Here’s my second note for Comedy Writing for Late Night TV (here’s the first note). Some meta points: I tried reading this with the tips I linked to about How to Read a Book (PDF).

  • I did a one hour reading session.

    • 6 minutes previewing: I always estimate that I can read 1 minute per page so I marked off the next 44 pages. I also thought of some questions to keep in mind after skimming.

    • 19 minutes reading: For a pomodoro

    • 5 minute break: Ok so this break makes it 65 minutes total

    • 25 minutes reading:

    • 10 minutes writing: That’s when I did the vomit draft of this post.

  • I ended up reading 83 pages in 44 minutes of reading and I felt very focused. I’m not sure if it’s meditation or what. I think it’s meditation. I noticed a lot faster if I wasn’t paying attention to the book so I didn’t need to re-read. I also was reading a hard copy of the book. I’ll see how helpful it is when I try this on a Kindle book.

Okay, enough writing about reading.

As mentioned, I had some questions in mind while reading. I’ll answer those now, for this post.

How can I apply what I learn?

I don’t work for a late-night TV show. I don’t write comedy regularly. I’m not part of a writing team. What I have in common is that late-night TV is the schedule. I’m trying to write every day. Their writers write every day. I’m trying to write entertaining posts. Their writers are focused on entertainment.

This reminds me of Ben Orenstein (developer at thoughtbot) mentioning that a tech talk should be entertaining. It’s not always the underlying point of a talk, but entertainment is the most effective use of the medium. If you want to get your actual point across, be entertaining. Here are some of Ben’s tips and a great talk about this: How to talk to developers (Rails Conf 2013).

The challenge in applying this is that I might not have an actual point.

What are the main points of the chapters I’ll be reading?

The chapters I read were about sketches. Beyond the monologue, writers create jokes for the other segments. Here are the different types of sketches in each chapter:

  • Joke basket sketches: These are collections of jokes built around a theme but without a storyline. Joe Toplyn explains how to create characters for these sketches. I mentioned my first post on this book that I used to catch a lot of The Tonight Show. My dad would watch a VHS recording of it every morning when I was growing up. I really enjoyed seeing Jay Leno’s Mr. Brain as a character example.

  • Story sketches: A story sketch is your traditional comedy sketch. He explains the steps then breaks down a story sketch called “SFX Burglar” on Conan O’Brien, showing how each step is applied. It was really cool to read his step-by-step explanation, read the raw script, and then finally watch the sketch on YouTube.

  • Parody sketches: Similar to a story sketch but based on existing things. He does another explanation and breakdown. This time it’s the “Oil of OJ” sketch on Jay Leno. I thought everything was on the internet but I couldn’t find this clip. The explanations are detailed. Joe Toplyn even shows example lists of associations that lead to the combinations used in the “Oil of OJ” sketch.

I’m really really enjoying this book. And I liked the results of this hourly reading breakdown. I have about 140 pages left. I might be able to finish the book in a couple hours and have a couple drafts of book note posts to share.


I’m trying the following breakdown that fits into three 25-minute time blocks (5-minute breaks in between):

  • First block: Six minutes of pre-reading. I mark an estimate of what I’ll read in the session. This time I marked off 80 pages. That was aggressive—I ended up reading 63 pages. I skimmed the chapters and wrote the names down. Then I wrote a couple questions down (How can I apply these techniques to writing and blogging?). Then I read for the remaining 19 minutes.

  • Second block: Read for the entire 25 minutes.

  • Third block: The old vomit draft. Trying to get from beginning to end. First an outline then filling in what I can. I’ll get better at this.

The chapters I’d be reading were about semi-scripted pieces and semi-scripted field pieces.

Live semi-scripted pieces

An example of a semi-scripted piece is a stunt piece, like David Letterman’s velcro suit. I mentioned in the first book note post on this that Joe Toplyn writes particularly straightforward for a book about humor. He saves that for the sidebars. I enjoyed the story he shared about developing the suit of Alka Seltzer:

A staff member tested the suit in rehearsal and, sure enough, as soon as the Alka-Seltzer started bubbling he began to suffocate.

The book also shares another principle, “Don’t literally kill anybody.” (The staff member lived.)

Semi-scripted field pieces

Everyone had their different file sharing means in college. “Back in my day…” Ok yeah actually back in my day we used DC++. One of the things that got around pretty quickly freshman year1 was this folder of Conan O’Brien clips. One of them was Triumph, the Insult Comic at the premiere of The Phantom Menace.

So I was happy to see it as an example in the book. Joe Toplyn deconstructs punchlines from the segment and explains associated pairs that could have led to it.

Triumph tells one of the only young females he found among the crowd of males, “You can choose from all kinds of guys who have no idea how to please you.”

A female fan + Star Wars fan association (“sexually inexperienced”) = “All these guys have no idea how to please you.”

Reading this, it made me realize that while some jokes may very well be ad-libbed on the spot, many were likely written ahead of filming. It’s cool to see how a segment like this could be planned.

Directives from the book

Here are my key takeaways from the book:

  • Write a lot: Writing teams probably write ten times as many jokes as appear on the screen.

  • Pick an angle: Take something real and recognizable then add an angle to it.

  • Use association lists: Association lists are the basis of getting to all of those jokes.

Cranking out jokes day in and day out doesn’t happen without some kind of structure. I found this really encouraging:

This process may seem formulaic […]

Professional writers juggle the formulas in their heads—automatically, instinctively—but that doesn’t mean the formulas don’t exist.

Now I just need to practice for twenty years.

  1. Association list: things that get around quickly + freshman year of college

He is Late-Night

I liked the format of writing separate notes for Grit. I’m giving that another shot. I write better book notes posts when I write as I read. When putting longer book notes posts together, sometimes I worry that excerpts are all coming from the same chapter. If I write while reading, I can cover sections while they’re fresh in my head. Diving back into a book’s highlights weeks or even months after reading the book means overcoming a good amount of inertia.

Comedy Writing for Late Night TV1 is by Joe Toplyn. He knows Late Night TV. In The Last Samurai, Tom Cruise asks if one of the leader’s knows the samurai well and he’s told that “he is samurai”. Late Night with David Letterman, The Tonight Show, Late Show with David Letterman. Emmys. Everything. Joe is late night TV.

Joe distills that knowledge into straightforward breakdowns of writing techniques. It makes it clear that writing jokes can be mechanical. And if there’s a system, it can be taught and learned.

The only jokes are the jokes themselves, all pulled from jokes that aired on TV shows. He doesn’t punch up the explanations with humor. It’s straightforward. He lays out the underlying concepts, explaining how each concept is applied to all sorts of segments you see on comedy shows. The same concepts are used on the monologue, headlines, desk pieces, sketches, prop pieces, and on and on.

When I was a kid, my dad taped2 The Tonight Show. While I got ready for school, my dad would be drinking coffee and watching Jay Leno3. There’s an interesting morning ritual. Years later, my dad lost The Tonight Show and the Sonics in a very short, very rough span.

I’ll continue writing a couple notes posts as I read through the book. And sometime down the road I’ll try writing a few jokes. It’s gonna be very rough.

  1. It’s not available on Kindle so it’s the second physical book I’ve bought this year (the first is Ego is the Enemy).

  2. If you don’t know what “taping a show” is, then you probably weren’t alive when my dad was taping The Tonight Show.

  3. I’m part of a generation that seems to hate Jay Leno because of the whole Conan O’Brien feud. Whatever, I like him.