Real oldies
I don't know if you can do this with iPods because I don't have one but on my MP3 player you can search for music by the year it was recorded. According to this the oldest music I have on there is Mississippi John Hurt's 1928 sessions which I listen to regularly. However this morning I was listening to some Bessie Smith on vinyl and the sleeve stated that the recordings were made between 1925 and 1930 something.
The Anthology of American Folk Music starts in 1927 because that's when Harry Smith believed that recording technology was good enough to produce accurate representations of music.
I do have one or two recordings that are slightly older (including that French bee in a jar one that was unearthed a few weeks back) on my MP3 player but I can't say I would ever listen to them out of anything other than historical curiosity.
What's the oldest music you regularly listen to and genuinely enjoy?
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1928-30 was the first golden age of recorded music
It's when the record companies found that they could make money out of selling records by artists who had never been recorded before. That's why they sent talent scouts like Ralph Peer down south. At the end of 1929 the stock market crashed and nobody could afford records any more.
I enjoy
old jazz like Jelly Roll Morton and Louis Armstrong. And western swing, Bob Wills etc, which, I believe, begat rock'n'roll.
Re a previous jazz thread
I refer you to Louis Armstrong and the Hot Five/Seven which go as early as 1923. Also Mr Bix Biederbecke of similar vintage, both are regularly aired on the CD machine.