Old School with Shilo Brooks
The Free Press
Episode: George Orwell’s Lessons on the Class Divide
Date: November 20, 2025
Guest: Rob Henderson

Episode Overview

In this insightful episode of Old School, host Shilo Brooks sits down with author Rob Henderson to explore George Orwell’s Down and Out in Paris and London (1933). They discuss how Orwell’s first book, a blend of memoir and journalism chronicling his time among the poor in two great European cities, inspired Henderson and resonates in the context of today’s class divides. Themes include the complex psychology of poverty, class stratification, the moral power of literature, and the important differences between seeing and living poverty.

Key Discussion Points & Insights

Why Down and Out in Paris and London—Orwell’s Lesser-Known Work?

• Orwell, born Eric Blair, adopted the pen name to spare his family “embarrassment” as he lived among society’s downtrodden. (01:29)
• Henderson read Down and Out at 15, relating deeply from his own impoverished background. He found it revelatory:

  “I think I had just read Animal Farm for class... passing through the school library, I saw Down and Out... Oh, this is a nonfiction book about his own personal experiences and his brushes with poverty... I was in pretty rough shape ...and I read the book in maybe three or four days.” (01:50–03:15)

The Book’s Structure: Memoir, Journalism, & Social Experiment

• The first half is set in Paris, depicting grueling menial work in a hotel kitchen; the second, in London, immerses Orwell in the life of a tramp.
• Brooks highlights core figures: Boris (the eternally optimistic Russian), Paddy (the resigned Englishman), and Bozo (the reflective, artistic tramp).
• Quote:

  "[Orwell] was exploring the pathologies of poverty by way of trying to live the life, but also by isolating different aspects of it and different aspects of the psychology of poverty through the exploration of these characters..." (06:24)

The Subjectivity of Poverty & the Pitfalls of "Slum Tourism"

• Henderson praises Orwell for avoiding ideological preconceptions—three men, similar conditions, very different responses.
• Poverty is personal:

  “Each person experiences poverty in a different way, that you can’t make these blanket statements about the poor... if you put 10 people in a very impoverished environment, you’ll have 10 different unique stories.” (08:18)

Self-Sabotage, Opportunity, and Class Psychology

• Boris, always “one day from being saved,” exemplifies self-sabotage—something both Henderson and Brooks witness among the poor in their own lives.
• Quote:

  “There’s a fear, I think, of success… If you succeed and then come back down, there will be a kind of humiliation or a disgrace. Whereas if you continue at the place that you’re at, you never have to worry...” (11:05)

Can the Privileged Portray Poverty Authentically?

• Discusses the modern critique that only the lived can write the life—e.g., can a privileged person write about the poor?
• Henderson:

  “Whereas, you know, if Boris had written this book or a similar account, probably fewer people would have taken it seriously. For better or worse.” (15:03)

• Brooks powerfully defends literature’s imaginative power:

  “To say that Orwell doesn’t have access to poor people because he wasn’t one, is to deny the power of the imagination, to give you some transformative insight into the life of another...” (16:01)

The Social Effects of Class and Respectability

• Orwell’s brief privilege—e.g., being treated differently at a shelter—shows “respectability is a resource.” (17:20)
• Invisible social cues dictate treatment, even among the poor.

The Contrasts Between Paris & London: The Many Faces of Poverty

• Paris: punishing, unending labor—the working poor.
• London: enforced idleness, boredom, and dependence—absolute poverty.
  “In Paris, Orwell is... living on the margins... In London, it’s much more unsheltered poverty...” (21:09)

The Work Ethic and Stigma

• Orwell insists most tramps “do want to work,” contrary to social stereotypes.

  “My suspicion is that you probably didn’t have to make that many mistakes to be down and out... The people who were poor... did want to work. They were different. It was a different time.” (22:49)

Bozo: Educated Reflection vs. Degradation

• Bozo, a kind of street philosopher-artist, is an exception—poverty does not embitter him.
• Brooks explores the difference between educated poverty (e.g., Bozo, Socrates) and uneducated poverty (Boris, Paddy). Reflection makes suffering manageable, even meaningful. (24:29–26:36)

Class Segregation, “Luxury Beliefs,” and Contemporary Parallels

• Orwell and Henderson swapped perspectives: Orwell, rich-to-poor; Henderson, poor-to-rich, “reverse anthropologists,” each illuminating class for their own and the other’s social classes. (42:24)
• Henderson coins “luxury beliefs”—ideas fashionable among the elite that aren’t feasible for the poor (e.g., family structure, criminal justice reforms).

  “...the confidence that you know what to do for everyone else seems to either sort of maintain itself or even increase... you don’t know these people, you don’t spend time around them, but you have an idea of how they should be living...” (34:43)

The Hidden Consolation of Hitting Rock Bottom

• Orwell writes that there is “almost a pleasure at knowing yourself at last genuinely down and out”—relief in having one’s worst fear realized and survived.

  “You don’t have to make choices anymore. Your choices are made for you... You just have to think about survival.” (31:21)

Sex, Gender, and the Demography of Poverty

• Poverty is overwhelmingly male—a theme Orwell foregrounds.

  “It’s a psychological feature of poverty that I think a lot of folks aren’t thinking about.” (44:36)

• Henderson adds, “He says that might be even more humiliating in some ways, to be unwanted as a person.” (46:33)

Notable Quotes & Memorable Moments

• “You have talked so often of going to the dogs and well, here are the dogs and you have reached them and you can stand it. It takes off a lot of anxiety.” —George Orwell, quoted by Henderson (29:26)
• “To say that Orwell doesn’t have access to poor people because he wasn’t one, is to deny the power of the imagination.” —Shilo Brooks (16:01)
• “Respectability is a kind of a resource on its own.” —Rob Henderson (17:20)
• “If you put ten people in a very impoverished environment, you’ll have ten unique stories.” —Rob Henderson (08:18)
• “The confidence that you know what to do for everyone else seems to... maintain itself or even increase.” —Rob Henderson (34:43)
• “What’s the best thing about being poor? You don’t have to think as deeply about your future.” —Rob Henderson (57:26)
• On humor: “The thought of not being poor made me very patriotic.” —George Orwell, quoted by Henderson (54:02)

Timestamps for Key Segments

• Orwell’s Background & Book’s Impact: 01:29–03:49
• Plot and Characters Breakdown: 03:49–08:18
• Subjectivity & Authenticity of Orwell’s Experiment: 08:18–16:01
• Class, Imagination, and Literature’s Power: 16:01–17:20
• Hotel Life and Social Dynamics: 17:20–21:09
• Paris vs. London—Two Kinds of Poverty: 21:09–22:49
• Reflective Poverty (Bozo) vs. Degraded Poverty (Boris, Paddy): 24:29–27:52
• Contemporary Class Divide & Luxury Beliefs: 34:43–36:48, 59:18–60:40
• Male Poverty & Loneliness: 44:36–48:28
• Comic Relief—Orwell’s Humor: 54:02–56:28
• Lightning Round—Reflections on Being Poor: 56:59–59:18
• Who is the Book For?: 50:47–51:40

Who Is This Book For?

• Henderson: Those feeling lost, impoverished, or seeking to make sense of hardship. It serves as “medicine” for those navigating the margins, showing life can be made meaningful and even transcended. (50:47–51:40)

Closing Thoughts

Down and Out in Paris and London stands out for its humanism, its unpretentious narrative, and its unwillingness to impose ideology, according to both Brooks and Henderson. It remains relevant as a meditation on class, aspiration, humiliation, and the vital, dangerous gap of understanding separating the classes in both Orwell’s Britain and today’s America.

Further Reading Recommendations

• By Orwell:
  • Down and Out in Paris and London (1933)
  • The Road to Wigan Pier (1937)

    “It’s a more mature kind of book... two pieces of this puzzle of at least Orwell’s account of poverty.” (60:48–61:40)

• Rob Henderson’s Memoir:
  • Troubled

End of Summary.