What Writers Can Learn from Letterman’s Top 10 Lists

The more I write, and analyze writing, the more important escalation seems. While an elemental aspect of narrative, escalation also appears significant in poetry, even (perhaps especially) in experimental work that (on its surface) appears to have no clear structure. Often, these works are structured, in that they escalate.

Let’s look at one of my favourite gags, the September 22, 1989 Top 10 list from Late Night with David Letterman. This show, which pre-dated Late Show with David Letterman, was well-known for its oddity. One night, Letterman rotated the camera 360 degrees over the course of the hour, so that for part of the show everything was upside-down. There was even an episode in which Letterman was too tired to really do a show.

The Top 10 list of September 22, 1989 was “Top 10 Numbers Between One and Ten”:

  1. Seven
  2. Four
  3. Ten
  4. Three
  5. Eight and a half
  6. Nine
  7. Two
  8. One
  9. Eight
  10. Five & Six (tie)

Let’s examine the writing choices here, and see how the joke operates through escalation, by setting up and then smashing expectations. You have to keep in mind that Letterman would be reading these out loud, one at a time, so that the audience would receive them very slowly compared to how quickly you just read down that list.

As soon as Letterman says “Number 10: Seven,” the audience knows that the numbers will be listed out of order. It seems like the regular escalation, from 1 to 10, is being thrown away in favour of randomness. On one level, this is true. There’s no reason that we begin with 7 rather than 3. On closer inspection, however, Letterman’s writers have made two careful choices that re-introduce some structure, and allow for escalation.

With “Number 6: Eight and a half,” Letterman throws a wrench into the entire joke. This operates almost like a plot twist might. The audience thought this was a silly, simple disordering of the numbers, according to no apparent logic. Now, however, we can see that Letterman is not just disordering the numbers, but playing around within the set. We are not just dealing with whole numbers. Now it is clear that he could throw in another fraction, or a decimal, or something along those lines.

Note that he does not. Why not? Why can’t Letterman say something like “Number 2: Five and Four-Tenths”?

Because there wouldn’t be any escalation. It would be the same joke, repeated. Once Letterman introduces “Eight and a half,” he makes it clear that the joke is not that the numbers from 1 to 10 are being ranked out of their “natural” order. This is the joke premise, but it is not the joke. The “jokes” happen when Letterman departs from ranking whole numbers randomly, and introduces some apparent order.

Note what he says instead for “Number 2.” First, note the position. This is the penultimate ranking. It’s the obvious place for another twist. We expect some crazy number, since we previously were given “Eight and a half.” What do we get? “Eight.”

Both “Eight” and “Eight and a half” are on the list.

What does this matter? It matters because it means — and if we are paying attention, we understand that it means — that not all of the numbers made the list. “Eight” is sort-of taking up two positions. So, one of the numbers must be left out. But which number?

Notice how this simple listing of numbers has managed to achieve something like a narrative drive. It begins in apparent randomness, with a catalytic moment of sorts: when the numbers begin ranking out of their natural order (the state of the world has been disturbed, like it typically is at the beginning of a story). Then there is something like a “plot twist” when Letterman reads “Eight and a half” — you might consider something like a conflict to be arising here, where we begin to wonder if he’s really going to read out all the numbers after all.

Then, we reach something like a crisis moment — he reads out “Eight” and we now have to deal with the suspense of whether or not the list will be completed. How could it be completed? This is the formulaic structure of a Hollywood movie. Here is the point in the film where it seems like the hero’s goal can never be accomplished. Letterman only has one slot left, for two numbers.

The solution is obvious in retrospect, but elegant in execution: a tie between Five and Six. Notice how this move resolves the apparent conflict that began arising with “Eight and a half” and seemed unresolvable with “Eight.” You almost breathe a sigh of relief as you laugh out loud.

The Structure Below the Surface

Hiding this sort of narrative structure beneath text that appears, on its surface, to lack structure, is one of the most useful writing techniques I have come across. This is how David Lynch works. He puts together events that appear to make very little sense. However, they always feel like they make sense, because he slavishly follows narrative structure. Scenes begin, escalate, and end. They may do so in absurd ways, and not seem to accord to any sort of narrative logic, but they always feel like they are proceeding logically.

Or listen to the song “Jizz in My Pants” by The Lonely Island — notice how the song escalates. It takes less and less, smaller and simpler things, to make him jizz in his pants. Eventually, he jizzes before he even has a chance to tell you what caused him to do so.

What unites narrative and poetic logic is this very sense of escalation, of producing and developing conflicts — however small, silly, or strange.

The First One's Free.

The First One's Free.

To celebrate (over) a decade since my first book, I’m offering it for free.

EX MACHINA is a choose-your-own-adventure-style poetry-novel hybrid about how machines have changed what it means to be human.

Fill out this form so we can stay in touch, and I’ll send you the book.