September 29, 2023
Ongoing History of New Music

The Ongoing History of New Music, Episode 722: A History of Bootlegs

I’m sure you’ve heard the term “bootlegger” before. It’s a word that came out of the 1920s during Prohibition when a bottle of whiskey was as illegal as a kilo of heroin.  Naturally, when something illegal is in big demand, criminals and gangsters move in.  And they made a lot of money.

When you had your booze, you had to keep it out of sight. The easiest way was to put your hooch in a curved metal flask and stuff it in the leg of a tall boot–hence the term “bootleg whiskey.”

Bootleg eventually came to refer to almost any illegally manufactured commodity. That included music.  Bootleg music has evolved a lot over the last century and it’s a fascinating story.

This week’s playlist is a little different because we’re dealing with recordings of dubious provenance that aren’t in Rdio’s catalogue. However, here are some songs from artists whose material has been bootlegged plenty of times over the years.

The Ongoing History of New Music can be heard on the following stations:

And if things go well, the show will soon be heard on a few other stations. I’m also looking for outlets in Vancouver, Kamloops, Kelowna, Red Deer, Grand Prairie, Regina, Saskatoon, Brandon, Windsor,  Montreal, Charlottetown, Moncton, Fredericton, and St John’s and anywhere else with a transmitter. Anyone? Anyone want to start a campaign?

Meanwhile, if you want to go really deep into some of this stories, head to, which is the official archive of all things Ongoing History. This is a place for super fans of alt-rock. Hope you can take a look and start contributing to the stories.

Finally, we have the new Ongoing History of New Music YouTube channel. Give it a look!

Alan Cross

is an internationally known broadcaster, interviewer, writer, consultant, blogger and speaker. In his 40+ years in the music business, Alan has interviewed the biggest names in rock, from David Bowie and U2 to Pearl Jam and the Foo Fighters. He’s also known as a musicologist and documentarian through programs like The Ongoing History of New Music.

Alan Cross has 37122 posts and counting. See all posts by Alan Cross

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