Finding Madison’s Funny Bone (Podcast)

The humor behind those sparkling eyes

In this episode, Jess and I go on a hunt for the often-mentioned but little-documented wicked sense of humor of James Madison, which is said to have made people roar with laughter.

Listen now:

Show Notes:

Before we started recording, I showed these four portraits to Jess and asked her to come up with a few words to describe the subject.

Top left: 1816 by John Vanderlyn; Top Right: 1821 by Gilbert Stuart; Bottom Left: 1833 by James Barton Longacre; Bottom Right: 1829-1830 by Chester Harding

She came up with words like “striking,” “sometimes kind,” “suspicious,” and “awoken by a ghost.”

Those terms track fairly well with how most outsiders viewed Madison. The writer Washington Irving described him as “but a withered little apple john” and one acquaintance said he was “the most unsociable creature in existence.”

It makes sense then than in 2017, historian and author Alexis Coe called James Madison “America’s least fun founding father.”

But maybe they didn’t know the real Madison…which was no easy feat. His friend writer Margaret Bayard Smith said he was “very droll” and made his company “laugh heartily,” but she admitted that this “entertaining, interesting and communicative” man, “had a single stranger or indifferent person been present; would have been mute, cold, and repulsive.”

So we went on a hunt for his well-hidden and weird sense of humor.

Margaret Bayard Smith circa 1829 by Charles Bird King. Fun fact: Margaret Bayard Smith had three “double cousins” who likely shared nearly 40% of their DNA with her. We talked about this and figure skating for almost nine minutes in a delightful segment that was cut due to its extreme lack of relevancy. This conversation can be heard on our Patreon page.

That hunt for his humor includes his abusive college poetry, his weird experimentation with animals and humans, and his special relationship with Thomas Jefferson.

Baroness Frederika Charlotte Riedesel circa 1795 by Johann Heinrich Schröder. The Baroness was reportedly a favorite comedy subject of Madison’s.

One of the best collections of Madison’s humor is an article called “The Mischievous Mr. Madison” by Hilarie M. Hicks which explores some of his more subtle humor and 19th century dad jokes.

We come away with a better understanding of the personality of James Madison (and myself) and we agree that he is definitely not America’s least fun founding father.

Listen now:


Join our Patreon family at https://www.patreon.com/ploddingthroughthepresidents for exclusive bonus content!

The Mischievous Mr. Madison” by Hilarie M. Hicks, Montpelier’s Digital Doorway, March 26, 2020
James Madison by Richard Brookhiser
Forty Years of Washington Society by Margaret Bayard Smith
The Life of James Madison by Gaillard Hunt
Totalus Rankium: The American Presidents Episode 4.1: James Madison Part 1 (a hilarious take on James Madison’s wooing of Dolley.)
What The Least Fun Founding Father Can Teach Us Now” by Alexis Coe, The New Yorker, November 22, 2017


  1. November 24, 2020 / 9:28 am


    I loved this podcast. I knew it was going to be good when the link popped up in my email.

    Madison is my 2nd favorite president, second to my #1…. JQA.
    When researching James Madison for my novel, I wanted to know these jokes by Madison. It’s sad that Margaret Bayard Smith did not record them for us. His poems….wow, very interesting. I used one of them in the novel. Truly an eccentric little fellow.

    I think Smith is correct in saying that Madison looked older than his 90+ year old mother. His life mask shows it. I also would love to know what Madison’s eyes looked like. I reconstructed his life mask shown in my link below. When making a life mask the eyes are closed leaving the eyes to be sculpted by the artist. Like paintings, artistic license comes in to play and we may not know if the eyes on the mask are correct….hopefully close. Madison’s face drooped on one side of his life mask possibly showing a stroke at some point in his life thus adding to his myriad of health problems.

    Thank you again for the podcast….I can’t get enough of James and Dolley…..makes me wish for a time machine. Too bad Madison didn’t have a diary like JQA.

    Life Mask reconstruction of James Madison… See the droop on one side of his face.

    • Howard Dorre
      November 24, 2020 / 10:31 am

      Thank you, Cheryl! And yes – it’s such a shame that the Virginian presidents didn’t keep detailed diaries or preserve their most personal correspondence. I love the digital reconstructions you’re doing, they’re a very cool way to bring these figures to life!

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