I just happened to find again a booklet printed 96 years ago for owners of Edison phonographs. It's called 'The New Phonogram', was published by The National Phonograph Co., and offers a small slice of US culture as people experienced it in November 1907.
The publishers offered a number of new records in each issue. Here are 2 "irresistably funny rag-time coon songs" from this one (the language is theirs):
9684 "If I'm Goin' to Die, I'm Goin' to Have Some Fun" by Arthur Collins {accompanying the description is a nice little silhouette of what is obviously meant to be 2 Black men, one sick in bed and the other a doctor}
This diverting coon song, rendered with all of Arthur Collins' customary humor, relates the illness and recovery of Jim Jackson. Jim caught a cold and instead of taking hot gin fizzes, as his anxious friends advised, persisted in going out to shoot dice. The night was cold as ice and three weeks later James looked feebly at his physician and was told he was going to die. This sad news acted as a tonic to the sick man, for he sat straight up in bed and remarked: The doctor says my days are done, so if I'm goin' to die, I'm goin' to have some fun. How he acted on this and recovered is told in the song. Orchestra accompaniment. Music and words, Geo. M. Cohan.
9695 "A coon courtship" Ado Jones and Len Spencer {again accompanied by an 'amusing' silhouette illustration}
A really funny vaudeville sketch by two of the most popular artists before the Phonographic public, in which Miss Jones introduces the coon song "You've Got to Love me a Lot". Mose is supposed to be "a midget niggah" making love to a two hundred pound beauty who is inclined to doubt his kissing capacity. Susie is a connoisseur at the osculatory game and her creed is contained in the song she sings. Orchestra accompaniment. Music of coon song by John Lowitz.
At least we've progressed beyond that kind of thing!