Inside Jokes: Josh Gondelman on 'The Entire Spectrum of Human Potential'

Inside Jokes: Josh Gondelman on 'The Entire Spectrum of Human Potential'
Stand-up comedian, Twitter champion, former preschool teacher, and Last Week Tonight with John Oliver scribe/producer Josh Gondelman is gearing up for the release of his second comedy album, Physical Whisper, out now via Rooftop Comedy.
The stand-up record is full of brilliantly funny and evocative stories. We asked Gondelman to deconstruct one such bit called "The Entire Spectrum of Human Potential," which documents a profound mass transit trek through New York with his then-girlfriend, as they encounter a mystical former professor who's now a homeless alcoholic and a young boy who is as wide-eyed and curious as can be.
First, listen to the joke here:

While Gondelman describes it as a "fairly entry-level premise" in terms of NYC stories, he tells it with compelling twists and turns. The story is real but we wanted to know how it got into his act in this form.
How soon after this situation did you recognize its potential for a funny story?
That happened right away. The joke accordioned outwards. I had that experience where I jumped too quickly from "Oh, what an interesting, fascinating person whose life has taken a very difficult turn," to "Oh, this guy's a lying son of a gun." That was the original kernel of the bit.
But it ends up being six, eight minutes and that's because, as I told it, there was more to the story and more to make fun of, of myself, and of the situation. I didn't want to de-humanize this person because that wasn't the joke. The joke was that I was blown away by this circumstance and immediately pivoted to mistrust and cynicism. So I needed to establish the wonderment I felt at first, because otherwise it's just, "Hey, a person down on his luck said something and it wasn't true. Isn't this guy a dick?" And that's not the story.
So, it ballooned outwards from beginning and end and I needed to create distance to add more jokes and observations. It happened very quickly, but it was too cynical when I started thinking about it and telling it on stage. So, it got progressively nicer and [more] genuine and introspective.
There's a perception that a comedian or observational storyteller has a mind that never turns off. Have you experienced situations where you didn't recognize material until way after the fact?
Definitely. There's a bit on my first album about a classroom full of four-year-old girls who wanted to marry this one specific boy in the class and he said, "I'm sorry but I'm going to marry this other boy." I was telling that story to some friends at a party and my girlfriend at the time was like, "You have to tell that on stage. It's a very funny story," and I was like, "Oh, I hadn't even thought about that."
The example on this album is a story about my girlfriend doing a very funny, charming thing, as a joke on me. I remember thinking it was a great thing and holding it in my head and telling my friends and they being charmed by my girlfriend's perspective and actions. But I never thought to take it on stage until I told it on a podcast. Then I ended up telling it extemporaneously at a UCB show where you were supposed to not prepare material. You got a word prompt and I got one that reminded of it and then I realized, "Oh, that's a bit."
So, I have the dual thing. I don't always recognize when something's a bit and also, I can't turn off my brain! So it's kind of the worst of both worlds!