’s Lettermanesque.

While writing your #1 envision Dave cheerfully, quickly announcing the conclusion to the list, Paul Schaefer cueing up the band and music playing while Dave prepares for the next segment.  Keep that visual in mind.  It may help you close out the list.

THE SECOND TOP TEN LIST

Here’s our second top ten.  Candice and Dayna are still in Peru. They were relieved that it’s quite civilized and actually had many western comforts, including McDonald’s.

TOP TEN differences between North American and Peruvian McDonald’s

10. Peruvian Big Macs have 2 juicy 100% alpaca patties
9. Deep fryers are operated by screeching spider monkeys
8. 95% of franchise earnings funneled to local drug cartel
7. Instead of Ronald McDonald, their mascot is Fernando the pipe-smoking drifter
6. Happy meals include the same toy for boys and girls. A typhoid inoculation
5. McFlurrie options……Oreo crumbs, Reese’s Pieces or Ceviche!
4. Oversized drink straws can also be used for jungle blow darts
3. Soda fountain offers Coke, Diet Coke or Ayahuasca
2. All employees wear freshly pressed poncho and name tag
1. Chicken McNuggets are actually made from real chicken!!

That was another example of a dichotomy. With jokes stemming from the contrast between familiar McDonald’s items and completely opposite food common in Peruvian culture.  Also anything fast food-related has a ton of potential laughs.  People naturally perceive fast food as processed, non-nutritions and calorie-laden. So it’s easy to poke fun of.

You’ll notice my use of adjectives like “juicy” alpaca patties or “screeching” spider monkeys.  I also like alliteration (two or more words starting with the same letter).  So it has a flow.  The phrase “freshly pressed poncho” is funnier than just poncho.

Another thing I like to do is push the boundaries.  Not to be offensive but I like to poke fun at the obvious.  My reference to drug cartels isn’t to upset anyone it just happens to be a fact of central American life.  Edgy?  Kinda.  Offensive?  I don’t think so. I’ll leave it up to you with how far you want to take it.  Comedy has a wide-ranging spectrum.  From Seinfeld to Saget or Carrot Top to Carlin.  All funny, all different degrees of irreverent.  **side note. See how I used alliteration to get my point across just there.  Notice the flow of how it reads and sounds in your head.  I use that trick a lot and it makes for a more enjoyable joke experience.   

THE THIRD TOP TEN LIST

In this next section, I thought it would be fun to come up with ten Spanish phrases Candice could use on her trip.  I didn’t do any language fact-checking BTW.  I just wrote the list in English and dumped it into Google translate.  Whatever popped out was fine.  Nobody’s going to challenge it. 

DIEZ frases en español útiles para Candice en Peru
TOP TEN useful Spanish phrases for Candice in Peru

10. Alguien robó mi chaleco denim. llame a la policía!!
Someone stole my denim vest. Call the police!!

9. Dónde está la más cercana Arby’s?
Where is the nearest Arby’s?

8. Creo que su alpaca está muerto Senor.
I think your alpaca may be dead.

7. Este bebé es feo. ¿Puedo cambiar por una atractiva uno por favor?
This baby is ugly. May I exchange it for a more attractive one?

6. Mi poncho huele a huevos podridos.
My poncho smells like rotten eggs.

5. Dónde está el Pepto Bismol? Estoy teniendo diarrea explosive.
Is there any Pepto Bismol? I’m having explosive diarrhea.

4. Llamas a esto CEVICHE!? Usted debería avergonzarse!!
You call this CEVICHE!? You should be ashamed!!

3. Este collar de maíz seco que parece ser de una calidad excelente.
This dried corn necklace appears to be of excellent quality.

2. Hay una escalera mecánica a la cima de Machu Picchu?
Is there an escalator to the top of Machu Picchu?

1. En Canadá, mi apodo es Screech. Pero me puede llamar El Screecho!!
*smoke-filled seedy bar*
*Candice slams double shot of pisco….slowly wipes her mouth tilts back in chair and says*
“In Canada, I’m known as Screech………in Peru call me…….El Screecho!”

Here’s why it’s funny.  If you’d traveled to a foreign country you’d learn the most common useful phrases.  You probably wouldn’t be asking for the nearest Arby’s.  You wouldn’t…I would. 

I also ignored the rule of short and sweet number ones.  Typically I would never write something so long but in this case, I was trying to entertain a scepcific group.  Mainly those that know Candice.  But even though you don’t know her the list is still humorous.  My favorite part of this list is the term El Screecho.  Its just fun to say.  Lol

THE FOURTH TOP TEN LIST

The final top ten was a follow up on what they’d learned during their trip. 

TOP TEN things Candice and Dayna learned in Peru

10. Everyone there talks in some funny language
9. Sharing a single bed with Dayna after a fish and bean dinner is a bad idea
8. Host family hates when you finish the Alpaca milk and put the empty carton back in the fridge.
7. Buying an uncut kilo of cocaine much easier than in Calgary
6. Topless sunbathing at beach is illegal but no one seems to enforce it
5. Wearing an extra poncho is a handy tip on chilly Peruvian nights
4. Foot tattooing much less painful after 40 Coronas
3. Enduring 3 weeks without sex is like level ten on Angry Birds……really effin hard
2. Loose rocks at Machu Picchu make yoga pose selfie difficult BUT not impossible
1. Mancora? More like Manwhore-a!!!

On the final list, I presented the girls as modern Millenials just out to party.  From a completely simple and ignorant perspective.  They’re good sports so I knew they wouldn’t mind me poking a little fun.

We tackled several funny scenarios.  Sharing a bed, staying with a host family, abstaining from sex, and surviving less than optimal weather and terrain.  When you’re attempting a list put your self in the shoes of others.  What perspective do they have and how can you wring comedy out of it.

And so that breaks down part one of writing your own Letterman style top ten list.  I have written dozens over the years.  Food and drink, sports-related, gym/workout, specific cities. my nephews. In our next blog, we’ll take on some more lists and break them down even further.  By the time we’re done, you’ll be able to craft a solid Top Ten on your own.  Even if you have a less than formidable funny bone.

If you’ve written your own list and would like to share it I’d love to read it. Send it to my DM @tshirttimemachine on Instagram!

matt

I'm the guy who creates the weird, funny t-shirts, as well as blog posts and tutorials. I'm going to share absolutely everything I know about my 20+ years selling online. Hopefully, it's helpful and entertaining. Welcome!

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