Songs from the 1920s; what about The Prisoner's Song by Guy Massey
© 1924 by Shapiro, Bernstein & Co., Inc.

Oh, I wish I had someone to love me,
Someone to call me their own.
Oh, I wish I had someone to live with
'Cause I'm tired of livin' alone.

There are some Jimmie Rodgers songs too;
Blue Yodel No. 1 (T for Texas) was recorded in 1927.
In the Jailhouse Now" was recorded February 15, 1928.

Bye, Bye, Blackbird is a song by composer Ray Henderson and lyricist Mort Dixon was first recorded by Gene Austin in 1926.