4.4 • 1.1K Ratings
🗓️ 24 October 2025
⏱️ 76 minutes
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| 0:00.0 | Ellie in a lot of ways is sort of, you could describe it as like it's the archetypal American |
| 0:04.5 | city. Here's the largest significance of What's Upon a Time at Hollywood, or my view of it, which is |
| 0:08.5 | it captures a time and place that was absolutely critical to the evolution of modern America. |
| 0:13.0 | The reaction from the audience is extreme laughter. You are laughing during the most island |
| 0:18.1 | sequence for 20 minutes. Some movies don't just entertain. |
| 0:22.5 | They help explain America. |
| 0:24.4 | On this episode of moderating the situation, |
| 0:26.6 | Catherine Boyle and I are joined by A16Z general partner Mark Andresen |
| 0:30.2 | to talk about the films that capture the country's turning points, |
| 0:33.4 | from Hollywood's golden age to the counterculture, |
| 0:36.0 | from the comedies we could once make to the stories that still define us. |
| 0:39.6 | We look at how different directors across decades have reflected and sometimes predicted where America was heading and what its art reveals about the culture behind it. |
| 0:47.9 | Let's get into it. |
| 0:51.4 | Well, excited to have the Modern Situation crew back for another episode on movies. Mark, thanks for joining again. Yes, excited. So we wanted to go deeper into some of our favorite movies. Mark, I know from watching movies with you that one of your genres you enjoy is movies about Hollywood. And so we want to start with Once Upon a Time in Hollywood. Why don't you talk about what's so remarkable about that or why you wanted to talk about it? The reason I was about Hollywood, I mean, they tend to be very entertaining because of course the people who make movies about Hollywood are from Hollywood. They know where all the bodies are buried and they tend to put them all in the movies. And so they're, you know, oh, run up spectacular Hollywood movies. So for people who haven't seen, I would recommend Mahalo Drive. It's one of Eric's favorites. |
| 2:04.4 | That name is Robert. popular Hollywood movies. So for people who haven't seen, I would recommend Mahalo Drive. It's one of Eric's favorites. And then the player, which also is an all-time one. There's a bunch, of course, famous ones like Sunset Boulevard. But, you know, the iconic Hollywood movie, you know, now is once upon a time in Hollywood, you know, like Quentin Tarantino. And so the reason I like Hollywood movies is because, you know, there are a handful of cities that have a claim to be like the ultimate American city. And, you know, New York City is one of those, you know, I think, you know, San Francisco in some ways, you know, where we are is. But L.A. and Las Vegas also put it in the list. By the way, for Las Vegas, see Bugsie. I'll talk about that another time, but that's the iconic Vegas movie. But Ellie, in a lot of ways, you could describe it as like it's the archetypal American city. |
| 2:18.0 | Literally... By the way, for Las Vegas, see Bugsie. I'll talk about that another time, but that's the iconic Vegas movie. But L.A. in a lot of ways, you could describe it as like it's the archetypal American city. Literally, it's a, there's a great book we can put in the nose called Thinking Bag where it goes to actually the creation of the city of Los Angeles. And basically, like, Los Angeles, you could argue is the ultimate Arab American city because it was the ultimate fake it until you make it thing. like it wasit-it-thing. Like, it was the thoroughness of cities. |
| 2:35.1 | And very specifically, like, it was desert. Like, there was absolutely nothing in L.A. And then, you know, literally it was like a land development deal by a bunch of wealthy families in late 1800s. And they literally placed newspaper ads in Eastern newspapers. You know, this is before, you know, photography made it into newspapers. And so like, you know, when there was like a picture of something, a newspaper would be a drawing. |
| 2:34.2 | And so they would list land know, when there was like a picture of something, a newspaper would be a drawing. |
| 2:35.7 | And so they would list land plots for sale of Los Angeles. And they would have, like, line drawings of like, you know, orchards and like, you know, beautiful everything's green and poultrys. And then, you know, people would like buy the land, move across country and discover that it was just like blasted out desert. and then, you know, they famously created the city. |
| 2:49.3 | They carved it out of the desert. |
| 2:50.4 | And then, you know, it's a famous saga of how they went to get the water, |
| 2:53.1 | which turned into another great L.A. movie, Chinatown. And, you know, as you'd expect, you know, Hollywood kind of goes for a certain interpretation of history. And so it, you know, sort of painted in retrospect as like a purely evil activity. But, you know, there's actually like a very kind of straightforward reading which was like this is what was actually required to create a city. It wasn't as black and white as sort of the Hollywood history has it It was a more complex story But still, you know, very, very interesting, amazing story And you know, cities like Los Angeles are created every day, so, you know, that's a pretty big deal. So anyway, like movies about L.A., I think when they reach the level of capital A art, you know, they become movies about America. And so it's like a great test bed or a great subject, you know, sort of great lens through which to look at the history of America. And once upon a time on Hollywood is, I would say, one of the top movies along that theme. Let me start by saying, if anybody watched this hasn't seen Once Upon a Time on Hollywood, pause the podcast immediately. Go watch the movie. And then come back because we're going to spoil the shit on it. And it's tremendously fun to watch if you haven't read about it. By the way, I'd also say, like, it's a tremendously entertaining movie. Like, it's one of the most entertaining Poff-for-Pond movies. You know, it's like infinitely rewatchable. The cast is ridiculous. Every frame of the thing is amazing. So it's also a very fun movie. |
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