WEBVTT

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Welcome to the Deep Dive. This is where we take

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a whole stack of sources, pull out the key knowledge

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you need, and hopefully give you that edge of

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being, well, instantly up to speed. And today

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we're diving into someone who, yeah, really defies

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easy labels, Brent Weinbach. Exactly. We're looking

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at a comedian, but also a professional jazz pianist,

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and an award -winning screenwriter, and a director

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of like... Cult web stuff. It's a lot. It really

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is. It's not just, you know, versatility. It

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feels more like synthesis. The sources we've

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got lay out this incredibly varied path. Live

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shows, music analysis, digital media. And how

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it all connects. That's the fascinating bit.

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How these threads weave together. Yeah. So our

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source material today, it's pretty comprehensive.

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It covers his evolution from his early days,

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the academic stuff, music, right up to his recognition

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in comedy and surprisingly, film. Right. So the

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mission for you listening is really to break

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down this very experimental, very multidisciplinary

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career. We want to figure out how that deep discipline,

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like being a master pianist, somehow fuels the

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pan -tracked kind of wild freedom in his comedy.

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It's a cool puzzle. Okay, so let's lay down the

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basics first. The core identity points. Source

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confirms. American, stand -up comedian, actor,

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director, pianist. Based in LA. But roots in

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Berkeley. You see Berkeley grad. Which, you know,

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that intellectual background, I think it's pretty

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key to understanding how he structures the absurdity

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later on. It's not just random. Definitely. Okay,

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let's get into that. Part one, the foundation.

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All right, let's unpack his artistic DNA. The

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sources keep coming back to three words, experimental,

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abstract, and deadpan. That's the core aesthetic.

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And that combination, it's, well, it's not typical,

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especially not in mainstream comedy. Deadpan

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usually goes with, like, observational stuff.

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Overgrounded things. Yeah, or social commentary.

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So how does that work? How does a super deadpan

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delivery actually help when the material itself

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is totally abstract and weird? Well, think about

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the function of the deadpan there. If the idea

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is already surreal, like that multi -level marketing

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plan for dating he did on Conan. Right. Or, you

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know, demonstrating some totally fake, complex

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drumming technique. The deadpan delivery, that

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complete seriousness, it kind of has to anchor

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it. Otherwise, it just floats away. It's control.

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The ideas are way out there. Makes the audience

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go, wait, what? Is this serious? But the delivery?

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Super controlled. No winking. Exactly. He commits

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fully to the premise no matter how absurd. And

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that commitment, that's what takes it from just,

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you know, being weird to being something more

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like conceptual art. And then control that discipline.

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It seems like it leads right back to his background,

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doesn't it? This style wasn't just cooked up

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out of nowhere. No, absolutely not. It feels

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like it grew out of some real structure, some

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rigor. Totally. Connecting the dots. We mentioned

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UC Berkeley. That points to, you know, intellectual

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curiosity, analytical thinking. But maybe even

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more revealing are those jobs he had before comedy

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took over full time. He was a professional jazz

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pianist and this one's kind of surprising, a

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substitute teacher. OK, let's pause on the jazz

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pianist thing, because I feel like that's huge

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for his comedy structure. requires insane technical

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skill, right? Rhythm, structure, theory. Oh,

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completely. You have to master all the rules,

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scales, harmony, just perfectly. So you can then

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break them convincingly. Yeah. Improvise. Exactly.

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And that discipline, you can almost map it onto

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his comedic timing. For him, a joke isn't just

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set up punchline. It feels more composed, like

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music. Think about tempo, cadence. And silence.

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The pauses. Yes, silence. The rest in music.

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It builds tension, anticipation. And in deadpan

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comedy, that long pause before the final weird

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line, that's everything. It stops it from just

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being noise. He uses silence like negative space

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in art. It makes the words hit harder. And improvisation,

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too. Central to jazz, central to stand -up. You

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follow the moment, you pivot, but you keep the

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structure intact while exploring something new.

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That training in structured improv. Priceless.

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Okay, then the substitute teacher part. Seems

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like a total left turn, but maybe not. Well,

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think about it. It's like an observation lab

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and crowd control boot camp rolled into one.

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Yeah, okay. Seriously. Subs have to think fast,

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engage the room immediately, and teenagers. Toughest

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crowd. Cynical. Plus, you're just constantly

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observing human behavior, little awkward moments,

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bureaucratic stuff. Which he then twists into

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his abstract concepts, takes the mundane and

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makes it... Bizarre. Precisely. We should also

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mention, just for context, his identity. Sources

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note he's half Filipino and half Jewish. And

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creativity seems to run in the family. His sister,

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Laura Weinbach, she's in that band Foxtails Brigade.

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Oh, right. And her husband, his brother -in -law,

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Anton Patzner. So there's this, like, lineage

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of artistry there. Music, performance. It's in

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the blood, maybe. Okay, so when we talk about

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Brent Weinbach getting recognized, there's one

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award we absolutely have to start with. It feels

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like it defines his whole approach. Yeah. The

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Andy Kaufman Award. Yes, this is so important

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because the Kaufman Award, it's not about, you

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know, selling out arenas or being super mainstream.

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No. It's about intellectual integrity, conceptual

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stuff. The source says it flat out. It recognizes

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innovation in stand -up comedy. So what does

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winning that actually mean for him? For you,

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the listener, think about it. It means the comedy

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world, or at least a significant part of it,

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values him for pushing boundaries, for the ideas.

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Yeah, not just for, like, the laugh per minute

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ratio. It puts him in that Kaufman lineage. Artists

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who messed with the form itself blurred the lines

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between performance and reality. Kaufman often

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made people feel uncomfortable, confused, not

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just amused. Right. Traditional stand -up wants

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the laugh. Kaufman style comedy often aims for

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something else using the stand up format. And

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Winebox somehow does that while still being genuinely

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funny. It's a tricky balance. So he's seen as

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this like conceptual architect in comedy. building

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weird structures instead of just telling jokes.

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But if his stuff is so out there, how does he

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do in normal competitive settings? That's the

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interesting thing. He's got the conceptual chops,

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but he also proved he could deliver in the traditional

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arenas. He was a finalist in the 2008 San Francisco

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Comedy Competition. Which is notoriously difficult.

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You need consistency. You need to connect with

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maybe resistant crowds. Exactly. The fact that

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his abstract style worked there shows that the

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underlying craft, the timing, the discipline

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we talked about, it's soft. It makes the weirdness

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land. He connects while challenging expectations.

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Okay, so that skill lets his unique style travel.

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He wasn't just stuck in one niche scene. No,

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definitely toured quite a bit. The sources list

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appearances at major festivals, Coachella, SF

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Sketch Fest, Bumbershoot, just for laughs. Coachella's

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interesting. Huge, diverse crowd. Means his kind

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of different voice was seen as like essential

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to that modern festival mix. People wanted something

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unexpected. And this is where it gets really

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fascinating, the bridge to the mainstream. Even

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with this commitment to the experimental, he

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got significant exposure. Yeah, he brought the

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abstract stuff to late night TV, appeared on

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Lopez Tonight and notably Conan. And that Conan

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set title you mentioned earlier, The Way to a

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Man's Heart, is through my multi -level marketing

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plan. That's just peak Weinbach. Taking dry corporate

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language. We're replying it to something intimate

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and absurd like dating. The Deadpan just sells

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the ridiculousness of pitching romance like Amway.

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That blend, mundane commercial speak, meets high

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concept surrealism. That's his zone. And even

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before the internet really blew up for comics,

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he was part of that whole comedians of comedy

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tour group. Right. That was huge for defining

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alternative comedy in the 2000s. Put him right

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alongside others who were finding humor outside

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the standard club formula, cemented his place

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as an innovator. OK, so if the stage is where

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he refined the timing, the Internet feels like

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where he built these lasting weird little worlds

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and characters. You've got to spend some real

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time on him as a digital creator, starting with

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Poundhouse. Oh, yeah. Poundhouse ran for, what,

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10 years, 2013 to 2023. That's basically forever

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in Internet time. Totally. And he was all over

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it. Co -creator, co -director, writer and playing

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Brent. With DJ Doug Penn. It perfectly captured

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that abstract, character -based style online.

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Just two housemates, mundane stuff, but pushed

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to extremes through this weird, looping, almost

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reality TV parody lens. And it got noticed, right?

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It wasn't just a fringe thing. No, it got critical

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recognition, nominated for a Streamy Award, which

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is pretty major for something that often just

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went for pure, sustained absurdity over, you

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know, neat little stories. He seemed to get...

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really early on, how well that kind of abstract,

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concept -heavy humor plays online. Short bursts,

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minimal context needed. Definitely. And that

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understanding led to those other viral video

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hits, the ones that are just pure, concentrated,

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wind -back online. Yeah, let's talk about those.

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The source names Gangster Party Line, Mind Jack,

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and Ultimate Drumming Technique. We should probably

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unpack those a bit for the listener. Okay, Ultimate

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Drumming Technique. Ties right back to the music

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background, obviously. It looks like one of those

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instructional videos. Right. Super serious. But

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instead of teaching anything useful, he demonstrates

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these increasingly bizarre, totally pointless

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physical movements with absolute dead serious

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commitment. It's like he's parodying the whole

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idea of technical mastery, which he actually

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has, by focusing on the most meaningless, awkward,

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physical parts of performance. It's physical

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comedy, but you have to think about it. Exactly.

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And then... Gangster party line. What a concept.

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Yeah. It mashes up that hyper -stylized language

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from gangster movies or rap, you know, really

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specific slang and tone. With the most boring,

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mundane thing possible, like a phone chat line

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or a customer service call center script. The

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clash is the joke. Taking a dramatic trope and

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forcing it into this rigid administrative box,

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these videos weren't really about set -up punchline

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laughs, more like creating this little intellectual,

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huh? moment that makes you want to share it.

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That success with short form conceptual stuff

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online definitely led to writing gigs in traditional

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media, but ones that fit his style. Like he wrote

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for the Eric Andre show in 2015. Which makes

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total sense. Another show built on surreal, confrontational,

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structured chaos. If you can write for Poundhouse

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and Eric Andre, you've mastered a certain kind

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of controlled absurdity. But he didn't just stay

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with sketches and digital shorts. The sources

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show him taking those writing and directing skills

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into like actual film recognition. Yeah, this

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is a big shift. In 2022, he won Best Screenplay

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at the Los Angeles International Film Festival.

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The Spirit of Los Angeles Award shared with Bruno

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Cofield Galeano. Wow. OK, so moving from co -directing

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a cult web series to winning a screenplay award

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that shows the concepts can hold up in a longer

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structured narrative. It's not just quick hits.

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Right. It takes a different kind of discipline

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to manage a whole plot compared to a sketch.

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Shows real range. And he's still involved in

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that world. There's an upcoming project, False

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Awakenings, where he has a story by credit. So

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he's still developing these big conceptual frameworks,

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whether it's for a one minute video or a full

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movie. OK, we keep circling back to the music.

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Brent Weinbach, professional jazz pianist. Let's

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dig into how that actually shows up in his comedy

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albums, because they are just, you know, recordings

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of his standup sets. No, not usually. They're

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often more layered, conceptual. The blending

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started early. His first one. Tales from the

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Brownside from 2004. The source mentions it was

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specifically inspired by Joe Frank. Ah, Joe Frank.

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Okay, for listeners who might not know him. Legendary

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radio guy known for these really atmospheric,

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sometimes dark narrative pieces, mixed spoken

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word, sound effects, music. Right. So that connection

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right away tells you Winebox thinking about atmosphere,

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storytelling, the whole soundscape. Yeah. The

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album as an experience, not just a string of

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jokes. Then his second album, The Night Shift

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2009, really seemed to formalize that mix. The

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source says it's a blend of live comedy, studio

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recordings and original music. Yeah. The music

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isn't just background filler. It's part of the

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composition, setting a mood, maybe playing against

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the spoken words. It sounds like he's using sound

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design and music as extra tools in his comedy

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toolkit, like rhythm and melody, creating tension

00:12:17.750 --> 00:12:20.090
and release alongside the words. Totally. And

00:12:20.090 --> 00:12:21.950
you see that continue in later albums, too, like

00:12:21.950 --> 00:12:25.129
Mostly Live 2012. And the title of Appealing

00:12:25.129 --> 00:12:28.470
to the Mainstream 2017 feels like classic Weinbach

00:12:28.470 --> 00:12:30.529
commentary. Yeah. And then there's the curveball,

00:12:30.649 --> 00:12:33.029
the one only a skilled pianist with his specific

00:12:33.029 --> 00:12:35.970
sense of humor could throw, the 2017 album Christmas

00:12:35.970 --> 00:12:38.750
Piano. It's just perfect. Such a great piece

00:12:38.750 --> 00:12:42.190
of comedic juxtaposition. Because on the surface,

00:12:42.429 --> 00:12:45.669
it's totally straight. A talented musician playing

00:12:45.669 --> 00:12:48.309
Christmas standards. But knowing his whole deal,

00:12:48.450 --> 00:12:51.169
the experimental abstract stuff, just releasing

00:12:51.169 --> 00:12:54.330
a completely normal Christmas Piano album, feels

00:12:54.330 --> 00:12:56.429
like the ultimate deadpan move. Is he making

00:12:56.429 --> 00:12:58.970
fun of it? Is he genuinely just playing music

00:12:58.970 --> 00:13:01.049
he likes? You can't quite tell. And that ambiguity,

00:13:01.269 --> 00:13:04.129
that's pure Weinbach, using his actual skill

00:13:04.129 --> 00:13:07.090
to make something so unexpectedly normal that

00:13:07.090 --> 00:13:09.049
that becomes the radical funny thing. Beyond

00:13:09.049 --> 00:13:11.129
the albums, though, he puts that deep musical

00:13:11.129 --> 00:13:14.049
knowledge into this other really specific long

00:13:14.049 --> 00:13:16.529
-running project, the Legacy Music Hour podcast.

00:13:17.009 --> 00:13:19.610
Right. Started way back in 2010. This isn't just

00:13:19.610 --> 00:13:21.490
a side hobby. It's a serious long -term thing.

00:13:21.629 --> 00:13:24.269
He hosts it with Rob F. Switch. And the topic

00:13:24.269 --> 00:13:27.960
is super niche. Retro video game music. Specifically

00:13:27.960 --> 00:13:31.679
80s and 90s stuff. NES, SNES, Genesis. But it's

00:13:31.679 --> 00:13:34.019
not just nostalgia, is it? He's actually analyzing

00:13:34.019 --> 00:13:36.600
this music, applying real music theory, harmony,

00:13:36.679 --> 00:13:39.240
structure, orchestration to chiptunes. Exactly.

00:13:39.240 --> 00:13:40.799
Which is fascinating because, you know, people

00:13:40.799 --> 00:13:43.000
often dismiss that stuff as just bleeps and bloops.

00:13:43.120 --> 00:13:45.419
But he's talking about composers working under

00:13:45.419 --> 00:13:48.679
extreme limitations, only a few sound channels

00:13:48.679 --> 00:13:51.559
on an NES, right? Yeah. So they had to be incredibly

00:13:51.559 --> 00:13:54.460
clever. Weinbach gives that ingenuity serious,

00:13:54.580 --> 00:13:57.350
informed analysis like you'd hear. for classical

00:13:57.350 --> 00:14:00.269
music or jazz he treats the loops the melodies

00:14:00.269 --> 00:14:03.350
the counterpoint as real compositional choices

00:14:03.350 --> 00:14:06.490
it's like another extension of his identity The

00:14:06.490 --> 00:14:08.789
technical musician who thinks all music is worth

00:14:08.789 --> 00:14:11.809
deep study, no matter where it comes from. And

00:14:11.809 --> 00:14:13.809
that podcast has found its audience. It's a fixture.

00:14:13.970 --> 00:14:16.289
The source mentions crossovers with other pods

00:14:16.289 --> 00:14:18.750
like Laser Time. Yeah. Shows he can build a community

00:14:18.750 --> 00:14:21.090
around this very specific passion, connecting

00:14:21.090 --> 00:14:24.830
music theory, nostalgia and gaming. OK, let's

00:14:24.830 --> 00:14:26.529
switch gears slightly to Weinbach, the actor.

00:14:26.669 --> 00:14:28.289
His own stuff is very self -driven, obviously.

00:14:28.490 --> 00:14:32.009
But how do other directors use his unique, controlled

00:14:32.009 --> 00:14:34.919
vibe? Started small, looks like. A waiter in

00:14:34.919 --> 00:14:37.480
Medicine for Melancholy back in 2008. Yeah, a

00:14:37.480 --> 00:14:39.879
small start, but it opened the door to this really

00:14:39.879 --> 00:14:42.840
varied mix of guest spots. And looking at the

00:14:42.840 --> 00:14:44.960
specific roles, you can really see how casting

00:14:44.960 --> 00:14:47.740
directors deploy that deadpan, slightly off energy

00:14:47.740 --> 00:14:52.259
he has. Like, OK, in 2013, he's Greg in an episode

00:14:52.259 --> 00:14:54.919
of The Middle, which is, you know, a pretty standard

00:14:54.919 --> 00:14:57.480
network family sitcom. Yeah. Very different world

00:14:57.480 --> 00:15:00.350
from abstract comedy. Right. But casting him,

00:15:00.389 --> 00:15:02.690
even in a small role like that, adds this little

00:15:02.690 --> 00:15:05.809
touch of unexpectedness. His presence, even when

00:15:05.809 --> 00:15:07.889
controlled, just feels a bit different. Makes

00:15:07.889 --> 00:15:09.809
the character memorable. You see him fitting

00:15:09.809 --> 00:15:11.870
right into those cable comedies that really lean

00:15:11.870 --> 00:15:15.149
into absurdity. Like Corporate in 2018. He played

00:15:15.149 --> 00:15:17.549
Walter in the Casual Friday episode. And Corporate's

00:15:17.549 --> 00:15:19.830
whole thing is satirizing office weirdness, right?

00:15:19.970 --> 00:15:23.250
So his kind of controlled, cynical deadpan is

00:15:23.250 --> 00:15:25.970
a perfect match for that show's tone. And he

00:15:25.970 --> 00:15:28.129
was definitely part of that whole alternative

00:15:28.129 --> 00:15:31.090
comedy TV scene that embraced the weird. Oh,

00:15:31.090 --> 00:15:34.070
yeah. Multiple spots on Comedy Bang. Bang. Between

00:15:34.070 --> 00:15:36.409
2013 and 15. Played two different characters,

00:15:36.629 --> 00:15:40.059
Mailman and Carla Smencia. Comedy Bang. Bang.

00:15:40.399 --> 00:15:42.779
It's all about improv and characters pushed to

00:15:42.779 --> 00:15:45.480
the max. So, yeah, natural place for him. And

00:15:45.480 --> 00:15:47.960
working with Tim and Eric, he was Brett, young

00:15:47.960 --> 00:15:50.200
intern, in that Tim and Eric's Bedtime Stories

00:15:50.200 --> 00:15:53.840
episode, The Endorsement, in 2014. Being in their

00:15:53.840 --> 00:15:56.059
world basically confirms you're the go -to person

00:15:56.059 --> 00:15:58.759
when a scene needs perfectly delivered, slightly

00:15:58.759 --> 00:16:01.679
uncomfortable, controlled weirdness. He also

00:16:01.679 --> 00:16:04.159
did a few episodes of another period in 2015

00:16:04.159 --> 00:16:07.460
as Scoops LaPoo. He seems to get cast as characters

00:16:07.460 --> 00:16:11.049
with amazing names. Yeah, that helps. But it's

00:16:11.049 --> 00:16:13.090
not just live action. His voice is distinctive,

00:16:13.250 --> 00:16:15.570
too, and he's used it in animation. Right, the

00:16:15.570 --> 00:16:18.029
source list's voice work. He was bass, drum,

00:16:18.169 --> 00:16:20.769
and other voices on Adventure Time in 2015. Also

00:16:20.769 --> 00:16:23.429
did voices for Clarence in 2017, and more recently,

00:16:23.549 --> 00:16:26.110
Lee in an episode of Close Enough called Golden

00:16:26.110 --> 00:16:29.570
Gamer in 2020. Golden Gamer. Yeah. Okay, that

00:16:29.570 --> 00:16:32.669
brings us back again to his connection to gaming

00:16:32.669 --> 00:16:34.990
culture, which we talk about with the Legacy

00:16:34.990 --> 00:16:37.309
Music Hour. It's not just the podcast. No, it

00:16:37.309 --> 00:16:40.149
seems really authentic. comedy persona into that

00:16:40.149 --> 00:16:42.169
world too. He's done guest spots on Game Grumps,

00:16:42.210 --> 00:16:44.389
the huge web series. Yeah. What did he do there?

00:16:44.490 --> 00:16:46.929
Well, back in 2016, he was on providing this

00:16:46.929 --> 00:16:50.149
very Weinbach -esque commentary over an old game

00:16:50.149 --> 00:16:52.730
called Time Lord. Just a perfect mix of gaming

00:16:52.730 --> 00:16:55.429
knowledge and abstract riffing. And it wasn't

00:16:55.429 --> 00:16:57.889
a one -off thing. Apparently not. The sources

00:16:57.889 --> 00:17:01.049
show him appearing again in 2025 playing Gekibo.

00:17:01.889 --> 00:17:04.450
Kikisha boy, which, you know, coming back almost

00:17:04.450 --> 00:17:07.029
a decade later, it shows his presence in that

00:17:07.029 --> 00:17:10.170
digital gaming space is real and lasting. It's

00:17:10.170 --> 00:17:13.150
a continuous thread. Hashtag Hotech outro. Wow.

00:17:13.250 --> 00:17:15.009
OK, pulling back to try and wrap our heads around

00:17:15.009 --> 00:17:18.000
all this. What we've got is this picture of an

00:17:18.000 --> 00:17:20.299
artist who just fluidly moves between totally

00:17:20.299 --> 00:17:23.680
different worlds. Jazz piano, 8 -bit music, stand

00:17:23.680 --> 00:17:26.859
-up stages, feature film writing. Yeah, but while

00:17:26.859 --> 00:17:29.220
pivoting across all those media, he stays laser

00:17:29.220 --> 00:17:32.200
-focused on this really specific, singular, abstract

00:17:32.200 --> 00:17:34.599
kind of vision. It's impressive. The main threads

00:17:34.599 --> 00:17:36.779
seem clear. That foundation of discipline, the

00:17:36.779 --> 00:17:39.000
pianist, the Berkeley grad, then the commitment

00:17:39.000 --> 00:17:42.079
to experimental deadpan comedy, getting the nod

00:17:42.079 --> 00:17:43.859
from the Kauffman Award. And then seeing how

00:17:43.859 --> 00:17:45.930
that conceptual strength translates into... to

00:17:45.930 --> 00:17:48.309
directing and writing, getting web series nominated,

00:17:48.589 --> 00:17:51.109
winning screenplay awards. While also maintaining

00:17:51.109 --> 00:17:54.130
these deep dives into niche passions like the

00:17:54.130 --> 00:17:56.329
video game music podcast and staying connected

00:17:56.329 --> 00:17:58.890
to those cult digital communities like Game Grumps

00:17:58.890 --> 00:18:01.970
and Poundhouse, it's a lot to balance. So what

00:18:01.970 --> 00:18:04.470
here for you, the listener? It's really about

00:18:04.470 --> 00:18:07.069
innovation through maybe controlled abstraction.

00:18:07.569 --> 00:18:09.910
He's like a model for a certain kind of modern

00:18:09.910 --> 00:18:11.789
artist. Doesn't stick to one box, one genre.

00:18:11.990 --> 00:18:14.309
He uses all the channels available, live shows,

00:18:14.509 --> 00:18:17.230
web stuff, podcasts, film, whatever fits to get

00:18:17.230 --> 00:18:19.670
this unique vision out there. And he shows how

00:18:19.670 --> 00:18:22.369
mastering something really specific and technical

00:18:22.369 --> 00:18:25.789
like music theory or joke timing can actually

00:18:25.789 --> 00:18:29.490
unlock the most abstract kinds of creative freedom.

00:18:30.640 --> 00:18:32.359
rules lets you break them effectively. Right.

00:18:32.559 --> 00:18:34.859
Which leads us to that final thought to chew

00:18:34.859 --> 00:18:37.119
on, something connecting his path to maybe your

00:18:37.119 --> 00:18:39.700
own professional life. How does that intense,

00:18:39.859 --> 00:18:43.460
maybe even rigid discipline you need to master

00:18:43.460 --> 00:18:45.700
something like jazz piano, how does that same

00:18:45.700 --> 00:18:48.259
discipline fuel the absolute abstract freedom

00:18:48.259 --> 00:18:51.319
you need for award -winning experimental comedy?

00:18:51.710 --> 00:18:54.069
Yeah. What can you learn from that about blending

00:18:54.069 --> 00:18:56.150
your own skills? Maybe skills that seem contradictory,

00:18:56.450 --> 00:18:58.910
the structured stuff and the wild ideas. How

00:18:58.910 --> 00:19:01.430
do you mix those to do something genuinely new

00:19:01.430 --> 00:19:03.769
and versatile? Something to think about. We'll

00:19:03.769 --> 00:19:04.750
leave it there for this deep dive.
