This is most likely from the 1890's
(sorry it's so small...)
He's s true "hillbilly", he's got the name for it, and he's from rural Kentucky. His records are so few, but each one is a treasure, I have one myself, and I absolutely love it! He was a "one man show" as some would say, as in the 1890's by playing piano, singing and running the machines all at once, recording thousands of brown wax cylinders, and made his living off of selling these records to the Chicago Talking machine Company. He did this from 1892 to about 1900. From 1900 until 1904, he made his famous wonderful Victor records, which are all wonderful and rare! (The piano on many of them sounds like Freddy Hylands by the way!) He often took from fellow recording artists(who he didn't associate with) like Arthur Collins and Len Spencer, which is clear by him doing the things that they were known for doing differently on their records. So by hearing this, he must have not been able to read music very well, if at all. Also because he often improvised lyrics and/or mixed them up several times of records. I would assume(as I'm listening to records by Leachman as I'm writing this) that when Hylands was on the piano on his Victors, that he helped him with the music for it, as Hylands was much more of a master at reading music and transposing the music to different keys and improvising the hell out of tunes!
It must have been fascinating to see Leachman sing with the accompaniment of Hylands, as they were two musical geniuses together to play out to the solemn recording horn and engineers that ran the sessions; The one that i'm listening to as I'm writing this very sentence os a great example of their occasional partnership at Victor and how well it worked:
Hylands misses a few notes in the left hand if you listen to it close enough.
It has been said that Leachman was such a musical genius that it you played a record for him(even a brown cylinder!) he could play the entire accompaniment of the record exactly! He had the most extraordinary perfect pitch, that's basically what that means. But he couldn't read the music. So i'm sure when he was new at Victor and Hylands was his pianist for the day, he must have set the music in his hands and wanted him to sight read it, but Leachman must have told Hylands something like:
"I'm sorry Fred'rick, I can't read this."
I'm sure that that sort of thing must have angered Fred. at first, but then again, two musical geniuses can work things out, doesn't matter what the circumstances are. I have heard alternate takes of the same records by Leachman, and every alternate take is different, the singer, and the pianist(making the possibility of Hylands even stronger). Leachman's records are always very desirable by record collectors, and especially his home recorded brown cylinders. Even though he made thousands of them, only less than 100 have survived to this date, and one is lucky enough to hear a single one. (I have heard two of them)
I hope you enjoyed this!