My partner has a recording of the last of the “castrati,” recorded around 1902-3. I have heard it only once, and definitely do not want it on my iPod.
And I have recordings of Florence Foster Jenkins, which are . . . um . . . timeless.
Bix Beiderbecke’s “At The Jazz Band Ball”, and then probably “Potato Head Blues” by Louis Armstrong and His Hot Seven.
In my rotating collection it’s a Glen Miller recording of In the Mood from 1942 or 1943. On my mp3 player right now it’s Ray Charles’ original version of What’d I say from 1959.
“Alexander’s Ragtime Band” by Billy Murray, recorded 1911.
“El Capitan” by Sousa’s Band, recorded either 1902 or 1912.
I have several of the above, like Abbot and Costello and Groucho, but I think Ms Boods wins the thread.
I was hoping some of my national anthems (a few on Edison wax cylinders from the WWI era) would win, and a few of anthems of countries that haven’t been around for a very long time (including the anthem of Nazi Germany, about the age of some of the contenders here, and obviously not made since 1945), but no luck.
I’ve piano rolls of some of Rachmaninoff’s preludes, recorded by the composer . . . but unfortunately there’s no date on them.
The songs on the “Essential Glenn Miller” CD were recorded from 1939-1942. So that is my oldest. Thought I had a version of “Rhapsody in Blue” with Gershwin playing piano, but don’t see it.
A piano and whistle (i.e., human voice whistling) rendition of the main waltz from Franz Lehar’s “Der Graf Von Luxemburg.” My Hungarian CD liners say it’s from 1919.
We listened to him in our History of opera class. “Warbly old lady from my church choir” is the image that it keeps invoking. 
You must mean this: http://en.wikipedia.org/wiki/Phonoautograph
Frank Crumit singing “Abdul Abulbul Amir”, apparently recorded in 1927.
Funny, that’s what comes to mind when I think of Florence Foster Jenkins. :eek:
I still have some songs from 2009.
My oldest is a vocal selection from The Barber of Seville, on a Sony Greatest Performances classical collection, recorded in 1903.
There are also a couple of WWI-era greatest hits, including How You Gonna Keep 'Em Down On The Farm, which would have driven me crazy if I’d had to hear them all the time when they were popular.
Skillet Lickers from '27 is oldest at moment.
I only have a 1GB thingy but I do have some of these on there as of a week ago or so – spun them for a friend from the CD versions two days ago. I thought they were done sometime in the early 1950s, but it’s interesting to hear they were in fact from 1938. Sound is tolerable to me and the piano is better than great.
So, same.
I loves me some Jelly Roll (although he was a braggart and badly overstated his role in “inventing” jazz). The man could play. See here: Jelly Roll Morton - Wikipedia
I’ve been listening to him since before I could even play, and he was a big early influence, but I never realized until I re-listened to these tapes where James Booker and Dr. John and Allen Toussaint and Lloyd Glenn and everybody else from New Orleans got (lifted?) a bunch of their stuff. Very modern playing.
Love Lomax prompting at one point to keep ol’ Ferd going until he can get that whiskey to him. Sounds like they mic’ed a piece of plywood under his feet, as well – I don’t know how he can play so far behind the beat and still keep the time with his foot (and ear, evidently) so consistent. That’s a trip that you mentioned these sides in your OP – I wouldn’t have even guessed these were the oldest on my mp3 player unless you’d mentioned 1938 as the recording dates. Didn’t know he died in 1941, either – thought he lived into the early 1960s.
Probably “This Land is Your Land”-W. Guthrie