Ten Ways to Turn a Simple Observation into Stand-up: With Iliza Schlesinger

Chris Head
6 days ago
6 min read

Iliza Schlesinger had the experience of asking a man on a date what his middle name was. He told her, but he didn’t follow up by asking hers. This didn’t feel right. How does the bare bones of this become stand-up – and how can you create stand-up out of your own simple observation?

In this excerpt from one of my Zoom stand-up comedy writing classes, I break down the techniques Iliza Schlesinger uses. Chances are lots of this was happening instinctively. But by consciously identifying the techniques you can use them yourself more readily. Remember that comedy writing is about both playful spontaneity and conscious reworking and analysis. You need to switch between the two modes.

1. Rule-of-Three

This is a classic that I describe this as the "Monday, Tuesday, Banana" technique.

The Structure: Establish, Reinforce, Surprise.
The Logic: Two items are the minimum needed to create a pattern; the third item is the curveball that breaks it.

Note that "Monday, Banana" doesn't work because there is no pattern to break, and "Monday, Tuesday, Wednesday, Thursday, Friday, Saturday Banana" is excessive! Sometimes being verbose is funny, but all things being equal comedy works best when it’s economical and tight.

Iliza Schlesinger example: She does two ‘threes to open the bit. This is a quick way of getting a couple of laughs as she sets-up her tale.
Try it: Set up a list of three, where one and two suggest what the third one is going to be… and then subvert that expectation. The bigger the surprise the bigger the laugh.

2. Misdirection

Rule-of-three contains misdirection. It’s the classic set-up/payoff device.

The Hook: You lead the audience down a garden path by making them expect something –
Payoff: - but then you go somewhere else.
In a ‘three’: In the rule-of-three the first two parts are the misdirection and the third is the payoff.
Try it: Aside from the three, always look to surprise your audience and misdirection is a great tool to achieve that.

3. What If?

This is the engine of premise-based comedy.

The Process: You take a real-life situation and ask, "What if...?" to find a comic angle.
Example: "What if you went into an antiques shop in year 3000?" or "What if a surgeon acted like a mechanic?" You can simply imagine a situation playing out differently – changing the How it happened. Or you can make a bigger change, altering the Who, Where or When.
Iliza Schlesinger examples: There’s a quick one earlier on: “What if he was asked why he didn’t ask my middle name?” Subsequently, “what if I could break up in my most perfect fantasy way?” (Changing How it happened) Also, “what if the magical ability to start an argument were literally a magic show?” (Changing Who & Where)
Try it: This is at the heart of comedy – what if things were different? Try taking a situation and change the how, the who, the where or the when.

4. What If? Inside/Outside
A classic device is to contrast what you’re doing or saying in a situation with what you’re actually thinking.
Outside: You might, for example be saying something polite and appropriate...
Inside: You’re thinking rude and aggressive thoughts.
Iliza Schlesinger example: On the date she is raging inside that he hadn’t asked her middle name, but on the outside, she is smiling and nodding.
Try it: Create a dramatic contrast between what you’re saying or doing and what you’re thinking. (Often the outside is moderate while the inside is extreme).
Note: She says she “planned the break-up… on the first date”, which highlights the inherent absurdity and sets up a question we want answering: “what was the plan?” Setting up a question (often at the start) is always great for audience engagement.

5. Is Likes (Comic Analogies)

I refer to these analogy jokes as "Is Likes" because they often literally link two ideas with the phrase "It's like..."

The Goal: To express a specific opinion through a vivid, surprising connection.
The Leap: The key is to be clear on the point you are making first, then find a distant, surprising comparison that illustrates it perfectly.
Iliza Schlesinger example: The female ability to create an argument out of nothing is like magic. Which leads to the above ‘what if?’ – what if it were literally a magic show. Which is itself a great example of an act-out (see below).
Try it: Get into the habit of exploring analogies, “is likes”. Many you come up with won’t feel that funny, but the good ones can become strong laughs in the set.

6. Act Outs

An act-out is when a solo comedian performs a dialogue between two or more characters, often using different voices, physicality and mime (or “object work”).

Showing then Telling: In stand-up it’s often a case of telling the joke, or describing the comic situation, then showing it. So, after you deliver a verbal joke, you "act it out" to escalate the comedy.
Iliza Schlesinger example: She does act-outs all the way through. She seldom just tells, she also shows. A striking example is the aforementioned magic act act-out.
Try it: If you’re not doing act-outs, you’re missing a massive trick. Start small with sprinkling in direct quotes in other people’s voices (you don’t have to be a great impressionist to do this). Build up to acting out dialogue and situations.

7. Undercutting

This is where something serious, dramatic, or high-status is abruptly undercut by something trivial or banal.

Build up and knock down: It involves some kind of big build up, which is misdirection because… it’s going to be undercut.
Iliza Schlesinger example: She builds up the question: how could you possibly make yourself cry….? And the answer is plucking out a nose hair.
Try it: Always look to be building things up and then knocking them down.
Note: As I note elsewhere, framing an absurd idea as advice for the audience can add to the comedy and she does that here.

8. Small to Big

It’s very common to start somewhere big then undercut it with something small, as above. But you can also go the other way round.

The small: You start with somewhere "small" and then abruptly jump to something “massive."
Iliza Schlesinger example: In her example of how women can create arguments out of nothing, she goes from an annoying “cough” to “World War III”.
Try it: If you’re going to say something really big, preface it with something really small to create a sudden leap.
Note: When she says she wants “to take the argument outside so the neighbours can see”, as she says to her boyfriend, “how you treat me”, she immediately says to the audience, “it’s fine, he treats me fine”. This suggests to me that in a previous telling the audience worried for her at this point, which would get in the way of the laugh. Sometimes the audience needs reassurance to laugh.

9. Tangents

A tangent is way of embedding a short routine or observation into a longer one.

Feeling of Spontaneity: They make the performance feel spontaneous. A tangent suggests you can't help but follow a side-thought which has the feeling of being unplanned.
Iliza Schlesinger example: She goes off on a tangent about The Bachelor.
Try it: Look for a short bit or joke that would work as a tangent off a longer piece and try folding it into the bit you’re working on. It’s often the case that it can get bigger laughs as an apparent spontaneous aside than it did as a stand-alone piece.

10. Callback

A callback is when you refer back to a joke or concept from earlier in the set, but in a new context.

The Reward: It rewards the audience for listening and creates a "you had to be there" intimacy.
Iliza Schlesinger example: The whole set has been building up to the middle name callback.
Try it: In the Schlesinger routine the beginning and ending are tied in together, and it feels like she knew the ending and then worked out how to build up to it. However, where this isn’t the case, if you are stuck for an ending, try looking for something from earlier that you can bring back in a new context.

My next stand-up comedy writing classes on Zoom begin on Monday 12th January. Info and booking