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This ought to make the CRTC happy. Turns out the first song ever played on the radio was Canadian Content. That's because most historians agree it was Canadian-born pioneer Reginald Fessenden, who played a violin version of "O Holy Night" to a bunch of no doubt bewildered engineers on ships in the Atlantic.
It happened on December 24th 1906, more than a century ago, and it's generally acknowledged to be the first time music was ever broadcast over AM. And because Fessenden was born in Quebec and he was the one playing the instrument, that would likely qualify it as Canadian content.
There's no word on who sponsored that first show, but rumour has it it was My Pillow, followed by a spot for Frank Leo. The following year, CHFI reportedly went all Christmas on Dec. 23rd.
The First Audio Radio Broadcast of Entertainment and Music 12/24/1906
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What's interesting about the famous 1906 Christmas Eve broadcast is back in 2006, James O'Neal of radio world was asked to write an article for the 100th anniversary.
Interestingly enough, there seems to be very little evidence that this broadcast occurred. Fessenden himself, didn't mention it to anybody until 1932.
Fessenden: World's First Broadcaster?: