Podcast Summary
Podcast: Conan O’Brien Needs A Friend
Episode: Tom Holland and Dominic Sandbrook of The Rest Is History
Date: October 20, 2025
Episode Overview
This episode features Tom Holland and Dominic Sandbrook, the acclaimed historians and co-hosts of the phenomenally popular podcast The Rest Is History. Conan, an avid listener himself, engages the duo in a conversation that ranges from the joys and absurdities of history podcasting to the quirks of British and American culture, and the importance of humor and perspective in retelling history. The episode is filled with Conan's signature wit, playful transatlantic jabs, and sharp insights into how people relate to the past and present.
Tone: Charismatic, irreverent, intellectually playful.
Key Discussion Points & Insights
1. Conan’s Admiration and Podcast Jealousy
Timestamp: 08:25–09:56
- Conan confesses his addiction to The Rest Is History, declaring, “I have to concede that you have the greatest podcast” (09:11, Conan).
- He jokes that meeting Tom and Dominic is as exciting as meeting George Harrison or Paul McCartney.
2. Humor as a Lens on History
Timestamp: 10:12–13:12
- Conan: Praises The Rest Is History for combining scholarship with comedy, especially discussing grim topics like WWI.
- Dominic counters: “The story is the way in always. And the characters, but the humor emerges naturally. So we don’t try to impose the humor on the story.” (11:24)
- Tom expands: “There’s a case for seeing the whole sweep of human history as a very dark comedy, because history essentially is the record of people not getting what they want...” (12:03)
3. British & American Obsessions: Facial Hair and Stereotypes
Timestamp: 13:26–17:06
- Playful banter about generals’ beards and how Americans “had great beards” during the Civil War, with Conan saying, “I’m not going to sit here and listen to you run our beards down.” (14:33)
- Discussion of historical figures’ vanities (e.g., Custer’s hair loss).
4. Why History (and Its Personalities) Still Matter
Timestamp: 26:40–32:59
- Talk shifts to historical heroes: Nelson cited as a favorite, and Dominic confesses a “torn dress...for Richard Nixon. I like Richard Nixon. I find him very entertaining.” (27:05)
- Conan shares a story of Nixon watching and enjoying his first TV episode, quoting Nixon: “I like it. It’s madcap.” (29:41)
5. Relating to History’s Larger-Than-Life Figures
Timestamp: 32:13–39:35
- Discussion of Churchill’s complexity and Churchill-isms.
- Tom: “The further back in time you go, the harder it is to relate to people because they are so different.”
- Admiration for Abraham Lincoln—“the one figure that is more impressive the more I learn about him.” (31:07, Conan)
- Playful debate on Mary Todd Lincoln (“she was a monster”—Dominic 31:33; Conan pushes back).
6. British Political Icons: Thatcher and Churchill
Timestamp: 33:33–39:48
- Debate on Thatcher’s reputation in Britain; Dominic details, “She was a very strident and partisan politician... she feels she has to become harder than hard to prove that she’s not a soft and sensitive woman. All of which maybe makes her quite unlikable.” (35:58)
- On Churchill: Tom and Dominic credit his singular historic contribution—refusing to appease Hitler in WWII. “He got one massive thing right, and I think essentially that cancels everything he got wrong.” (37:21, Tom)
7. History’s Value: Perspective Over Doom
Timestamp: 44:57–50:01
- Conan: “The role that history plays for me... is it often reminds me that we’ve been here before and that the history of mankind is a lot of things constantly going wrong...”
- Dominic: “Most people alive today live longer, healthier, more comfortable, warmer... all of that kind of thing. That’s not to be complacent, but you’d rather be here than at any previous point in history.” (45:51)
- Tom: “The other thing is dentistry... and antibiotics.” (46:18)
8. Music & Pop Culture: Beatles vs. Stones
Timestamp: 50:01–51:07
- Conan presses the ultimate British pop question:
- Tom: “Beatles. 100%.” (50:14)
- Dominic: “Stones.”
- Conan: “Well, I have to tell you, Dominic, you’re wrong.” (50:17)
Notable Quotes & Memorable Moments
On Podcasting and Ego
“For a while, I believed that I had the greatest podcast in the world...And then one day...I heard someone mention this podcast called The Rest Is History. ...I have to concede that you have the greatest podcast.”
— Conan O’Brien (09:11)
On the Comedy of History
“Even the very darkest episodes, it’s a comedy in the sense that Dante wrote the Divine Comedy. ...Sometimes you have to laugh so that you don’t weep, I guess.”—Tom Holland (12:03)
On Living with History’s Flaws
“He got one massive thing right, and I think essentially that cancels everything he got wrong.”—Tom Holland on Churchill (37:21)
On British Self-Parody
“She was a very strident and partisan politician... she had very little sense of humor and she was harsh, you know, hard company. Difficult company.”—Dominic Sandbrook (35:58)
On Living Through Historical Catastrophes
“You think you’re doom scrolling?...Remember there’s not sand in your bread.”—Conan O’Brien (47:47)
Segment Timestamps
- 08:25–09:56: Conan’s history podcast fandom and humility/humor about podcasting
- 10:12–13:12: Discussion about humor in history and Blackadder/Python influences
- 13:26–17:06: Beards and British/American stereotypes
- 26:40–32:59: Favorite historical figures, Nixon anecdotes, and animatronic presidents
- 32:13–39:35: Relating to “scary” historical personalities, Lincoln, Mary Lincoln’s reputation
- 33:33–39:48: Thatcher, Churchill, political legacy in Britain
- 44:57–50:01: History’s value—perspective, comfort, progress, and not romanticizing the past
- 50:01–51:07: Beatles vs. Stones debate
Chemistry & Banter
- The episode excels in spirited, friendly antagonism—challenges over beards, pudding, musical taste, and Anglo-American quirks.
- Conan expresses genuine fanboy energy, recalling details from dozens of The Rest Is History episodes.
- Tom Holland and Dominic Sandbrook balance erudition with self-deprecating wit, holding their own against Conan’s rapid-fire jokes.
Closing Thoughts
This episode offers a whirlwind, joyous dive into history, humor, and the power of narrative to shape contemporary perspectives. Whether debating the merits of Mary Lincoln’s spoon theft, poking fun at Churchill’s own bombast, or reassuring anxious listeners that “things have been much worse,” all three remind us that history is not just the study of the past, but a vital means to make sense of the present—with laughter, humility, and copious references to facial hair.
Essential listen for:
- Fans of irreverent history
- Lovers of comedy with a brain
- Podcast listeners fascinated by British-American differences and synergy
Further Listening
Recommended Segment:
History’s Value: Perspective Over Doom (44:57–50:01)—for a timely, encouraging discussion about how history can help us cope with the sense of crisis in the modern world:
“Most people alive today live longer, healthier, more comfortable... That’s not to be complacent, but you'd rather be here than at any previous point in history.” (45:51, Dominic Sandbrook)
Don’t miss:
The Beatles vs. Stones clash (50:01)
Banter about pudding and beards (13:26–15:33)