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Conan O’Brien Needs A Friend

Ron Chernow

Thu, 5 Jun 2025

Description

Writer and journalist Ron Chernow feels very warmly about anyone who has won the Mark Twain Award for American Humor, including our friend Conan. Ron sits down with Conan for a deep dive into the life of Mark Twain, touching on Twain’s mercurial personality, his affinity for oddball inventions, the unique relationship he shared with his wife, his obsession with Shakespeare’s true authorship, and much more. Check out Mark Twain by Ron Chernow here. For Conan videos, tour dates and more visit TeamCoco.com.Got a question for Conan? Call our voicemail: (669) 587-2847. Get access to all the podcasts you love, music channels and radio shows with the SiriusXM App! Get 3 months free using this show link: https://siriusxm.com/conan.

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Transcription

Chapter 1: Who is Ron Chernow and what is his background?

3.24 - 18.374 Ron Chernow

Hello, my name is Ron Chernow. And I feel very, very warmly about anyone who has won the Mark Twain Award for American Humor. Oh, wow. Including our friend Conan O'Brien. So it's a delight to be here.

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18.514 - 19.595 Conan O'Brien

Thank you very much. Yeah.

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22.284 - 40.723 Unknown Speaker

Fall is here, hear the yell Back to school, ring the bell Brand new shoes, walkin' loose Climb the fence, books and pens I can tell that we are gonna be friends Yes, I can tell that we are gonna be friends

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41.656 - 68.007 Conan O'Brien

Hello and welcome to Conan O'Brien Needs a Friend. This is kind of a special episode. You probably know I'm a huge history buff, and I have read every single book that this gentleman has written, I believe. If he has another book out there, he might have written a Nancy Drew mystery that I'm Unaware of. But other than that, I think I have read all of his books. His latest is a joy.

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68.868 - 97.108 Conan O'Brien

My guest, of course, is a Pulitzer Prize winning author. And his latest biography, Mark Twain, is out now. And Twain, in my opinion, is more relevant at this moment than ever before. And we need Twain. And I'm just thrilled that this gentleman is here today and that he's written this magnificent book. Ron Chernow, welcome.

101.071 - 112.92 Ron Chernow

I saw in your resume, Conan, that you had studied history at Harvard and I had studied literature at Yale. So you were in training for my career and I was in training for your career.

112.94 - 135.716 Conan O'Brien

I know, I know. So all this history that I've done. You want to trade? You want to trade? Sure. Sure. You've done, you know, I've noticed something, which is there's a, and other people have pointed it out as well, that you have written this string of spectacular biographies. And I congratulate you on the Mark Twain. I read all, I believe, 1,200 pages of this book and was enthralled. I love it.

135.776 - 158.486 Conan O'Brien

And I learned so much about Twain that I didn't know because you've unearthed some amazing stuff about the man. And to see his life, I mean, it's very hard to contain this guy's life. And I think you have managed to do that brilliantly. Thank you. But I was looking at your work because I believe I have read all of your books, which I can't say to many people. Judy Blume.

158.986 - 182.361 Conan O'Brien

But it's you and Judy Blume. But there's an interesting path to the order in which you wrote because you start out and you write about J.P. Morgan. and great Gilded Age industrialists, which then got you interested and whet your appetite for your next book, which is Rockefeller, which then got you interested in finance.

Chapter 2: What is the significance of Mark Twain in American literature?

1222.515 - 1237.371 Conan O'Brien

He's so good at seeing the vanity in other people. And then he goes off and does the stupidest things you can imagine. Like, again, you just think he's driven. He can't stop himself in good ways and in bad ways.

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1248.024 - 1267.65 Ron Chernow

He writes a letter at one point to his family. He says, I have to move, move, move, exclamation point. And there is something driving him. I mean, one of many contradictions of Mark Twain is he always described himself as lazy. But we know Tom and Huck in the Mississippi. He published two dozen books in his lifetime.

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1268.15 - 1287.034 Ron Chernow

somewhere between 1,000 and 2,000 magazine articles, filled up 50 notebooks, gave thousands of interviews, gave thousands of speeches. And I, of course, had to go through all of this. And he was very aware of his own nature. He said, my emotions veer from one extreme to another.

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1287.054 - 1306.631 Conan O'Brien

To me, would you suspect, I mean, today... Today, someone would say, you need to go see a psychopharm, psychopharmacologist. I mean, most great men in history would probably be told, you need to be on Prozac. Let's put a little lithium in your coffee. Let's do something.

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1307.151 - 1325.196 Ron Chernow

Yeah. And I mean, there was it was interesting because there were a lot of characteristics. He was, you know, he claimed that he was lazy, but then he would go through kind of this hyper focused period. He could be very scattered and disorganized, particularly before he met his wife, who really cleaned up his people.

1325.216 - 1325.296 Unknown Speaker

Yeah.

1325.636 - 1345.751 Ron Chernow

You know, people would walk into his room and there would be, you know, scraps of writing everywhere. There'd be, you know, pipes and cigars everywhere. It would be a complete mess. I did describe this to a psychiatrist friend who immediately said, you know, about attention deficit disorder. I try not to use contemporary psychological language.

1345.831 - 1366.204 Ron Chernow

It seems inappropriate to project that, you know, back into the past. But there's something like that, you know, that's clearly going on. But I got very fascinated by the business investments. In fact, at one point in the book, I said it was sometimes hard to tell whether Mark Twain was a literary man with business sidelines or a businessman with literary sidelines.

1366.264 - 1391.64 Ron Chernow

He said, I have to speculate, such being my nature. He admits late in his life, after he's lost several fortunes, he said, I was always the easy prey of the cheap adventurer. And there was something very, very compulsive about the speculation because the tragedy of the story is, you know, here's a man who made a fortune in book royalties. He made a fortune in lecture fees.

Chapter 3: How did Twain's early life influence his later works?

1546.918 - 1575.54 Conan O'Brien

He hated, hated Gilded Age millionaires, desperately wanted to be one and did everything he could to be wealthy. He had a publishing house, the typesetting machine, these crazy board games, all of it fails. But he's this kind, generous, there's so many stories of his kindness, his generosity, his sweetness of nature. Yet when he decided to turn on you, He... Forget it.

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1576.22 - 1594.768 Conan O'Brien

He was... His rage knew no bounds. And the language that he used when he decided... I mean, these are people who you said, like, this is the greatest person I've ever met. This Matt Gourley is the greatest person I've ever met. I love Matt Gourley. I love... You know, he's great. He's my best friend. I love him. He's fantastic. And then... And I've experienced this.

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1596.529 - 1598.43 Conan O'Brien

One little... Can we just end here? No, no, no.

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1598.51 - 1601.431 Conan O'Brien

Just please... You can. You can edit this for yourself and play it.

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1601.611 - 1601.911 Conan O'Brien

No, no.

1601.971 - 1627.351 Conan O'Brien

But then... But then whatever the friend did that he decided was, you know, some kind of breach or lapse or any he that snake, that monster that, you know, that lower than low. And he would just he couldn't. he couldn't contain himself. There was no gray area. There was no gray area.

1627.371 - 1637.497 Ron Chernow

No, he couldn't get it out of his system. You know, when he was a young writer in San Francisco, he was about the same age as Bret Hart. Remember Bret Hart, the outcast of Poker Flash? Yep, yep.

1637.517 - 1638.858 Conan O'Brien

Who was the celebrity at the time.

1638.898 - 1658.668 Ron Chernow

Who was the celebrity at the time and who Mark Twain thought was the most celebrated, maybe the greatest, you know, writer of the time. They became very, very close friends. They later collaborated on a play, and Bret Hart was having money difficulties, came and lived in Mark Twain's house in Hartford. He said things about the house that Mark Twain didn't like.

Chapter 4: What are some of Twain's most notable inventions?

2061.515 - 2068.282 Ron Chernow

And so he's gone from knowing nothing about this to suddenly imagining that he's going to be the head of a global monopoly.

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2068.302 - 2093.279 Conan O'Brien

Yeah, he really wanted to be, you know, what today we would call a billionaire. He wanted to be a billionaire He wanted to be a financial whiz, which is so crazy because it's what he loved to make fun of, but it's also what he wanted to be. And the second half of his life, or actually the last couple of acts of his life, I mean, to me...

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2094.64 - 2119.605 Conan O'Brien

he is so disillusioned and so dark and we think of twain again i keep coming back to this that we think of him as um this charming you know the the twain you see on stage in one man shows is just this fun scamp and rascal and you know the old riverboat pilot who's got his stories In the end, he is so dark and he's questioning everything.

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2120.025 - 2147.081 Ron Chernow

Yeah, I mean, he says that anyone who's not a pessimist is a damn fool. He actually says there was no life ever worth living. No life was worth living. It was worth living. And he was asked if he would like to live his life all over again. He said, I would like to relive my youth and then drown myself. He made this statement that the... Only gift that God gave to the race was youth.

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2147.141 - 2172.858 Ron Chernow

He felt that everything else after that was bitterness and disappointment. And he's always kind of pining for this lost paradise of his youth, which is why he wrote so powerfully about Tom Sawyer and Huckleberry Finn, which of course has much darker tones to it. But it's a bit of a paradox because he had this adoring wife. He could not have had a better wife than Libby.

2174.84 - 2193.057 Conan O'Brien

And she also, she read everything Twain wrote and would temper him. Maybe not, I mean, but she would remove if she thought anything was a little, you know, oh, that's a little racier. That language is a little, you don't say breeches. You're talking about underwear. Let's take that out. She was very genteel.

2193.217 - 2198.562 Conan O'Brien

She was very genteel, which is a very funny, they were an odd couple in that way, but she was a great partner.

2199.002 - 2227.433 Ron Chernow

Yeah, and actually one of the interesting parts of the story is Twain said when they first met that he, Twain, was a mighty, coarse, rough customer. And she took this man and she really, because he'd come from this little backwater town, she made him presentable in polite society. And he really didn't know how to do it. She helped him with what we would today call the anger management.

2227.453 - 2246.341 Ron Chernow

He had a terrible temper. So he would very often, if he was angry, he would sit down and he would write a very, you know, impetuous note telling somebody off. And she trained him when he did that, not to send a letter, but to stash it in the drawer and wait a few days. And then when he would cool off, and I can't tell you how many letters there are, you know, in his archives.

Chapter 5: How did Twain's views evolve over his lifetime?

3004.045 - 3019.217 Ron Chernow

Well, I'm so curious if you were alive today, if I can get to ask you a question. If I was alive today? That with Mark Twain, there was just no filter whatsoever. There was no kind of political correctness. He really felt as a satirist that everything was fair game.

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3019.837 - 3038.128 Ron Chernow

So that, for instance, you know, when he wrote his first book, which turned out to be his bestselling book called The Innocents Abroad, you know, he went with these tourists, kind of early tourist crews to Europe and the Holy Land. And he's just sounding off on all these things there in Italy. and he's making jokes about dwarves.

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3038.728 - 3058.437 Ron Chernow

He said, you know, if you want to see, you know, dwarves retail, go to Milan. If you want to see dwarves wholesale, go to Genoa. You know, all of these different things. Well, no one today would dare to make these sorts of jokes. And he really felt that the whole world was his, you know, field for humor.

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3058.697 - 3066.18 Ron Chernow

And I wonder how he would function today, you know, where we're much more sensitive, you know, about... offending different groups.

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3066.34 - 3100.972 Conan O'Brien

Well, I mean, I think it's a really interesting area because, as you know, you talk about it a lot in your book, Huck Finn is very controversial. On one hand, Ernest Hemingway said the American literature begins with Huck Finn. And many great writers have said that is the first great, great, truly great original American creative novel. But it's got the N-word in it countless times.

3101.373 - 3134.297 Conan O'Brien

Yet it also is exploring a real relationship between... Jim and Huck and and and Jim is not a cardboard character. And so but and the N word is part of the dialect of that time. But for that reason, a lot of people say it should be banned. It shouldn't be read or the word should be removed. And you think if he were alive today. And he'd be canceled for things he did when he's 20 years old.

3134.317 - 3158.578 Conan O'Brien

I mean, in his personal correspondence, when he's writing about race, before he's evolved. And when I was reading that, I was thinking, we live in this era now where kids go online and do things, say things. And they get tagged. Like, you're the kid who said that. You're the kid that did this. You're the kid that sang that. You're the kid.

3159.879 - 3179.075 Conan O'Brien

And I don't know, you know, there wouldn't be a Mark Twain. He couldn't exist in a world that's keeping account where anyone can say, wait a minute, we just found something in your personal correspondence or in a speech you gave when you were 25. You're canceled. You're done.

3179.375 - 3188.717 Ron Chernow

Yeah, you know, Mark Twain is a type of writer almost inconceivable today. He had no inhibitions. He felt no need to have any inhibitions.

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