How To Fail With Elizabeth Day · Elizabeth Day and Sony Music Entertainment

Elizabeth's New Show: History’s Greatest Fails

April 7, 2026·34 min·2 clips

Elizabeth Day reveals a jaw-dropping date coincidence: Richard III was killed and his skeleton was found exactly 527 years apart, on the same date.

It starts in a kitchen. An old photograph sends Elizabeth back to a 21st birthday party, a family home, a marquee, and the strange map of university friendships. Someone remembers her as Dollar. The detail is funny because it is so specific, and because youth can make one year feel like a huge social gap. Then the episode tightens. The argument moves to Richard III, the Princes in the Tower, and the fog around facts that may never be proved. Certainty gets handled with care. One side sees a ruler badly smeared, buried for centuries, then injured again by the story history attached to him. The other sees pressure closing in. In that version, Richard is less a monster than a political figure trapped by circumstance, fear, and the hard maths of power. Either way, the tragedy stays put. The fun is in hearing both speakers work through the same gaps and come out with different moral shapes from the same broken record. Elizabeth widens the defence, too. She points to Richard as a sharp political enforcer and strategist for his brother, popular in the north, and willing to stand up for common people. The case turns oddly civic. Trial by jury and laws translated into English make him look more progressive than the legend allows. Suddenly the failure bin feels wobbly. What sounded like a settled historical verdict becomes a question about who gets remembered whole and who gets flattened into one dark suspicion. The ending shifts register with a recommendation for Blink, introducing Jake, a survivor of a terminal brain illness brought on by heroin use, along with medical malpractice, true crime, and supernatural elements. That part feels more promotional than essential. The charge is earlier, where memory and blame keep circling the same question: what can be known, and what has to be argued.

As heard by us

A warm, argumentative preview that turns Richard III into a question of reputation, tragedy, and who gets called a failure.

Elizabeth Day's new show is introduced through friendship first: an old photograph, a 21st birthday party, university proximity, and the odd way podcasting can turn a loose acquaintance into a real connection.

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Why you'd press play

A friendly fight over Richard III, with enough warmth to keep you in.

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