Elizabeth's New Show: History’s Greatest Fails

How To Fail With Elizabeth Day33mApril 7, 2026

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AI-Generated Summary

In this debut episode of 'History's Greatest Fails,' Elizabeth Day and Dan Jones, longtime friends and fellow history graduates, dive into the controversial legacy of Richard III, exploring whether his reign constitutes a historical failure. The conversation begins with personal anecdotes about their friendship and evolves into a nuanced debate on Richard’s political decisions, particularly his seizure of power after Edward IV’s death and the mysterious disappearance of the Princes in the Tower. Elizabeth argues that Richard was unfairly maligned by Tudor propaganda and Shakespeare, emphasizing his progressive reforms like trial by jury and legal translation into English. Dan acknowledges Richard’s political skill but maintains that his defeat at the Battle of Bosworth marks a definitive failure. They explore how historical narratives are shaped by the victors, with Tudor-era chroniclers crafting a moral tale of Richard as a monstrous usurper. The episode culminates in a reflection on why failures fascinate us—especially Richard’s enduring legacy, resurrected by Philippa Langley’s discovery of his remains under a Leicester car park. The hosts conclude that failure is not just an endpoint but a lens through which we understand history, identity, and the human need to find meaning in tragedy. The episode also promotes both hosts’ podcasts and The Binge, a true crime anthology series. Key takeaways include: 1) Historical narratives are often shaped by the victors and later cultural reinterpretations; 2) Richard III’s legacy is a case study in how failure can be redefined through empathy and revisionism; 3) The discovery of Richard’s body was a modern-day triumph of persistence and serendipity; 4) Failure, when examined deeply, offers profound lessons about risk, reputation, and resilience; 5) Stories of historical failure resonate because they mirror our own struggles with shame, identity, and redemption.

Key Takeaways
1

Historical narratives are shaped by the victors and later cultural reinterpretations, not just facts.

2

Richard III’s legacy is a case study in how failure can be redefined through empathy and revisionism.

3

The discovery of Richard III’s remains was a modern triumph of persistence, serendipity, and public funding.

4

Failure, when examined deeply, offers profound lessons about risk, reputation, and resilience.

5

Stories of historical failure resonate because they mirror our own struggles with shame, identity, and redemption.

Chapters
0:00
2 min

A Friendship Rekindled

Elizabeth and Dan reflect on their personal history, recalling how they met at university and reconnected through podcasting, setting the stage for their intellectual friendship.

2:00
3 min

The Birth of a Ricardian

I think there is something somewhat mystical about the allure that Richard III has for so many people. And I think maybe it's because it's what we all love. It's an unsolved mystery.

Highlight
5:00
5 min

The Political Spiral Begins

Dan outlines Richard III’s rise as a political enforcer under Edward IV and the fateful decision in 1483 to seize power from his nephew, setting off a chain of ruthless choices.

10:00
5 min

The Princes in the Tower: Fact or Fiction?

Even if some hypothetical DNA testing were done on the remains of the princes in the tower... against known family members. And it said, these are definitely the remains of the princes. It still wouldn't change most people's minds.

Highlight
15:00
5 min

Richard III as a Progressive Leader

He also, as we well know when he was king, introduced trial by jury. He translated a lot of laws into English so that people could understand them. And that, for me, speaks of such a progressive leader who existed way beyond way before his time.

Highlight
High-Impact Quotes
We're living in an age that is more, and this is everything that How to Fail and Your Philosophy is about. It's like failure is not something to be ashamed of. Failure is something to learn from and grow from.
Elizabeth Day28:15
Viral: 92.0
Even if some hypothetical DNA testing were done on the remains of the princes in the tower... against known family members. And it said, these are definitely the remains of the princes. It still wouldn't change most people's minds.
Elizabeth Day13:28
Viral: 90.0
Now, isn't that amazing, Dan? Not really the same dates though because of the shift in the Julian Gregorian calendar. You are such a buzzkill. Thank you very much. The point is, time is a human construct but sometimes the universe sends you mysterious messages from the edges of consciousness...
Elizabeth Day32:32
Viral: 88.0
Speakers

Hosts

Elizabeth DayDan Jones
Topics Discussed
Richard III Legacy95%Philippa Langley and the Discovery of Richard III92%Tudor Propaganda90%Historical Revisionism88%The Princes in the Tower Mystery87%Failure as a Historical Lens85%Modern Relevance of Historical Figures83%Shakespeare and Historical Drama80%
People & Brands

Richard III

person

32xPositive

Elizabeth Day

person

15xPositive

Dan Jones

person

14xPositive

Princes in the Tower

other

9xNeutral

Philippa Langley

person

8xPositive

Battle of Bosworth

other

7xNeutral

Shakespeare

person

6xNeutral

Tudor Dynasty

organization

6xNegative

Leicester

place

5xPositive

Elizabeth Woodville

person

5xNeutral

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