Uploaded August 2026 | Updated September 2026, 1 week ago
There was a time when Al Jolson was arguably the biggest entertainer in America.
He conquered vaudeville and Broadway, helped usher Hollywood into the age of talking pictures with The Jazz Singer, became a radio star, faded from fashion—and then staged one of the most remarkable comebacks in American entertainment.
But recordings and photographs leave us with a puzzle: What was it actually like to see Al Jolson perform?
In this episode of The Common Room, we begin with someone who knew the answer: George Burns. Burns saw Jolson in the great age of vaudeville and, decades later, was still telling Johnny Carson stories about the extraordinary effect Jolson could have on an audience.
From there we explore Jolson’s immigrant beginnings, Broadway triumphs, signature songs, The Jazz Singer, radio career, decline and astonishing 1940s revival.
We also confront the most difficult part of his legacy: blackface and the complicated relationship between Jolson, minstrelsy, African-American music and the popular culture of his time. We neither erase it nor allow one aspect of his career to prevent us from asking the larger historical question:
Why did people who actually saw Al Jolson perform never seem to forget him?
Pull up a chair.
The Common Room is open.
Support Chesterton Radio
Chesterton Radio is an independent listener-supported project devoted to keeping great stories, old radio, literature, history, drama and thoughtful conversation alive.
If you enjoy what we’re building, please consider becoming a supporter. Every contribution helps us keep the Little Station on the air and continue producing programs like The Common Room.
Support Chesterton Radio:
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Stories • Ideas • Wonder
Chesterton Radio — The Open Door is always on.
More Al Jolson on Chesterton Radio!
youtu.be/7U6tTJ29Abg?si=nzXbrm6dTKwLmBav
youtu.be/fSAPMxo985I
youtu.be/nsUCHqPV0_g
youtu.be/f2fEmoy71J4
youtu.be/PE4LnxgYjUo
youtu.be/gAvpjoWmy0s
youtu.be/EPNRC1jtwUU
youtu.be/1XZjWfZLTl0
Get full access to CHESTERTON RADIO at chestertonradio.substack.com/subscribe (chestertonradio.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4)
There was a time when Al Jolson was arguably the biggest entertainer in America.
He conquered vaudeville and Broadway, helped usher Hollywood into the age of talking pictures with The Jazz Singer, became a radio star, faded from fashion—and then staged one of the most remarkable comebacks in American entertainment.
But recordings and photographs leave us with a puzzle: What was it actually like to see Al Jolson perform?
In this episode of The Common Room, we begin with someone who knew the answer: George Burns. Burns saw Jolson in the great age of vaudeville and, decades later, was still telling Johnny Carson stories about the extraordinary effect Jolson could have on an audience.
From there we explore Jolson’s immigrant beginnings, Broadway triumphs, signature songs, The Jazz Singer, radio career, decline and astonishing 1940s revival.
We also confront the most difficult part of his legacy: blackface and the complicated relationship between Jolson, minstrelsy, African-American music and the popular culture of his time. We neither erase it nor allow one aspect of his career to prevent us from asking the larger historical question:
Why did people who actually saw Al Jolson perform never seem to forget him?
Pull up a chair.
The Common Room is open.
Support Chesterton Radio
Chesterton Radio is an independent listener-supported project devoted to keeping great stories, old radio, literature, history, drama and thoughtful conversation alive.
If you enjoy what we’re building, please consider becoming a supporter. Every contribution helps us keep the Little Station on the air and continue producing programs like The Common Room.
Support Chesterton Radio:
patreon.com/chestertonradio
buymeacoffee.com/chestertonradio
The Chesterton Radio World
Chesterton Radio:
Live.chestertonradio.com
Listen & subscribe on Substack:
Chesterton Radio on YouTube:
youtube.com/@ChestertonRadio
The Open Door — 24/7 Radio:
Live.ChestertonRadio.com
Jack Benny:
JackBenny.ChestertonRadio.com
Stories • Ideas • Wonder
Chesterton Radio — The Open Door is always on.
More Al Jolson on Chesterton Radio!
youtu.be/7U6tTJ29Abg?si=nzXbrm6dTKwLmBav
youtu.be/fSAPMxo985I
youtu.be/nsUCHqPV0_g
youtu.be/f2fEmoy71J4
youtu.be/PE4LnxgYjUo
youtu.be/gAvpjoWmy0s
youtu.be/EPNRC1jtwUU
youtu.be/1XZjWfZLTl0
Get full access to CHESTERTON RADIO at chestertonradio.substack.com/subscribe (chestertonradio.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4)
