I am not really that old and I have a wide spectrum of musical tastes, but lets post our oldest album. I own more than 300 CD's and 100 record albums all the way up to the year 2002. Lets go with original release date. An album could have been remastered and rereleased in the 90's. The oldest album I own is a CD from an record that was originally released in 1957. Frank Sinatra 1957 Album "Only the Lonely" Its a bunch of mellow suicide type songs. I play it once in a while after a breakup or depressed.
Hmmm. Mine aren't that old. Probably Iron Butterfly's "In A Gadda Da Vida" from '68. I also have BB King's "Live From the Cook County Jail" which might be older, I'm not sure. Come to think of it, I have lots of Beethoven from the 1700's, does that count?
The oldest recording I own is some 1920s jazz on a Capitol re-issue. The oldest album I own is probably Birth of the Cool (1950).
I have the 'Gershwin Plays Gershwin' CD where piano rolls he 'recorded' as early as 1916 have been transfered to a computer-driven piano.
I own a number of 10 inches of Xavier Cugat and Eartha Kitt which I think are pretty old, the early 50s at least. And some old Ink Spots records that are at least that old. I also own a full album (i.e. a huge "photo album" type book of 12" discs) of Glen Miller recordings that I believe is from the 40s, but that might be a re-pressing -- I'd have to check. My brother has a ton of 78s that are from the 30s. But, like Obie, I have several recordings from the 20s, but no actual discs from the 20s. And really, when you get down to it, aren't we all a little like Obie....? (as an addendum: The other oldest record I own, -- the very first record I bought with my own money that I actually still play -- is the Beat's "I Just Can't Stop It.")
I also have an original of Iron Butterflys classic album. I have a bunch of 78's from my grandparents, but I couldnt tell you who is on them.
"The Voice of Komitas Vardapet" an album recorded in 1912. It is sacred Armenian chant and secular songs sung by Komitas.
You're question got my curiosity going. I'm not much of a jazz fan but I do have a sampling from its history for the sake of giving my CD collection an encyclopedic tone. After a brief check, I found a Jelly Roll Morton recording from 1926 off of the compilation from Ken Burn's documentary.