Conan O’Brien Needs a Friend: Episode with Ron Chernow

Podcast Information:

• Title: Conan O’Brien Needs a Friend
• Host/Author: Team Coco & Earwolf
• Episode: Ron Chernow
• Release Date: June 5, 2025

Summary: In this enlightening episode of Conan O’Brien Needs a Friend, host Conan O’Brien sits down with Pulitzer Prize-winning biographer Ron Chernow to delve deep into Chernow’s latest work—a comprehensive biography of the illustrious American humorist, Mark Twain. The conversation navigates through Chernow's extensive career, the intricacies of Twain's life, and the broader implications of Twain's work in contemporary society.

Ron Chernow’s Biographical Journey

[01:19] Ron Chernow:
"Hello, my name is Ron Giorno, and I feel very, very warmly about anyone who has won the Mark Twain award for humor."

Chernow introduces himself with warmth, highlighting his admiration for Twain and Conan himself. Conan acknowledges his passion for history and expresses his admiration for Chernow's meticulous research, having read all of his biographies, including the new Mark Twain biography.

Exploring Alexander Hamilton and Lin-Manuel Miranda’s Adaptation

[03:09] Conan O'Brien:
"You start out by writing about JP Morgan and this great Gilded Age industrialist... and then you go back to the beginning, the source who's running finance in America."

Conan traces Chernow's biographical trajectory, noting how his interest in industrial titans like JP Morgan and Rockefeller led him back to foundational figures like Alexander Hamilton. This segues into a discussion about Chernow’s influence on Lin-Manuel Miranda's Hamilton.

[04:34] Ron Chernow:
"People always say to me... did you imagine as you were writing the book that it was going to end up as a hip hop musical? And I always say, I think the question answers itself."

Chernow recounts how Miranda approached him with the idea of adapting Hamilton into a hip-hop musical, leading to the groundbreaking Broadway phenomenon. He shares an anecdote about Miranda performing a condensed version of his book at his brownstone, foreshadowing the musical’s success.

Ulysses S. Grant: From Failure to Fame

[08:15] Ron Chernow:
"You have written about J.P. Morgan, Rockefeller... but writing about Ulysses S. Grant was something different."

The conversation shifts to Chernow's biography of Ulysses S. Grant, where he explores Grant's transformation from a struggling woodcutter to a celebrated Civil War general. Chernow emphasizes Grant's depiction of failure and resilience.

[10:16] Conan O'Brien:
"If you saw it in a movie, you'd say, well, we gotta fix that part... it's absolutely astounding."

Conan marvels at the rapid ascent of Grant, highlighting the improbability of his rise and the remarkable shift in his fortunes within a short span.

Mark Twain: A Complex Legacy

[12:18] Ron Chernow:
"Mark Twain is more than just a humorist. He was a sage, a moralist, the conscience of American society."

Chernow introduces his latest biography of Mark Twain, portraying him as a multifaceted figure whose life mirrored the complexities of America itself. The discussion delves into Twain's evolution from a Southerner with antebellum beliefs to a progressive thinker opposing imperialism and racism.

[16:59] Ron Chernow:
"Twain was very outspoken. He wrote against imperialism, defended the Jews, and supported women's suffrage."

Chernow underscores Twain's role as a vocal critic of societal injustices, highlighting his courage to voice unpopular opinions during his time.

Twain’s Personal Struggles and Business Ventures

[22:11] Conan O'Brien:
"He is obsessive, he is nonstop... He would just sometimes stand up, sometimes write at the billiards table..."

The conversation shifts to Twain’s personality—his relentless drive and obsessive nature that led him to numerous, often unsuccessful, business ventures. Chernow illustrates how Twain's inability to let go of his schemes resulted in significant financial losses.

[27:34] Conan O'Brien:
"There's no Airbnb. And shout out to Airbnb."

Conan humorously contrasts Twain's lavish lifestyles and extravagant spending with modern conveniences, emphasizing the impracticality of Twain's financial decisions.

Personal Tragedies and Guilt

[30:24] Ron Chernow:
"Twain couldn't let go of grievances. If you can't let go, the one who's going to end up being victimized by it is you."

Chernow delves into Twain's personal tragedies, including the loss of his children and the strain it placed on his mental health. He discusses Twain's pervasive guilt over events like his brother's death and the impact of his relentless self-critique.

[43:21] Conan O'Brien:
"He convinces his brother to become a steamboat captain... he blames himself for so many things."

Conan highlights Twain’s tendency to internalize blame, presenting him as a figure tormented by his past and the weight of his decisions.

Determinism and Human Nature

[47:21] Ron Chernow:
"Mark Twain said life is a tragedy with comedy distributed here and there..."

The discussion explores Twain's philosophical outlook, particularly his deterministic views where he perceived humans as machines responding to stimuli, questioning the existence of free will.

[50:42] Ron Chernow:
"We have a secret and sincere positions on things, and then we have the positions that we take publicly for our own safety."

Chernow connects Twain’s insights on groupthink and societal pressures to contemporary issues, reflecting on how Twain’s observations remain relevant today.

Controversial Aspects of Twain’s Later Life

[53:16] Conan O'Brien:
"He was having relationships with young girls, which today would be considered disturbing and creepy."

Chernow addresses the more troubling aspects of Twain's later years, including his platonic but controversial relationships with young girls, termed as “angelfish.” He clarifies that there was no evidence of sexual misconduct but acknowledges the discomfort such behaviors evoke in modern contexts.

[59:23] Conan O'Brien:
"He was fascinated with childhood and loved the attention of young women who adored him."

Conan reflects on Twain’s motives, suggesting a psychological component to his interactions with younger girls, while Chernow provides further context on the nature of these relationships.

Twain’s Humor in a Modern Context

[55:55] Ron Chernow:
"Twain is a type of writer almost inconceivable today."

The discussion turns to how Twain’s unabashed humor and lack of political correctness would be received in today’s more sensitive and socially conscious environment. Chernow muses on whether Twain would be "canceled" for his earlier prejudiced views despite his later progressive stance.

[57:58] Conan O'Brien:
"When Twain was alive today, he'd be on the Internet with every conspiracy theory under the sun."

Conan humorously speculates on how Twain's personality and proclivities would manifest in the digital age, blending his historical persona with modern-day behaviors.

Conclusion: The Legacy of Mark Twain and Ron Chernow’s Biography

[64:34] Ron Chernow:
"It’s a privilege to be with you and the whole group today."

As the episode wraps up, Conan commends Chernow for his exhaustive and nuanced portrayal of Mark Twain, emphasizing the biography's impact on understanding not just Twain but also the American zeitgeist.

[64:28] Conan O’Brien:
"You need to read this book because it's not just about Mark Twain. It's also about America."

Conan highlights the broader significance of Chernow’s work, underscoring its relevance to contemporary discussions on American identity, societal values, and historical legacy.

Notable Quotes:

• Ron Chernow [04:34]:
  "I think the question answers itself."
  (Referring to Miranda adapting his book into a musical.)

• Ron Chernow [12:18]:
  "Mark Twain is more than just a humorist. He was a sage, a moralist, the conscience of American society."

• Ron Chernow [16:59]:
  "Twain was very outspoken. He wrote against imperialism, defended the Jews, and supported women's suffrage."

• Ron Chernow [30:24]:
  "If you can't let go, the one who's going to end up being victimized by it is you."

• Ron Chernow [47:21]:
  "Mark Twain said life is a tragedy with comedy distributed here and there..."

• Conan O’Brien [57:58]:
  "When Twain was alive today, he'd be on the Internet with every conspiracy theory under the sun."

This episode offers a profound exploration of Mark Twain's life through Ron Chernow's expert lens, blending historical analysis with personal anecdotes to present a comprehensive and engaging portrait of the American literary giant.