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AI Chatbots Are Like Observational Comics | Drew Breunig

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As a child of the 90s, I was raised watching observational comedy specials. Seinfeld, Carlin, Hedberg, Rock, Poundstone, Izzard… I watched it all. It wasn’t just the jokes I enjoyed. I was in awe of each comedian’s ability to fully engage you (and the entire audience), managing your expectations and attention. By themselves, alone on stage. By just talking. You don’t notice how much work they’re doing – they make it appear effortless. But a decade later, I caught a post on Twitter from Seinfeld saying he’d be trying out new material at a Manhattan club that night. I quickly snagged tickets and two hours later we watched him walk on stage during a Wednesday open mic. Watching Seinfeld try out new material gives you a peak behind the curtain. Before each bit he’d lift up his notepad, push up his glasses, hunch over, and quietly read the note aloud to himself: “Five hour energy drink… five hours is a weird amount of time.” Every time he read his notes, you’d cringe a bit. “C’mon Jerry, th

Apr 8, 2025 AI PERFORMANCE COMEDY AI Chatbots Are Like Observational Comics Both lose their magic when talking about something you know As a child of the 90s, I was raised watching observational comedy specials. Seinfeld, Carlin, Hedberg, Rock, Poundstone, Izzard… I watched it all. It wasn’t just the jokes I enjoyed. I was in awe of each comedian’s ability to fully engage you (and the entire audience), managing your expectations and attention. By themselves, alone on stage. By just talking . You don’t notice how much work they’re doing – they make it appear effortless . But a decade later, I c

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