Stoic Lessons From The Odyssey w/ Ryan Holiday artwork

Stoic Lessons From The Odyssey w/ Ryan Holiday

The Rich Roll Podcast

August 3, 2026

Ryan Holiday is a bestselling author and a leading voice in modern Stoicism. This conversation explores Christopher Nolan's interpretation of Homer's Odyssey and the moral truths the poem was built to transmit.
Speakers: Rich Roll, Ryan Holiday
**Rich Roll** (0:00)
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Ryan, you are an expert on Stoicism and Greek philosophy. This is your moment. Christopher Nolan's The Odyssey. The Odyssey.

**Ryan Holiday** (1:36)
The Odyssey. Possibly the most anticipated movie of the year.

**Rich Roll** (1:40)
Already breaking ticket sales records. The story's endured for 3,000 years.

**SPEAKER_3** (1:45)
It's resonated with every generation.

**Ryan Holiday** (1:47)
Each generation reads The Odyssey differently than the generation before. The more you know about it, the more it operates on all these other levels. The whole point is that the Odyssey is complicated and it's hard to know who the good guy is. Odysseus in his Odyssey is a reflection of the human undergoing any kind of ordeal. He's both like the best and the worst. We contain that in ourselves too. That is the point of the Odyssey.
Are we cool with spoilers in this?

**Rich Roll** (2:20)
Yeah, I think so. Yeah.

**Ryan Holiday** (2:21)
Okay, the catch should be out of the bag by now, 3,000 years later.

**Rich Roll** (2:28)
I'm super excited to talk to you, Ryan. You are well-known worldwide for being an expert on Stoicism and Greek philosophy. Generally, we're having a monoculture moment that you must be relishing, where everybody is celebrating this old poem by Dint of Christopher Nolan's, I'll say it right now, Masterpiece. I love the movie. I saw it a second time last night.
You have been posting lots of videos and this YouTube video with your thoughts on what we should understand from The Odyssey, what's important to understand. I thought it was an opportune moment to just get you on here and have you share your reflections on Homer's Odyssey, Nolan's Odyssey, and how you're synthesizing this and interpreting it. For us. So first of all, I guess, how did you like the movie?

**Ryan Holiday** (3:24)
Well, I should stipulate here that I know it not as a classicist. I don't speak Greek or Latin. I know it as a regular person who has been fascinated with it, who studied it with its connection to Stoic and other forms of philosophy. Then my nine-year-old son got very excited about it. So I've sort of hit it from a bunch of different angles, but all of these angles much closer to a lay person than, say, like a translator's, right? So I do feel like I was able to enjoy the movie on a couple of different levels. And I really did enjoy the movie. I thought it was spectacular. I have some some quibbles here or there. But I think what we have to understand is the Odyssey, like all of the other Greek myths, was both a form of art. It's beautiful language, it's evocative, it's entertaining, it's all this. But then it was there in a way that we don't always understand art and entertainment to be today, which was a means of communicating ancient wisdom and timeless moral truths. So, you know, like if you watch a Greek play, you know, like Shakespeare, all the actors are men, but they're not really like they wear these masks. The acting is not the key in a Greek play or in a Greek tragedy.
It's the language, it's the lessons, it's the lines. And so I think the problem is we don't always understand art as being that. Like, you know, most fiction today is almost like, I want to say it's almost amoral and that it's like designed not to teach moral truth, but to question moral truths. And so if we understand the Odyssey as being this sort of story that was told and retold and retold for thousands of years, each generation sort of thinking about the same truths, but bringing their own interpretation and understanding of them, their understanding of Odysseus, for instance, the understanding of Odysseus' dilemmas throughout the play, then you should actually appreciate both what Nolan did in telling it his own way, and you should appreciate the arguments over it, right? Like that is the point, is that each generation reads the Odyssey differently than the generation before. And then each new medium that we're able to tell it in, including going from an oral tradition to a written tradition, is going to fundamentally change. The medium is the message.

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